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[0:00] Rory O'Malley: You're listening to episode number 55 of Living the Dream with Rory O'Malley.

[0:06] Rory O'Malley: Audition, side job, swimming upstream. Believe it or not, you're living the dream.

[0:12] Rory O'Malley: Hello, dreamers, Rory O'Malley here, your host for Living the Dream. How are you?

[0:17] Rory O'Malley: I'm doing great. I am working. That always helps. You know, that always helps. Like when you're working and you're doing what you love. I, you know, I know it's called Living the Dream, and that really doesn't come from, you know, living the dream when you're working. It's like when you're not working, you're like, oh, I'm living the dream. That's really where that term comes from. Um, and I started this podcast because of the moments where I wasn't working, and I just so happen to be working right now, which is making it a little more difficult to get the podcast out. But I am not complaining because I'm working on a really cool TV show and learning so much. You know, I'm used to a stage, I'm used to being in front of an audience, and this is very, very different for me because I've done TV before, but this is single cam outside a lot.

It's a show called American Princess, and it is produced by Genji Cohen, who does Orange is the New Black and Glow and all these really, really cool shows. So they're just amazing people working on the show. Our showrunner Jamie Denbow, she's big in the podcast world because she had a podcast called Rana and Beverly, and she's amazing. There's just a bunch of amazing women running the show, and I'm kind of in heaven. I'm playing Shakespeare, so I'm quoting Shakespeare, sometimes badly, but really loving it. And I can't wait for everyone to see it. Um, but what's great is that I'm able to still have these conversations with actors here in Los Angeles who I respect for their stage work, but also for their work on TV and film.

This is definitely one of those conversations. Kate Flannery, who is just absolutely a delight. She was on The Office for years, many seasons on NBC's The Office as Meredith, the uh the drunk. I don't know how else to put it. Um, the ginger drunk. So she's close to my heart. Um, an Irish woman. She's amazing. We met at a charity event. I told her how much I loved her on The Office, and we hit it off, and she is such a great performer. She's an amazing singer. She actually has a show with Jane Lynch, and they released a Christmas show and sing a lot, a cabaret show. And they released a Christmas album last year, Swingin' Little Christmas, and they also will be touring around this year, I think for Christmas, and she also has her stage show The Lampshades, her comedy cabaret show.

She's from Second City, she was in the Annoyance Theater in Chicago. She did the real live Brady Bunch. Um, she has done a ton of theater, and her story is so important to me. It's very important to me because she talks a lot about waiting on tables and working on television. And I think it's something that everyone needs to understand is the reality of what it takes in this business. You need to be able to pay your bills, feed yourself, and have the determination to make everything happen. Uh, and that doesn't just mean acting work, it means maintaining a really good side job. And she clearly had one. And she talks about her entire career and how she got to um where she is, and I just really appreciate all these stories. She's also just so funny. So sit back and enjoy my conversation with my very good friend, Kate Flannery.

[4:12] Rory O'Malley: Hi there, Kate.

[4:13] Kate Flannery: Hi, Rory. Thanks for having me over at your place.

[4:16] Rory O'Malley: Thank you. Welcome to Living the Dream.

[4:18] Kate Flannery: I thank you. I am living the dream, and I love that you're acknowledging it.

[4:22] Rory O'Malley: I'm here to let you know that I see you living the dream, I acknowledge it, and I respect it.

[4:29] Kate Flannery: We met, it must have been a year and a half ago.

[4:33] Rory O'Malley: Yeah, I think so, yes.

[4:34] Kate Flannery: At least a year.

[4:35] Rory O'Malley: Yeah, a little bit. Just about a year.

[4:36] Kate Flannery: Yeah, June.

[4:37] Rory O'Malley: It was June, yeah.

[4:37] Kate Flannery: Yeah, so it was in San Francisco.

[4:40] Rory O'Malley: We were doing a benefit.

[4:42] Kate Flannery: Yes.

[4:42] Kate Flannery: Yes. Oh, yeah, that's it. It was a pride, but it was also a Voice for America concert with Seth and James.

[4:47] Rory O'Malley: Yes, Seth Rodski and James Western.

[4:49] Kate Flannery: Yes.

[4:49] Kate Flannery: Yes. So they were putting together a benefit, and I freaked out that you were there because I'm such a huge fan of yours. Uh my I love The Office, and my husband loves The Office because I think I've already told you this. I was a BBC snob at The Office.

[5:07] Kate Flannery: As was I, yes.

[5:08] Rory O'Malley: I mean, it was just it was so good, and there was, you know, and so when it was coming over to America, there were all these, you know, like, ugh, nose in the air, we're not gonna watch that. It'll never compare to the BBC's version. And my husband was the one who was like, get off your high horse. You have to watch this if you want to date me. And we started watching it the entire interesting thing chemistry. So yeah.

[5:31] Kate Flannery: Oh, it's bordering on abusive.

[5:34] Rory O'Malley: But um whatever works for you, huh?

[5:37] Kate Flannery: Yeah, yeah, yeah.

[5:37] Kate Flannery: But um, we it's very special to us because it's that's awesome.

[5:43] Rory O'Malley: I did not, I didn't realize how special that's fantastic.

[5:45] Kate Flannery: Yeah, but it was such a phenomenal ensemble of actors, and you in particular were such a standout for me for many reasons, but also because you're the ginger Irish one, you know. I was like, Oh, that's someone from my family, you know. I was like, okay, yeah, I definitely I get you spotted, you got it.

[6:09] Rory O'Malley: I spotted, I got it.

[6:11] Kate Flannery: Um, so basically, here we we like to go through some different themes. Yeah, one of the themes that we like to talk about is where you got your education and also what the importance of an education in the arts is to you.

[6:28] Kate Flannery: Um, well, I started taking piano lessons at the age of seven. I had already played by ear, but my piano teacher was awesome because she would allow us to take the last 10 minutes of every lesson and let me just play like whatever I was thinking or learning. So she really helped foster my ear and my creativity, and kind of why I always love to go to the piano to sort of, you know, release, but also she was giving me the structure and all the good stuff that you have to have to make all that go to another level, yeah. Um, and then I think when I was 13, I got obsessed with Annie as and I was from Philadelphia, so I, you know, I was, you know, forget about it. Yeah, I mean, there were three of the original orphans in Annie and Andrea McArdle were from Philly, and I there was a huge article. I had a scrapbook that I kept in the record, the double record, or I mean it's not a double record, but you know what I mean? It has like an opening, the album, the LP.

[7:24] Rory O'Malley: Right, right, right.

[7:25] Kate Flannery: Um, and I actually still have it. I still have it. Um, and I used to do all these clippings from the New York Papers and the Philadelphia papers, and they had a vocal coach that lived fairly close to me. And I begged my mother, and she said, Absolutely not, you have piano and you have tap, your sister only has swimming. That's it, we're done. So I proceeded to get a job at my older sister's she my older sister had a job in a Chinese restaurant that was walkable. So I worked one night a week, and I was the bus girl and I would do the takeout.

[7:57] Rory O'Malley: What?

[7:57] Kate Flannery: And that's what I would use to pay for my lessons.

[8:01] Kate Flannery: I did, I did, because that's how badly I wanted it. And then I ended up like eventually learning how to weigh tables there. It was like a bring your own bottle Chinese restaurant that had a lot of white girls working there for some reason.

[8:04] Rory O'Malley: You paid for it yourself.

[8:11] Rory O'Malley: Sure.

[8:11] Kate Flannery: Um, so uh yeah, I was very motivated, and I also understood that even though I was very specific about what I hoped for my ability, I knew I wasn't there. Yeah, I was pretty clear.

[8:25] Rory O'Malley: So I realized like, okay, you actually Okay, you weren't there at a young age.

[8:29] Kate Flannery: Yes, at 13, I was not there, and I auditioned for the local talent show.

[8:32] Rory O'Malley: You were tough on yourself at the time.

[8:33] Kate Flannery: Oh my god, you better believe it. I still am.

[8:35] Rory O'Malley: You better be baby.

[8:37] Kate Flannery: Uh, um, but I think, um, you know, I had auditioned for Al Albert Showcase, which is the Philadelphia um, you know, it was an amateur show once a week that was huge. Yeah, and Andrea had been on it once, and they sort of claimed her, but they didn't really make her famous. She was like, but it was Al Alberts, who was one of the original Four Aces, three coins in the fountain.

[8:56] Rory O'Malley: Oh, okay, yeah, yeah.

[8:57] Kate Flannery: Um, so they had, you know, they it was it was the audition was down in South Philadelphia. I begged my mother to take me. Uh beg by beg it was only, you know, I had to wait for months to get the audition. It was at this huge Italian catering hall called Jana Caters, and Philadelphia's very Italian anyway.

[9:16] Rory O'Malley: Right.

[9:17] Kate Flannery: Crazy hot mic, uh, probably 60 people there at this audition, and we all had a time slot. And my mother said, Oh, there's a cash bar. I'm gonna have a drink.

[9:30] Rory O'Malley: Perfect.

[9:31] Kate Flannery: My strategy was I would sing "Tomorrow." Uh, and of course, there were six other girls that maybe ten girls that sang this, but my strategy was I was gonna be so good that I would they would pick me. Yeah, that did not happen. Uh, although they did pick a six-year-old woman who was uh she had like a plastic, you know, styrofoam bowler and a cane, and she said, play the entertainer.

