Dennis Osborne: Well, I got this excited phone call from him and said, I'm sending you a plane ticket. You've gotta get out here right away. There's this game, we're just going to, just gonna play it. I, it's, I'm not even gonna tell you what it is, justs, get on the plane and get out here. So I flew back there and we played Myst for five straight days without ever getting off the main island.

Barry Joseph: Welcome to Matching... Oh, you know where you are, and what an episode we have today. What. An. Episode .We're gonna focus on Stephen Sondheim's relationship with video games... sort of. This episode is hard to describe. The audio from today comes from a podcast I was a guest on by Dennis Hensley called Dennis Anyone?

So is this just a repodcast? Well, no. This is my own edit of that episode. See, this is what happened. Dennis invited me onto his podcast, then about an hour in his friend joined us. His name is also Dennis. So this episode could be called A Tale of Two Dennis. Let's call him Dennis 2.

It turns out Dennis 2 was friends with Sondheim for around 35 years playing digital games with him. In fact, Sondheim would fly Dennis 2 out from LA just for weekend marathon play sessions of games like Myst and Oxyd. The thing is, Dennis 2 had never spoken publicly about his relationship with Sondheim.

Even when Sondheim sent his biographer Meryle Secrest in the nineties to interview him. He