[9:50] Rory O'Malley: Yeah.

[9:51] Kate Flannery: And she had like this whole sob story. She actually ended up getting on the show. She said she had a stroke and she made herself, you know, she taught herself how to walk again. I did not have a sob story. It was very much like The Voice.

[10:02] Rory O'Malley: Yes, this is like American Idol.

[10:04] Kate Flannery: Like if you don't have a good story. I didn't, I didn't get that part. You know, I didn't get that part. But that's okay.

[10:08] Rory O'Malley: Yeah, that's right.

[10:09] Kate Flannery: So it just, you know. Um yeah, it sounds okay.

[10:11] Rory O'Malley: You remember every detail of this so well.

[10:15] Kate Flannery: I'm uh sounds like you've really moved on.

[10:18] Rory O'Malley: I really have.

[10:19] Kate Flannery: I'll show you.

[10:21] Kate Flannery: Well, it's just an interesting process, I will say. Uh, and it's it's uh yeah, it's but but you but that's the thing about what we do is that those early days, every single room you walk into where you're putting yourself out there. I remember every audition that you can do.

[10:39] Rory O'Malley: Okay, yeah, absolutely.

[10:41] Kate Flannery: Yeah, absolutely. Because it's it's there's this, it really is like jumping out of an airplane every time you don't know if your parachute's gonna open. I just didn't know.

[10:49] Rory O'Malley: Yeah.

[10:49] Kate Flannery: And then like I think I was 15, uh, somewhere between freshman and sophomore year. I'd done the freshman play. I was in like in George M in the chorus, but I did have a song. But then I got to sing in a nightclub with a bunch of comedians in the suburbs of Philadelphia, and I was so hard on myself. I think I cracked one of my songs I cracked, and um afterwards I was like, God, I was so hard on myself. And I remember seeing one of the comedians, she ended up being a writer on Sex and the City, right? Which is crazy, Judy Tole. And I saw her like the next day, and she's like, You were she goes, that was your first time. She goes, You did great. This is a process. Like I didn't understand that it was a process.

[11:26] Rory O'Malley: That it's not just you have it now or you don't.

[11:30] Kate Flannery: Sure, yes. I mean, unless you're Ethel Merman and Gypsy.

[11:33] Rory O'Malley: Right, but not a lesson.

[11:35] Kate Flannery: Not one lesson, she used to brag. They used to crack me up. Yeah. But you know, it really is like kind of understanding the process of how this stuff works. And yes, and I think I of course I was too hard on myself, and I could I but I I feel like I at least knew that having a sense of um somewhere to go in the process was the most important thing because at least I kept coming back. And so actually I would audition for this, these two dinner theaters that were in Philadelphia. Sometimes I take the boss to invite my sisters, and I ended up getting a job my senior year of high school. I was in Bye Bye Birdie, I played Ursula for three months.

[12:13] Rory O'Malley: Amazing.

[12:14] Kate Flannery: Yeah, it was really actually. Ursula's one says, Let's have an orgy.

[12:17] Rory O'Malley: Yes, yes.

[12:18] Kate Flannery: And they gave me the theme song to the movie that was not in the show, so I got to sing Bye Bye Birdie instead of one of the reprises of Get A Lot of Lemon. I very specifically remember not getting in Bye Bye Birdie.

[12:28] Rory O'Malley: Oh, Jesus.

[12:29] Kate Flannery: Yeah, oh, it was rough.

[12:30] Rory O'Malley: It's crazy, right?

[12:31] Kate Flannery: But it was a really fun show to do for a lot of people.

[12:32] Rory O'Malley: So fun.

[12:33] Kate Flannery: I actually went to the show that I didn't get into like two or three times.

[12:36] Rory O'Malley: Oh my God.

[12:37] Kate Flannery: How old were you?

[12:37] Rory O'Malley: Um probably 14.

[12:39] Kate Flannery: Yeah, that's a tough.

[12:40] Rory O'Malley: Yeah, it's tough.

[12:40] Kate Flannery: It is. But I feel like, you know, I also was noticing that, you know, a lot of the girls that were in Annie were quickly transitioning into that weird, like no man's land where they were just at one of my rival Catholic girl high schools.

[12:53] Kate Flannery: You know, I was like, oh, you know, and I saw Oklahoma, I'm like, oh, there's one of the girls there. Oh my gosh, this is crazy. So it was like I definitely had a sense of like whatever this is, it's not forever. And there's a long if you really want the longevity, you're gonna have to put the work in. That was crazy clear to me. Wow. That's that's a really big blessing to be able to know that from early. Absolutely. And part of me was like, maybe I'm not that good, but I'm gonna work hard. Like I felt like I had like a I was starting with a deficit, but I realized you know what you know, that's all you know. I mean, I don't know. Yeah, there are very few Cinderella stories where someone shoots straight to the top, and they usually burn out as I've gotten older.

I realize that's the case. I mean, that's that's the other theme is is is rejection. Obviously, we were just talking about it on the way up here about rejection, which you know, we become so used to it in life in all aspects, but now as an adult, how have you taken your lessons that you learned from early on and how do you deal with rejection now? Is it different? Does it feel different than it's different?

[13:55] Rory O'Malley: Um, but I also think, but it's it I mean, this is the thing. I really do believe that rejection is protection, and the job you don't get is absolutely fine because it's just gonna lead you to the job you're supposed to have. Right. And I think that that's when you work really hard at what you do. I think you have a sense of personal confidence and self-esteem, and I think that that's part of it. And um and I also think I do sometimes push myself out of my comfort zone. So I have I set these crazy weird things for myself that take me forever to accomplish from my own personal thing, and where everyone else might be like, oh she's doing great, you know. And I am doing great, but I also feel like this is I'm an artist first, and no matter how much commercial success I get, it's really important for me to kind of keep listening to my soul and my heart and and kind of you know where I'm led and what scares me and what feels good when I conquer, you know, when I face it.

[14:50] Rory O'Malley: Well, I mean, that's something I talk about a lot is having to make your own shit, having to make your own opportunity, and you have absolutely been doing that your whole career, right? Because I think some people imagine that you get to a certain point and people just keep tapping you on the shoulder and saying, Yeah, you just trust that magic line.

[15:17] Kate Flannery: Yeah. Right. Yeah, and that that you know, and that maybe there is a half a percentage of people in this business where that is true. Sure. But even they would say they aren't getting the things that they want to do, or they're getting, you know, the same thing they did already. Sure, sure. So, how do you keep finding projects or motivate yourself to keep creating new things and opportunities for yourself?

[15:44] Kate Flannery: Well, you know, I've been super lucky because um I I'm of course jumping around a lot, but um when I um you know four years ago, Jane Lynch asked me to sing with her, and uh it was actually like um I it was only gonna be this short run five shows at uh 54 or below and I remember my aunt died about six weeks before, and I was so close to my aunt. My mom had died the year before, so it was like I was and that and my show The Office had just ended. It was like I had a few like things in a row that were like boom boom boom. Yeah, and I I just remember feeling like okay, well, I can throw myself into this, and and it definitely felt like it would became like this healing thing for me because I had not I I never I I've been doing my comedy act, the lampshades with somebody with Scott Robinson for like I mean we've been doing it forever, but literally the last 18 years in LA and a little bit in Chicago before that.

But I feel like this was a chance for me to sing as myself, which I usually make fun of singers. I'm not like you are a singer. I yeah, I but it's taken me a long time to accept that uh uh for sure. Um, because I usually I used to only sing with a wig on. Um now I only sing with a fall on. No, there's nothing wrong with singing with a wig on. I had a white white wig on with curls. But you know what I mean? When you're a character as opposed to when you're you know, so Jane and I got a sort of chance to sort of like kind of create these kind of stage personas, yeah, you know, as kind of heightened versions of ourselves and kind of our of our chemistry, and I was felt like she was kind of like the nun that was wrapping me on the knuckles, and I was sort of like the sheep dog that kept knocking the show over, you know.

[17:14] Kate Flannery: Yeah, um, you know, and so we had this very short run, and then there was so much uh energy around it that um she ended up getting a five piece band. Tim Davis, who was the vocal arranger on Glee, joined us, and then we had like a real show. It became, you know, like a real show because you toured, yes.

[17:33] Kate Flannery: Um yeah, we toured immediately. I think our first gig out of there was San Diego, and then we started doing like Atlanta and uh Alexandria, Virginia, glamorous Alexandria, Virginia, but you know, all all literally all over the country, a lot of performing arts centers, uh Atlanta performing arts, so many great places, and then we actually did the following year after that, we did a bigger tour for like 23 days all all over. We played the Kennedy Center, we played the lyric opera in Chicago, and you know, but it was it was what I love about it is that the process became like it was just very organic, yeah. And she would come up with a song, and I feel like I would try to either create like something else going on during the song, just something like there was just a lot of play, and she she you know, I I might mess around during rehearsal.

She's like, keep that, keep that right. So that that kind of idea that like you can build on something that you can trust yourself and you can trust that you're not gonna lead the audience astray, you know, and that actually you're creating something that didn't exist before, and now it exists, and so we get to play, and then we decided to do a Christmas album uh shortly after that 23-day tour, and then uh that led to uh in this album, which has another life of its own as well, yeah, which is crazy.

[18:46] Rory O'Malley: No, and it's so you were gonna continue to work on that, or you are you can't.

[18:51] Kate Flannery: Yeah, well, we're doing a new show. Jane and I are doing a show with uh Tim can't do it, but and there's only a few people from our um band that can do it. Uh huh. So we're gonna be at the Carlisle for 10 shows. So it has to be a new show. So this is in September.

[19:03] Rory O'Malley: Yes, which people don't realize. Yeah, a lot of times when you go to different venues, you need to come up with a new show because they want to have it particular to their absolutely.

[19:12] Kate Flannery: They want it, yes. They wanted they want to debut, yes, right. They want to premiere, they want to feel like they're special, and that's why you would come to it. You are Carlisle and 54 Below so special. Everyone's special, but it is, but it I remember I was like when I started doing those kinds of shows, I didn't realize, oh, I've gotta like, I can't, I can only do it at that place now.

[19:33] Rory O'Malley: Right. But I mean it's also I guess really great because it forces you to completely re you know get creative again and you know not just rely on what worked before.

[19:43] Kate Flannery: Right, and kind of think like, okay, well, what do we know about our chemistry? What can we kind of, you know, and even if it's you know almost the same, but different, you know, there's or how what how do we push ourselves even past it? So we're we're literally just we picked the songs, but now we we're literally just starting to rehearse. And uh, you know, I I mean I think it's gonna be I think it's gonna be a blast. I know I feel like Jane is a gay, she has really great energy, and and together we really I've learned to trust that like even if we're doing something new that could be awkward, we're gonna go someplace and it's it's not gonna fall, you know.

[20:19] Rory O'Malley: Right, yeah, which is a great feeling.

[20:20] Kate Flannery: Yeah, you guys have a lot of trust in in yourselves and each other.

[20:24] Rory O'Malley: Right, and I almost feel like Jane has trusted me more than I trusted myself because I've never sung so high as I have on the um on the album. And I don't mean on Mary Jane, I mean the notes, man. I'm like, I mean it's that matter of Jesus God, it's insane.

[20:38] Kate Flannery: Yeah, but you I mean it I love hearing I I you are admitting that you're a singer. I hear that, but I know what you're saying because you are a comedian first. Right. So this was like something you have in your back pocket to make the comedy happen. Like something you can throw up on the stage and and say, like, yeah, I can sing too, and that'll get the audience to laugh.

[21:01] Kate Flannery: Right. And I've I've gone into that trap too, especially because a lot of the time if I'm using my voice, it is to make an audience laugh. Sure. So you you kind of feel like, oh, I can I don't want to ever admit to an audience that I actually like singing. Like it's you know like it's supposed to be like a musical.

[21:22] Rory O'Malley: Right, right, right.

[21:23] Kate Flannery: I feel like I always I I have to have a some sense of irony or some something where like don't you know don't think I'm just resting on my singing laurels. I'm not lazy.

[21:32] Rory O'Malley: Yeah.

[21:33] Kate Flannery: Yeah. I'm not gonna sit you yeah yeah this isn't a hostage situation.

[21:36] Rory O'Malley: Yeah but it's funny it's funny right um okay so you've you've collaborated with friends and you've been you've we'll talk more about uh the comedy scene that you came out of sure but uh one of the themes that we talk about a lot is jealousy or comparing yourself to other artists which is I think the whole key to surviving this business is learning how to acknowledge that we all do that and to let that go and to move past I actually like jealous I'm just I'm just kidding. It's a terrible no it's a that's it is a motivating force. It is show you sometimes it's a really intense and like and when I'm around that energy I'm like whoa like I can't yeah well sometimes I mean I've been told no by people before and thought you know what I'm going to prove them wrong and it might take me seven years that they don't remember that audition or they don't remember this but it lives on inside me. And it can definitely be a motivator but sometimes like the jealousy thing it can be crippling if I don't if I'm not yes they say comparison is the thief of joy. So you have to be really careful.

[22:47] Kate Flannery: But but yet, you know, I don't know about you, but I feel like even at a young age, I I would kind of use other people's careers that I admired. Like I want what they've got. So I'll like you kind of use it as a roadmap. Yeah. But then you realize not everybody gets the same thing. Right. It just, you know, so so at some point you can't be stomping your foot about what you don't get because it actually interferes with what you will get. Yeah. Which could be even better. And I have to say, I'm definitely of the late bloomer uh uh cheerleading squad because I am a late bloomer. Even though I've been working all these years, I still feel like I it took me a long time to have my just to be acknowledged on a different level. And um and I feel like the older you are, hopefully the more wisdom and grace you have to go along with it.

[23:33] Rory O'Malley: Yeah. Grace, that's a good word.

[23:35] Kate Flannery: Yeah, she's a good friend of mine that was. Sometimes I lose her phone number, but yeah.

[23:40] Kate Flannery: But I remember um I think I was 30 when I uh was asked to do Valley of the Dolls. I was living in New York, I'd just done a tour for the really Brady Bunch for over a year. But I'd done, you know, kind of we've been doing it for a long time. Uh I was living in New York, and then Tom Booker, who I'd worked with in Chicago at the Annoyance Theater, second city buddy too. Um, he asked me to play Neilie O'Hara for no money in LA. And I was living in New York. I'd been in New York for six months with my crazy ex-boyfriend. And I was like, oh, I gotta do this. I gotta do this. This is like the greatest part. And it was very much like the really brilli real life Brady Bunch, where we just did the movie on stage verbatim.

And and it was slightly heightened, but you don't have to change a word. And what I I kind of call this pre-YouTube theater was kind of the only way to share was to come to the theater and literally it was very rocky horror. I mean, um people yelling. Yes, they would ch they or they would try to beat you to your line. We had a little game sometimes. Um, but it was like, you know, there was this this thing that exists that you better you better treat it right because we know this and we love this. And don't drop the baby. You got your holding the baby. This is our baby, you know. And we did it here in West Hollywood, and and uh it just was like an immediate crazy hit, like really crazy. And then about a year and a half later, we ended up going to the Circle and the Square uh on Bleaker, and uh we played there for four months, and uh we actually had a pretty respectable run for what it was, but it was just uh I but I felt like that experience for me was it was transcendent because it was the first time I was ever on like page six.

I think it was the only time I was over on page six. Um but it was it was like I even though I was part of an ensemble, I felt like I was being acknowledged in a way that I had never been in Chicago or before that.

[25:31] Kate Flannery: Yeah, yeah, yeah. And I was in um uh Interview Magazine on a ones to watch page, which was huge. And unfortunately, when that episode came out, um, when the issue of the magazine came out, uh our show closed unexpectedly very quickly. Uh I was sleeping on couches, I had to declare bankruptcy because I shared credit with this crazy ex-boyfriend. Uh, it was like everything fell apart, and yet here was this one to watch page in Interview Magazine, which was Andy Warhol's magazine. I mean, it was like my mind was like, what? I I can't even comprehend this. Like, what is happening? And it was literally like for me, it became this kind of very almost like a literary journey. Uh, you know, it's it's I end up sleeping on couches for like months, months, embarrassingly months.

And I had like luckily my sister was there. I had like five sets of kids with friends in New York. Yeah, in like in the midnight, you know, mid 90s. It was the show ended like uh right before Thanksgiving uh in 1996. And I just had a few months where I was like, oh my God, I just did not know what hit me. And my ex-boyfriend had sort of um he was he'd sort of interfered with some of my professional relationships too because he was just he it was just one of those one of those relationships that most people talk about in a one woman show. But I wouldn't but it was but it also I realized that I had to be responsible for my part in kind of letting someone in it was such a wild card and sharing too much too soon and realizing like oh no no no no I no I'd rather be alone than be with crazy. Right. And destructive crazy is the worst. But it's very humbling.

[27:09] Rory O'Malley: Yeah and I remember I read during that time I all I did was wait tables I I did my character from the land of shades by myself sometimes at like Caroline's like at least um like every two weeks I would be in front of an audience for that. I play like baby Jupiter down in like Orchard and Staten like on the Lower East Side collective unconscious some of those places and then I would go to Alan on meetings and I'm therapy and that was it like that was my like I just was like I'm I something's really broken and I need to like stop drop and roll because I'm on fire and not in a good way.

[27:41] Kate Flannery: Yeah but yeah I remember I read um all of Angela's Ashes in a bookstore I would like write the page that I would end on because I kept trying to get out of the hair of everybody I was staying with because of the reason my book was so small. And I was like oh my God. And that book really spoke to me because I not only because I'm Irish and my dad owned a bar but I realized like I'm an adult, like I'm not a child. And here's this book of this brave story of his child whose father drinks the rent. This kid has no control over anything. At least I can work, face my face my you know, my issues and clean up my own mess and you know, see what we see where we go from there, you know. So it was a very humbling time.

[28:22] Rory O'Malley: Oh, yeah. I think that um the juxtaposition of being the one to watch in Interview Magazine at that time is it it's like the parallel of that is having an Instagram account now.

[28:40] Kate Flannery: Sure. And social media is basically something that's putting out a version of what's happening in your life. Right. Right. Not it's that's one of the reasons I started this is that it feels dishonest to just be like, here's all the wonderful, yep, fabulous things that happen when you're in this business, right? And not say, I'm sleeping on couches, this is what's happening, you know.

[29:08] Rory O'Malley: Right. Obviously, it's a lot easier to have control over what you look like your life is.

[29:14] Kate Flannery: Sure, sure. Absolutely. Um what do you think of social media and how it's kind of become a part of our business? Do you utilize it?

[29:25] Kate Flannery: I do utilize it. I just did a TV show for Hulu that just started streaming last month with uh we had a couple influencers in the cast, and that was an interesting thing. I mean, I they are almost from another planet in a sense that like you know, there's a high learning curve for just the protocol of being on set, but also just the kind of like what their um their level of sharing is so high. Like I literally walk into a room and they would be streaming, and so I'd be talking, and then I'm like, you need to warn people that I'm streaming. Like I that's an intrusion. Yeah, so I think it's just kind of the sense of boundaries. Like they have a lot of them have no boundaries. Right. And they don't want to have boundaries. And that's what they think is their success. And it very well may be.

[30:14] Rory O'Malley: I like a little smoke in mirrors. Um, you know, I don't know. It's well, a little smoke and mirrors is one thing, but like just having a private life is okay. It's not, I don't think it's smoke and mirrors. I think that there's some the boundaries are going further and further away. And you want I feel like a lot of us are like, do we have to have an Instagram story every hour?

[30:42] Kate Flannery: Right. I'm in bed, I'm I'm driving now to the gas station, you know, and you realize, boy, my dip, my days are real boring. I don't like but it's it's become a part of the business in a way that 10 years ago, I mean, I just never would have imagined that it would be what it is.

[31:01] Rory O'Malley: No, I I would never know. But it's great to get people to come to uh gig to be like, come on down and see the show. So it it has its positive side, right?

[31:12] Kate Flannery: No, absolutely. And I I mean, I think that it is it's a connector, but I think it's we're all still managing, you know, including you know, politics now. I mean, there's so many things that there are no boundaries. I mean, I'm sure Kim Kardashian regrets saying exactly where she was standing or whatever, or about around the water. You know, I mean there's things that like literally will make your life unsafe and and or even emotionally unsafe, or you know, I mean, God forbid, I I would be in high school doing that. I mean, I can't imagine the rejection of like seeing people at a party that you're not invited to.

[31:47] Rory O'Malley: Yeah. Ugh. Yeah. I know. It's that I keep thinking about my teen years and having to deal with all that stuff on social media. What a nightmare.

[31:58] Kate Flannery: Yeah. I can't. I that is that to me is the I mean, I don't know how you navigate that and still without suffering constantly and having to go through such a roller coaster of emotions and and to not really have the emotional maturity to. I mean, I still don't feel like I have the emotional maturity. I'll say things like, how come I didn't get invited to that?

[32:18] Rory O'Malley: Absolutely. It would, it's it's like a human reaction to have FOMO, fear of missing out, you know, or and that goes back to the whole comparing and you know and disparaging. And and the fact that you're just like, I don't know if what my experience of today was uh good enough. And that's crazy, you know. But it's it's uh it's it's something that I think that we all need to talk about a lot more beyond our business. But I think in our business is kind of like made for us to you know terrorize ourselves in our heads, yes, yeah.

[32:54] Kate Flannery: And I think that I know for me, um, it's taken me years to realize that one of my biggest obstacles, and I didn't even realize one I I this is like a new um a new uh acceptance about this, but I feel like anxiety is really uh done a number on me through my life, and I've done pretty well considering, but I realized like wow, like sometimes it really got in the way and I just didn't have the tools to manage it.

[33:19] Rory O'Malley: Right. Not to even identify it.

[33:21] Kate Flannery: Exactly, yeah.

[33:22] Rory O'Malley: Yeah, yeah.

[33:23] Kate Flannery: I I I would definitely agree with that. I think because we we come from very similar backgrounds, uh, you know, Irish cats.

[33:37] Rory O'Malley: No, but you know, like we're we we come from the same kind of like Irish Catholic upbringing.

[33:43] Kate Flannery: You know, where you don't really you're not gonna talk about those things. Just go get keep your head down, get to mass, go to work. You know, a lot of grown horn.

[33:51] Rory O'Malley: Yes. Don't you think you are? Who do you think you are?

[33:54] Kate Flannery: I mean, my mom used to tell me like you should always brag to me. Tell me everything you did in school. Don't tell anyone else.

[34:04] Rory O'Malley: So you know, like she wanted it, but we, you know, that's awesome that she wanted it because I remember my mother made fun of. I mean, I think I came in, like, I got an award in first grade, and and my mother literally would yell out the window, stop bragging, you know.

[34:18] Kate Flannery: Oh wow.

[34:19] Rory O'Malley: Yeah, no, no. My mom was definitely uh, you know, maybe it's single mom only child, like this was it. You know, I'm sure there's a lot of seven.

[34:27] Kate Flannery: My mom was exhausted by the time I was born. Are you kidding me?

[34:29] Rory O'Malley: Oh my god, forget it.

[34:30] Kate Flannery: You're the youngest of seven.

[34:31] Rory O'Malley: I forgot that.

[34:32] Kate Flannery: Yeah, yeah.

[34:33] Rory O'Malley: That's that's I mean, that dynamic is completely.

[34:36] Kate Flannery: It's a wonder I'm still alive. It really is.

[34:39] Rory O'Malley: Show business. It's I mean, but it but it also like you have to fight to be heard in a way right. That like, you know, I'm I'm certain that that has really given you a lot a leg up in this business. That you're not that you know, just to make your voice heard or say something.

[34:55] Kate Flannery: And this is why I'm a bright redhead. Look look over here. Um okay, so uh something else that we talk uh about a lot is um relationships, not in uh in the business, but in terms of I guess I always bring it up because I had to be away from my husband for a year and a half. So maintaining, you know, you talked about having you know a toxic relationship in the past. How do you maintain healthy relationships, whether it's with someone romantically or if it's you know your family or or just friends, you know, the fact that you and you've created so many things with friends, how do you maintain those relationships?

[35:34] Kate Flannery: Well, you know, I uh it's funny. I I whenever I speak to a college uh college kids, like I went to the University of the Arts and sometimes I go back and speak to the students. And I talk about how, you know, when you have something going on that's high-risk situation for you, audition, a show that you're like just opening and it's you're you know, you're every you're giving it everything you got. It may not be the best time to call the one sibling back who is like, you know, who used to say, you're never gonna make it. Right. You know, and uh it's like the just give yourself permission to have a boundary at least for certain times in your process. Because it doesn't mean you don't love them, it doesn't mean they can't be in your life.

But if they're interfering, it's not like I remember like taking a call before an audition. I'm like, this is so stupid. I should be quiet, I should be focused. I can't manage like whatever's going on with their drama, whether or not it has anything to do with me, but then if it does have something to do with me, then I'm totally screwed. Right. So it's like I I think that that it's taken me a long time to but give your just to give yourself the permission to make a choice.

[36:39] Rory O'Malley: To set those boundaries.

[36:41] Kate Flannery: Yes, yes. And that you can talk to them after the day. And maybe you don't have to talk about something if they're not super supportive, or if they don't completely understand and they may actually start kind of like tearing it down, you know, in a way that they may not even mean to, but you have to, you know, we're artists.

[36:58] Rory O'Malley: Oh my god, my my 1940 telephone one ringy dingy. That's right, 1980s. You want to answer phone back to my gosh, go check it, Drupal check. We take phone calls here on Living the Dream.

[37:10] Kate Flannery: But only there's a lot line.

[37:12] Rory O'Malley: That's right. I like I like that ring.

[37:15] Kate Flannery: That is a good phone.

[37:16] Rory O'Malley: Yes, I it's an old literally, it's an old like if I if I everybody anybody breaks it, I'm just gonna hit them up in front of the phone.

[37:22] Kate Flannery: Perfect. Um okay, so let's go back to where you started. You went to you said you went to school that you go back, University of the Arts.

[37:32] Kate Flannery: Yes, I my first two years I went to Shenandoah University and Conservatory in Virginia.

[37:37] Rory O'Malley: I see.

[37:37] Kate Flannery: But then I realized I did not only want to do musical theater because I kind of felt like Andrea Weber sort of killed my category. There really wasn't a second banana funny girl. And I I it was just a weird realization to me. I'm like, wait a minute.

[37:50] Rory O'Malley: This is right, yeah, yeah.

[37:51] Kate Flannery: No, I know what you because like it you look at like Cats and Phantom of the Opera, where's the character actor and that?

[37:58] Rory O'Malley: That makes sense.

[37:58] Kate Flannery: It's like a house.

[38:01] Rory O'Malley: Yeah, you got the one barely.

[38:04] Kate Flannery: Yeah, yeah, yeah, yeah.

[38:05] Rory O'Malley: No, that makes that makes a lot of sense. It's a lot of like power ballads and and pop music, right?

[38:12] Kate Flannery: Kind of invading into Broadway. So you went back to Philly. Was it more of like when did you start getting into comedy? Was it there? Uh, a little bit, although, you know, I was just doing plays and I still did some musicals. Um, but uh and then when I graduated from college, I got into a comedy group. I was auditioning for everything. Like Walnut Street Theater had this great program. I did not get in. I was going up to New York like for the day to audition for all kinds of stuff, and I but I wasn't living there, I was just kind of going and seeing kind of where I belonged. And Philadelphia Theater Company, I remember auditioning for them. And you know, it was I was just trying to figure out my place.

And so there was a comedy group called Comic Relief. This is back in like 1988. And uh like the Robin Williams Whoopi Goldberg? No, they just had the same. No, no, no, that's no, no, it's they had they were around the same time, and they said, we came up with it first. A horrible disclaimer to have on your resume, but there I was. Uh, so I was being honest, but it was still like, yeah. So I had I was with them for I'd say like nine months, and they were pretty mean, uh, kind of brutal. So not for charity and me. Which is how I sort of stepped up my gig. And they had been together for years, and I was kind of like the outsider coming in.

[39:26] Kate Flannery: Um, but when I was um kind of, you know, we were doing regular shows. We had a regular gig, we had a weekly gig for like I think it was like three months at Plays and Players, which is one of the oldest theaters in Philadelphia. So it was kind of a weird gig. Um, but it was it was great for me because I did write some sketches and kind of figure out like my sweet spot. Um and then my aunt who had moved to Chicago in like 1960, she had been there forever and loved it, and she thought Second City would be a good fit, so she sent me a ticket. And so I remember I went to the city. She sent you a ticket to Chicago to check out Second City specifically. Wow. And uh the first night I went, I figured this out uh years, years, years later.

Um, uh the show that I saw, Jane Lynch was understudying for Bonnie Hunt at that show. And Bonnie, because Bonnie Hunt got married that day. Wow, and Bonnie Hunt came back to do the improv set in her wedding dress. No. Totally boning Jane Lynch on the rest of the show. I was like, I don't know what's going on, but I love this. This is insane.

[40:27] Kate Flannery: Oh my God. I mean, you know, talking about like strong women and just like the whole process seemed like really up my alley. And there were so many great people that had studied and worked there. And they had a training center. And I thought, okay, I'll take classes. And I didn't work at a Chinese restaurant. I worked at a Spanish restaurant then, but I was still like doing my thing. And you know, I stayed with my aunt for the first few months and then got an apartment uh with like three other roommates. I'm actually still friends with a couple of those women. So crazy. But my aunt sort of had opened up this whole world. She was very much like Auntie Mame. She was like an art lover and she had a great sense of the channel. Such a rare thing for a family member to no kidding. She really got me. And I feel like it was kind of a surprise because I didn't, I didn't think she, I didn't think she she was. She, she how was she gonna remember number seven?

[41:16] Kate Flannery: Yeah, exactly. Exactly. Exactly. Oh my gosh. But we had such a great friendship, just such a great relationship. I got to travel with her. She really was Auntie Mame, and I could tell her anything. And she just um, you know, I she kind of helped me, you know, kind of figure out some stuff with my mom, and which wasn't as easy. And you know, and I felt, you know, I I didn't want to leave my mom, but I was like, I gotta go. Yeah, go. Um, but Chicago was I I feel like it was such an amazing time. I felt like everything I really wanted to do, I got to do there. Yeah. I was training there at in the training center, which is about a little over a year program, and then you do a level five show. And Mick Napier was our director. He had started this, he was just starting this brand new theater called The Annoyance.

[42:01] Kate Flannery: Right. I got to uh understudy there one night because someone's dad died, my friend Susan Messing's father died. I had to learn a show that had not been written out yet. It was it was created out of improv. So I had like five songs to learn and these scenes where I had to sort of hit these beats. That's the literal nightmare. Yeah, it totally was. And I remember uh Ben Zook walked me through it, and I was like, I don't even know what it was very physical. The whole show was physical because my character got hurt. I had like a bunch of stunts to do. It was crazy. It was called That Darn Antichrist. It was such a funny musical. Uh Faith Soloway wrote the music. Uh Faith is Jill Soloway's sister.

Uh, um, and that she also uh writes on Transparent as well as Jill, of course. Um, but it was like this crazy world that I just like found my and then uh Susan didn't want to do the role anymore, so I ended up like working at the theater, and then I we started doing the really Brady Bunch shortly thereafter.

[42:53] Kate Flannery: I did other shows like was that an annoyance or that? Oh, that was at the annoyance really I came up with this idea to do actual episodes of the Brady Bunch on stage as a as a comment, as like a social comment. It was like awesome. So we had the laugh track, we had the same music, and we're that Jill was or Faith was actually. And that was a really big huge. That was a really big deal. Yeah, yeah. I mean, I I've heard I wish I would have seen it. Yeah, and and this theater was very much like a clubhouse because the there was an apartment built above the theater, and that's where Mick lived. We all had keys. We all were free to come and go. It was a total clubhouse. Sometimes we crash out on the couches, and it was a big um deck outside. So in the summer we'd just be there. I mean, it was it was awesome. It was it was such a an amazing creative time.

[43:38] Kate Flannery: It was imperfect, of course, but it was so special, and there were so many great people that I crossed paths with at the time who were not who you know, we didn't know who they would be, you know. It's crazy. But I remember like, you know, um uh uh Matt Besser and Matt Walsh who started UCB, they were there. I did a million shows with those guys, and John Favreau did Matson the Musical. I was in an improv group with John at uh Improv Olympic, which was another thing we were all involved with. John was a um one of the hosts at Second City, and when you take class there, you can you can sneak into the shows for free if you're taking so I would you know I would see him like four nights a week in the back, sneaking in the back, it's like secret handshake from the distance, you know.

[44:18] Kate Flannery: And you know, I mean, and at the time Steve Carell was at Second City, um, Steve Colbert was there, Nia Vardalos. I mean, all in different casts. It was it was such an amazing creative time. So many great people. Jackie Hoffman was there then. Right. It was nuts. And everybody's doing our thing. Yeah, yeah. I mean, that's that's way more uh than uh college education could ever provide. Absolutely. And I remember I got to audition for the touring company, and I got it. And I was I was like, oh my god, I was like, I have to leave the annoyance, uh, I'm so sad to leave. This is so hard. And then I found out that I got uh moved from this one company immediately to the swing.

[45:01] Kate Flannery: So I I had to learn the part of three companies, three different you know, uh touring companies, and I still got to do the annoyance. So I got when Jill and Faith asked if I want to do the show called the Miss Vagina Pageant, I got to do it at the Annoyance, which was six girls, like actually six women doing an actual parody of uh a pageant, and um uh that became such a cult hit too. And then Lauren Michaels actually came and was scouting for SNL, and he actually that was the one year he didn't scout at Second City, he only considered uh the four of us from the Annoyance. I remember we had lunch with Lauren, a little walk and a whole bit, and they actually had two spots that were opening, so two uh my friends from the cast uh got the part, um, Melanie Hudzel and Beth Cahill.

[45:46] Kate Flannery: Oh, yeah, yes, yeah. So they both got hired, which was so such a head trip. It was wonderful, but it was also heartbreaking, but you felt like you had to be happy for your friend because I'm Catholic. I'm like, what am I gonna do? Like, yeah, don't be mad. I mean, it's so weird. It was a very trippy thing, and Lauren was kind of famous for pitting people against each other. I mean, it's odd to have you know this kind of kind of with someone else, it's very strange.

[46:10] Kate Flannery: Yes. So you're to make it about this dynamic rather than just an individual audition or something to be like, I'm gonna take one of you, not you know, which one will it be? Right. I mean, I guess you know, the from what it sounds like at that environment that it's very it's so can be so competitive that it probably is probably the first way to see what how you deal with that kind of conversation. Sure, sure. And this was before Tina Fey was at SNL, so it was like it was much tougher for the women. Boys club. Oh, it was so tough. And they, you know, and I felt like even though Melanie was on for three seasons, I felt like she basically got chewed up and spit out. I mean, it's really it was kind of you know, there wasn't like a next level waiting for a lot of these actresses. It was really brutal, yeah, really brutal.

[47:00] Kate Flannery: Yeah, um, and I, you know, again, I go back to rejection as protection, but I feel like I don't know if I could have handled that. I I don't know. It's really, you know, because there's this thing, I mean, there was a thing like, well, that was your dream and it's gone, and you didn't get it. Right. And I think it's gotta be even weirder, like, well, you live the dream and look what happened. Not that, you know.

[47:17] Kate Flannery: Yeah. So it's gotta be, you know, it's it's just bizarre. But I I what I kind of learned to reframe, um, because I think it was like a couple years after that. Then um, we've been doing the really Brady Wrench for a while, and then um we were on a big national tour for a year where I was literally on a rock and roll bus for the last six months with Anna Gasteyer. Um, and we played the Kennedy Center, we played like all these huge packs that are like huge, huge, huge. In fact, Jane Lynch and I have done many of the same places and there's a lot of the same like house manager or the sound effect, like literally it's crazy, so crazy full circle.

[47:49] Kate Flannery: But I feel like um again, like I I there was something for me, it just you know, it just is like one of the gifts of kind of taking your time through your career, yeah. So I I wasn't I and I realized that it was actually uh amazing to be acknowledged by SNL because they you don't go after them, they come after you. Yes, you do not knock on their door, they knock on yours, and it's so just to be acknowledged to be in the company, and there's so many people that have you know auditioned for SNL and not gotten it, it's like you just kind of go, okay, well, at least you know they see a light in you, they see something in you.

[48:25] Kate Flannery: And I remember Mike Schumacher, who was Lauren's right-hand man at the time, he'd been there for years. Um, he was with me at the lunch and on the walk, and um I'd seen him through the years since I uh moved to New York and stuff, and then I remember like even waiting tables like a year before I got the office. I saw him, he was having dinner with Tina Fey at the restaurant where I worked, and I didn't even recognize him because I was so it was a little out of sight out of mind, and I was like, and Tina Tina was only a writer on the show at the time, she wasn't really acting, yeah.

[48:51] Kate Flannery: Um, and he said, you know, I just hope you're hanging in there. I said, Yeah, I am. I'm I'm I'm doing my comedy act every week, and I'm in it, and we just did the Aspen Comedy Festival. I'm doing my thing, but just like to have his acknowledgement was so amazing. And then when getting the office a short time after that, which was like you know, 2004, and then we finally started airing in 2005. So this was like, oh my god, I mean, it's like 14 years after this SNL audition. That's a long time.

[49:17] Kate Flannery: Yeah. You know. Um, but to kind of have somebody who sees you through the crowd and goes, hey, I gotta talk to you, even though you're waiting tables and you, you know, I I gotta tell. And he he's he became the um Jimmy Fallon's uh executive producer, now he's uh Seth Meyers executive producer. So I see him sometimes at NBC events and through the years, and uh it's again like those kind of people that have such a clear, wonderful spirit that remind you that or they he certainly reminded me that I'm on the right path, and even if it doesn't look that way to someone else, right?

[49:52] Kate Flannery: That he gets you, yeah, he knows he he's being like keep going. Yes, and he's educated enough and been in it long enough and has no time for bullshit, yes, yeah, yeah. He's not gonna find it. He's not gonna bullshit you. Absolutely. So yeah, I mean, it's just it's so crazy. So every once in a while, like I'll get a tweet from him or come, and I'm like, oh my god, like this is how we communicate now. Um but it's yeah, it's lovely, it's lovely, and that's that's one of the gifts of social media too, is actually making some kind of connection that is based on a real connection, so it's it's kind of a re uh confirmation of just the the journey, and you know, I mean, some people are they will mow people over and they they have a really fast trajectory for what they're doing. I'm I'm not that person, even if I wanted to be, I'm not that person, right?

[50:38] Kate Flannery: And that's okay. Um, but it's important to remember wherever you are in your path, like just really like look at the yeses, don't just look at the no's. Look at the yeses. Can the yeses keep you going? Can you sustain your life, like your career, your heart and soul through through like those yeses?

[50:58] Kate Flannery: Are they enough? And can you create your own yes? Yeah, well, that too. Because I think I feel like that's, you know. I love that story so much. I love that you were waiting tables. And is this the restaurant that you worked at in LA? Yes. Which is a high traffic for a lot of old stars and new stars, yeah. Everybody, everybody was there. A lot, we've talked about I've gone there before, it's not around anymore, but it was a very high traffic place. So you were put in a position a lot of the time there. Great job. Clearly, I'm sure that it like brought in a lot of good money. But you were put in front of people who were working in the business.

[51:39] Rory O'Malley: Oh, yeah.

[51:40] Kate Flannery: So I was in when I would wait on tables, that was one of the hardest parts for me is that, you know, I remember waiting on an agent who told me he didn't want to work with me. That's happened to me many times. And I'm thinking, you know, here I am, you know, serving you your salad, and what does this mean something? Right, right. When in actuality, it doesn't mean shit. It doesn't he that that person I've never saw again. Right, but it sort of demystifies the power that we give other people, yes. And I think that's really important, and it makes you, it makes you look at the whole picture because you become more of an observer of your own life, yeah, in a good way, and maybe not right in the moment, but like it is kind of wax on wax off.

Like, here's your salad, dude. You know, it's like there's we're not gonna have some intense, you know, you're not gonna give me an epiphany, but at the same time, it's like, well, here we are. We're all kicking, and we're still doing our, we're still going on our path, living our dream, like going after the dream.

[52:38] Rory O'Malley: Yeah, yeah.

[52:39] Kate Flannery: Yeah, it's crazy. I remember like a manager that had rejected me, I was waiting on him, but he was laying some real heavy line on some potential client, like, well, we're creating the castle and you're the king. I was like, What says that? I was like, Oh, I'm glad it didn't work out. What a joke, you know. But then I also used to wait on like Billy Wilder, who was in his 90s, and I would wait on him three times a week, and he couldn't pick me out of a lineup. Yeah, I just was writing about this because I presented at the Turner Classic Movie Festival, and I really got to look at this, and you know, when I learned from that, I used to wait on like Ann Miller and Esther Williams and all these old stars, Mincy Gaynor. Oh my god, so many wonderful crazy old stars. And I what I for what I got out of it for me too is that even though they couldn't identify me or anything, like that's okay because that's showbiz.

[53:39] Rory O'Malley: Yeah.

[53:40] Kate Flannery: And when you dream and hope to work with the greats, be specific, just be more specific. But it gave me a thick screen. Not just for your 15% tip, exactly, exactly, right? You're a delightful exchange. I say this all the time on the podcast, though. Like, I am so grateful for my time as a waiter as a temp. I am so grateful because every time I am acting, every time I'm performing, I know how special of a moment that is. Yes, I have so much experience of fighting for that day to happen that I know I'm enjoying it more than someone who's never had to do that.

[54:24] Rory O'Malley: I think you're absolutely right.

[54:25] Kate Flannery: Yeah, that's really well put. If you allow yourself to, again, like there's some people that it's not enough, it's never enough, it'll never be enough. Right. And that's a motivational style. I get it. But I'm not into stepping over people's dying corpse to get where I think I need to be. Right. And I also feel like at the end, you know, it's as you get older, it's like there's a lot more perspective looking back and hopefully just being able to be as present as possible so we don't get we don't not enjoy what we do get. Yeah, because it's not this and it's not that should be this, should be that. Why'd she get that? Why not? You gotta practice gratitude for what you have that day, and that's whether you're waiting on tables or if you're on a hit show on NBC.

[55:13] Rory O'Malley: Yep, this is shame. This is true.

[55:15] Kate Flannery: So we skipped a little around a little bit, but you get from Chicago to Los Angeles, and how I was in New York for six months, and then because I was touring for a year, and then yeah, and I was in New York for six months. Just like I did I was supposed to do an episode of the Jon Stewart show. I did an episode of Conan, like I was, you know, I winning tables, you know, waiting on all the whatever. I a lot a lot of writers. I used to wait on a lot of writers back then, that's six months. But yeah, and then I when Tom Booker asked me to do Valley of the Dolls, I came out to LA to do it, and then the show went to New York, so that was your first time in LA when you did Valley of the Dolls?

[55:52] Kate Flannery: Officially, yeah. I've done the Brady Bunch on and off, and we did the Miss Vagina Pageant in LA for like a month in 1991. So yeah, so it it wasn't, and I think I was out here for pilot season for like two months too. I borrowed Jane Lynch's car back then. Oh my gosh. Wow, thank God I didn't crush it. Um or else we wouldn't be doing a show with Borough this fall. Um but uh yeah, so there was a lot of um, like I said, there was uh yeah, and then New York I had stayed for three years. Um was singing in a band with the guy from They Might Be Giants, John Flensburg and another band called Monopuff.

[56:23] Rory O'Malley: That's so cool.

[56:24] Kate Flannery: Yeah, so we sang a lot of places in the Lower East Side. So funny, had such a built-in audience, and I never felt like I got that next big New York job. And I did one of the uh the one of the first workshops of thoroughly modern Millie, um which was awesome. Priscilla Lopez was muzzy, it was so crazy.

[56:41] Rory O'Malley: Oh wow, for Sutton Foster was involved, or Cheyenne.

[56:45] Kate Flannery: But it was it was an interesting experience tonight. I certainly learned a lot. Then my part got cut, so I had to audition again for it, and that did, but I Harriet Harris had to audition again too. I was like, what the hell? I know crazy. It's such a crazy I get it, but yeah, you gotta do what you got. Yes, apparently apparently. Yes. I've been in I was in workshops of stuff that didn't go and having to audition with lines that I like wrote for them. I think I can do this because I wrote that line and you kept it. So crazy. Yeah, but you know, it's like if you're not willing to put yourself out there and be vulnerable, then you know you're not gonna go very far. But you get you get to Los Angeles. Was it a culture shock for you? Because it's you I had so many friends from Chicago that were already here. Was there already like the second city?

[57:34] Kate Flannery: A little bit, yes. Yeah, there was uh yes, there was a ton of that, which was great, which was I mean, the Tom Booker was an annoyance theater person. That's how so he had started theater go-go here. We also had this um variety show that we used to do once a week called the Beachwood Palace Jubilee. Some so many really, really funny people. Actually, Will Farrell used to do that sometimes before he was super famous, and um, yeah, there was a few, like, yeah, it was just like one of those things where we got to do characters once a week and mess around and such great talent, like really, really terrific people. And yeah, but you you just you don't know, you know, you you don't know, and then um, you know, the thing about when I first started on the office, I wasn't sure what was to become of my character, and I thought, wow, you know, because usually when you get a start.

[58:22] Rory O'Malley: All the characters, yeah, I mean, all of you guys were there and all wonderful.

[58:27] Kate Flannery: And I wanted, I I have to go back. I know what you I don't want to cut you off. No, no, no. But I want to go, I want to understand how you auditioned because you were all so good with that material.

[58:39] Kate Flannery: Well, I will tell you, I uh I auditioned for the pilot for the part of Jan. I did not get it. I did not get the pilot. And then they shot the pilot in February in late August. They called me in for this other part. Um, and it was all I knew about her was that she was lactose intolerant and was divorced. And it was the um the Alliance episode. It was so it was the whole thing where Michael humiliates her with a birthday card. And that's I was lactose intolerant and I'd kill myself, right? That was the line. Yes, yes, exactly. But the whole, like, you know, um, you know, um, what is it? Elizabeth Taylor called she once her divorces back. I can't remember.

[59:19] Rory O'Malley: Yeah, yeah.

[59:19] Kate Flannery: Yeah, crazy. Um, so I had to basically like react to like just take the shot of that constant, you know. Yeah, so I I uh Alison Jones called me in, and she and it was like literally no makeup, like no kidding, like not like New York no makeup, like no makeup, no makeup. New York no makeup. You know what I mean? Yeah, yeah, a little lip, yeah, like a lot little lip gloss and mascara. Yeah, you know, maybe nothing, nothing. They were like, wipe it off, wipe it off. And I remember seeing a few like really talented people I knew from women I knew from Second City, and I was like, I'm not gonna get this. But uh I went in and then I got I didn't have a cell phone at the time, um, because I was too cheap.

[59:54] Kate Flannery: Uh and I I by the time I got home, I got a call to go to Sunset Gower uh and do it again for for just for the camera, and they wanted me to do it again, and then that's and then by the time I got home, I found out I got it. But I didn't know what it was, I didn't know if it was gonna be every episode. I didn't know because they were trying to figure out what to do with with you know the recurring or series regular or what the cast, what the core was so technically there were six of us that were considered guest stars, like Angela and and Oscar and Kevin, right? You know, and Phyllis and and and uh uh Stanley. It's like we didn't we didn't know.

[1:00:27] Rory O'Malley: So um because they didn't know, right?

[1:00:29] Kate Flannery: I mean, it's a writer's room is basically okay. We we just hired these brilliant comedic actors, and we don't really have roles for them yet, right? So, what what are we gonna do? Right, and I have to tell you, like that is a weird place for a lot of actors to be, and evidently, like it's it was a we we actually were told to bring paperwork and be busy at our desks, so they wanted the cameras to improvise. They wanted the cameras to be able to go anywhere, so while they were doing a scene, they might cut away to somebody, but they weren't sure. So we had to be in character all day. It was it was really wild.

[1:01:03] Rory O'Malley: Wait, they wanted you to bring like your paperwork from home, like I was doing like your life insurance form.

[1:01:09] Kate Flannery: I was doing I was doing like my tax work. I was like, all these numbers, I'm like, geez, man.

[1:01:14] Rory O'Malley: What?

[1:01:15] Kate Flannery: Yeah, and I brought like big thick books that I would hide under the other the fake paperwork. I was like reading Ruth Gordon's like whole entire life story. Um, and it was like because they wanted to be able to figure out how they what they kind of called like you know, like the elephant in the wild or something, the animals in the wild. Like they wanted us, so that's kind of how they were developing those those looks. So it was a really interesting process.

[1:01:36] Rory O'Malley: Yeah.

[1:01:36] Kate Flannery: Um, but you know, it's so different because most actors will count how many lines they get in the script. And I got knocked out of that so fast, I stopped doing that immediately because I realized it was only gonna lead to self-destruction. Um just had to trust the process.

[1:01:50] Rory O'Malley: Yeah.

[1:01:50] Kate Flannery: And they really knew what they were doing. They wanted to be so true to the British version that they just wanted to make sure that no one was acting.

[1:01:56] Rory O'Malley: Right.

[1:01:57] Kate Flannery: Like we had to be really present and fully realized as human beings first.

[1:02:03] Rory O'Malley: Right.

[1:02:03] Kate Flannery: Which I think is like such a gift, and I feel like it's something that has really changed comedy. I feel like we were one of the first shows to really own that to be allowed to just say it and not have to perform in a way that was like over the top or something.

[1:02:18] Rory O'Malley: Yes.

[1:02:19] Kate Flannery: I mean, that it's it's just so funny because the office is such a great idea because that is what you know, such a large pro a group amount of people are going to offices every day, and no one had really explored it at all.

[1:02:36] Rory O'Malley: Right.

[1:02:37] Kate Flannery: Especially not in that way, in that honest way of the mundane, hilarious things that happen. And you all did create such a wonderful ecosystem within that set.

[1:02:49] Kate Flannery: Well, I'm so lucky because I feel like a lot of my my storyline got cut the first half of the second season, and I was like, uh oh, I wonder if I'm gonna get fired, or you know, I don't I just didn't know. I was like kind of freaked out about it. And I wouldn't know. My parents would call from Philadelphia, like, we watched the whole thing and you barely talked. I'm like, oh, my whole story, like I kind of like shit. That's how I'd find out. But uh I learned like I don't take the call anymore. Like again, I'm like boundaries, like, I'll find out later. Right. But what I loved about what they did with Meredith in particular was that I got to do so much physical comedy, and even if my lines got cut, I felt like it created this kind of chess game with my character.

[1:03:24] Rory O'Malley: Right.

[1:03:25] Kate Flannery: That I feel like none of the other characters really got because I really didn't step up, I stepped up so slowly that I never felt like I outwore my welcome.

[1:03:34] Kate Flannery: Well, that was actually my first, like, sort of, oh my god, yeah, who is this character? Oh wow, what's happening? I actually got to do the Tonight Show because of that episode.

[1:03:44] Rory O'Malley: Really?

[1:03:44] Kate Flannery: Yeah, it was crazy. That was crazy.

[1:03:46] Rory O'Malley: Why was that?

[1:03:46] Kate Flannery: Uh, I think they just thought it was the funniest moment from the episode. So it was pretty damn funny. Talk about physical comedy.

[1:03:54] Rory O'Malley: Yeah, yeah, it's so fun.

[1:03:56] Kate Flannery: Oh my gosh, crazy, crazy. And our yeah, we had an editor that came up with that move because we initially shot it without that, and he's like, I think this is gonna do it. Dave Rogers, who became an Emmy Award-winning editor from that, he came up with this idea, and one of the producers tried to you can do your own stunt. I'm like, sure. Like, I you know, I'm one of seven kids, like, let's go, let's play. And also, it's fun to be a go-to person when not everybody, I don't know. It just again, it kind of gives you a sense of like, okay, this is my lane. I can stay in this lane. I'm happy in this lane. This is right when you're like a team player and you realize that not everyone is a team player. You're like, oh well shit, I can be the team player anytime.

[1:04:36] Rory O'Malley: Totally, and even though I feel like I've definitely had the feeling of like holding an audience in the palm of my hand, like playing the Elio Hara was like, oh my god, that was like one of the most validating, wonderful, like, oh my gosh, it just tested every sense of my metal. But I'm not Steve Carell. Steve Carell is a genius. That guy, he can do anything, he can memorize anything in a moment. I've never seen anybody so good at what they do and make it look so easy and not make it about them. You know, when the cameras are off. I mean, he's really a remarkable artist, like really remarkable.

[1:05:14] Kate Flannery: So I was like, okay, I'm fine, but I don't okay. Yeah, I know, I know you're like, you're like, I'm so excited to be invited to this party. So I'm gonna like do whatever it takes to make sure. I gotta trust too, and have a sense of trust and be like, okay, whatever I'm waiting for, it's worth the wait. And they really came through for me in such a wonderful way. Oh my god. And I'd never had to have a conversation, or you know, my manager never called. I never was like, you know, right. Not that I wasn't disappointed, but I kept it to myself. I was like, hey, that's okay, you know, it's all right. And then when I did show up, it was like it felt like it had so much more of an impact.

[1:05:49] Rory O'Malley: Right.

[1:05:49] Kate Flannery: That it was really earned that they were really because they were telling a story for each character. Right. And so many times when you work someplace with somebody, you may see them, you may have seen them for four years, but you really didn't talk to them till like something happened, and then like, oh, I didn't know that about them.

[1:06:04] Rory O'Malley: Yeah.

[1:06:05] Kate Flannery: So not everybody comes to the forefront right away in your life. Yeah. Or, you know, maybe somebody reminds you of somebody you don't like, so you don't really talk to them. Like, who knows?

[1:06:13] Rory O'Malley: Yeah, I think.

[1:06:13] Kate Flannery: No, it was so honest and true to what a real dynamic of an office is. And I that's why I'm so intrigued by the casting, because it was like, oh, you're a genius comedian too. You've been sitting back there in the corner for like a season, you know, like everyone had these different moments where I just I couldn't figure out how they came to that.

[1:06:41] Rory O'Malley: But Alison Jones is the greatest.

[1:06:44] Kate Flannery: I mean, I think it's a testament to had you auditioned for her before.

[1:06:51] Rory O'Malley: And I don't think so.

[1:06:53] Kate Flannery: I don't think so. I think it was The Office.

[1:06:55] Rory O'Malley: No, no, no. You know what? I had a meeting with her in like 1993 when she was doing Flying Blind. Because I had a coach in Chicago that was a friend of hers, and she sort of did it as a favor. But I was like, it's okay. It's that funny.

[1:07:07] Rory O'Malley: No, but I just think that it's a testament to going into any audition room and showing what you can do, and then you know, you may not get the immediate result. You have to go back to waiting on, you know, tables.

[1:07:24] Kate Flannery: Well, I kept my job through the first season, which I think I still work waiting working at the restaurant because we only did six episodes the first season, so it was like it was not like woo-hoo, you know, it was like who knows.

[1:07:34] Rory O'Malley: Yeah, yeah. I mean, that's a learned behavior from, you know, past disappointments.

[1:07:39] Kate Flannery: So you kept waiting on tables while it was airing.

[1:07:43] Rory O'Malley: Uh yeah, even the first when the first season started airing too, yeah. And then we had to wait another month to find out if we got picked up.

[1:07:48] Kate Flannery: Wow.

[1:07:49] Rory O'Malley: And I remember, you know, we got a lot of the producers and um, yeah, they would kind of come in, and some of the directors and they sort of some of them were great, some of them were weird about it.

[1:07:59] Kate Flannery: Yeah.

[1:08:00] Rory O'Malley: Um, my main boss, uh Greg Daniels was awesome because he completely ignored the fact that I was wearing a uniform and he's like, I'm so glad I wanted you, I gotta talk to you. You say the word vagina in the healthcare episode. I know you improvise, I'm fighting with it everyone. Really try to give me loved him so much for that. I will never, never. I mean, that was so wonderful.

[1:08:19] Kate Flannery: It was again, it's like we're just on our path. It's like, okay, and this is it doesn't matter exactly where you meet, it doesn't have crazy, wonderful, insane meaning. It's just this is we're all on the planet. I gotta talk to you. Here we are, let's go.

[1:08:32] Rory O'Malley: Yeah, you know.

[1:08:33] Kate Flannery: Oh my god, I love that story so much. I love that you kept that job because you know the value of a good side job.

[1:08:47] Rory O'Malley: Well, I was also kicked in the teeth a few times. I when I first got hired at Second City, I think I quit, you know, Cafe Barber, but I'm like, woo-hoo! And then I realized, oh, I'm not really making that much here. So I was like, oh, okay.

[1:08:58] Kate Flannery: No, I mean, I was telling before we started, I was telling you about my first job in LA was at the Hudson Theater, and you know, I had gotten a job waiting tables at the Wood Ranch at the Grove. And as soon as I got the job, I was like, I'm gonna have to quit. And then, you know, came back with my tail between my legs after I found out it was seven dollars a show, and was like, I'm gonna have to like double up my shifts somehow. I'm gonna because I can't pay for the gas to get there, and you know, so it's you learn your lesson.

[1:09:28] Rory O'Malley: Right, and it's not a punishment to have to work another job sometimes, especially if you're doing something that you really, really want to do, right?

[1:09:34] Kate Flannery: That really speaks to you.

[1:09:35] Rory O'Malley: Yeah, it's not it's not like the universe going, okay, we'll see how bad she wants. It's like, no, I mean, you just learn how to manage a lot and you just do it.

[1:09:43] Kate Flannery: Right. I mean, it's very clear to me that you're the kind of person who can walk into any situation and find the joy, humor, and connection with other human beings. And I think that whether that's the cast of The Office or your fellow servers at the restaurant.

[1:10:00] Rory O'Malley: Right, a K Mandelini, yeah.

[1:10:02] Kate Flannery: You're all people, you're all trying to get through the day. And um, I think that that's an invaluable lesson to learn early on.

[1:10:11] Rory O'Malley: Yes.

[1:10:12] Kate Flannery: Because it's gonna, you know, even after The Office, everything that you go into, you have to like make the most of what the next situation is going to be.

[1:10:20] Rory O'Malley: That's true.

[1:10:20] Kate Flannery: Yeah, yeah, and and so much of like managing your disappointments. I mean, it's just this is such a big part of it all, too. And uh, and I think having a sense of trust in your own process. And uh, I remember my the restaurant manager when I finally gave notice, he said, we were gonna get you a cake, but you'll be back, which is so hilarious. And I was like, I kind of was like, he's got a point, I might, because I other people were like, screw you, man, and then they would come back, you know.

[1:10:49] Rory O'Malley: Right.

[1:10:49] Kate Flannery: So you just you know, it's just I don't know. I mean, and now I feel like I can tell the story because it has a happy ending, of course, but you know, but that's that is that's I mean, I I've when I got my first Broadway show, I knew it was only a six-month contract, and I kept working at the temp office that I had. So I would do, you know, it was a I was an understudy, so I wasn't on every night. So I thought, well, I definitely should keep this job. I'll do the office hours during the day, do the show at night. And it almost killed me. I was really lost, it was too much, it was definitely too much.

[1:11:23] Rory O'Malley: But I once that show ended, I went back to BlackRock Financial, and I was filing and putting together stuff, and the kind of humility that it took for me to like let go of my ego that I was on Broadway right a few months before, and here I am, you know, tempire number two. That was my email.

[1:11:49] Rory O'Malley: Right.

[1:11:49] Kate Flannery: And and it doesn't diminish what you just went through, it doesn't mean like, well, no, and and honest, honestly, I am so grateful for you to share that very specific part of your story because I think it's the most important message we can give to people who are trying to get somewhere in this business.

[1:12:09] Rory O'Malley: Right.

[1:12:10] Kate Flannery: Is that that is part of living your dream. And also I think sometimes people make this grand declaration like, I won't do anything unless I get paid. I won't do theater unless I get paid. And they have a number or something in their head, and that's fine. But that also really limits your possibilities. Because when I first started the Really Brady Bunch, we weren't paid anything.

[1:12:31] Rory O'Malley: Yeah.

[1:12:31] Kate Flannery: Nothing. Right. We got beer and fried chicken at the end of the show. That was it. And it was wonderful.

[1:12:35] Rory O'Malley: Yeah.

[1:12:37] Kate Flannery: And when I first started doing Valley of the Dolls, we didn't make anything. And then eventually, you know, we got to go up Broadway and we had a little something, but it was like, but I kind of trusted that if you're feeling like there's a spark within the project that you're doing and that people are excited about it, that you will get seen in a way that you'll never get seen in some rep company in St. Louis or whatever. It's just not the same. And taking those risks and also kind of trusting that you can this is all part of the dream. It's like it's all part of it. And not getting paid, uh, is actually, I don't know, it's it's almost like how bad do you want it? You know, it's it's a little bit of a um not a test, but it's it's definitely like a it's it's actually like putting your your life in action.

You're taking the action. And so it's your journey's already begun. Your career has already begun. You can judge it or not, but it you're you're in it. You're you're already in it. Even if you're working four other jobs that week, it doesn't matter. You're in your dream.

[1:13:42] Rory O'Malley: Well, this is the official end of the podcast.

[1:13:47] Kate Flannery: That is exactly that that's that's what I'm trying to get at. And I think that you know, like the that coming from someone like you means so much to me. It means so much to people listening because you have been able to accomplish so much and you've worked so hard, but you've done it with joy. And uh I think it's just about finding a way to be grounded and happy while you go through the ups and downs of this crazy business.

[1:14:13] Kate Flannery: I think that really is an important piece. Uh, you know, and I I mean I'm so lucky. My boyfriend, I met him on The Office. Uh, we've been together since he's actually dancing with me in the finale with at Dwight and Angela's wedding.

[1:14:24] Rory O'Malley: Oh, I didn't know that.

[1:14:25] Kate Flannery: He had a line in the scene where they reveal Pam's mural because he's they let him be the photographer in the that's that's amazing.

[1:14:32] Rory O'Malley: So awesome.

[1:14:33] Kate Flannery: You know, I love Chris so much because he gave when you guys came to Hamilton, he gave me a picture of the Golden Girls.

[1:14:38] Rory O'Malley: Yes, he did.

[1:14:39] Kate Flannery: He's just gonna be. So like he's without a doubt my favorite person in the world.

[1:14:45] Rory O'Malley: Well, but it's it's funny because I never expected to get a show in my 40s and also get a fella. So it's like I feel like the world's been revealed. I mean, it's you know, the gods have been very, very good to me. And I and I it's not lost on me. It's really not.

[1:14:59] Rory O'Malley: Well, you deserve every good thing that you get, and I think that you've been giving a lot of joy to so many people. Like I said, whether it's the kitchen of Kate Mandalini's or the side of The Office, I think that you're just a really great person. And I'm so grateful.

[1:15:17] Kate Flannery: Thank you. You're so awesome, and you're so you have such a great spirit because you're so available, and I and watching you perform, because I saw you before I knew you, and I I just feel like there's that's something you can't be taught you can't learn it I mean maybe you can peel away from stuff and get rid of some stuff but you you either got that or you ain't.

[1:15:18] Rory O'Malley: So what you're saying is I'm Ethel Merman.

[1:15:18] Kate Flannery: Um, we should always so lucky.

[1:15:18] Rory O'Malley: Yeah, right, not a lesson, not one lesson.

[1:15:18] Kate Flannery: Thank you very much.

[1:15:18] Rory O'Malley: That means thank you so much really right back at you this and I tell say this all the time I have started this podcast just so I can find the people who I want to spend an hour with and talk to and have a good excuse and you're definitely that thank you so much for doing it. Audition side job swimming upstream believe it or not you'll live in the dream.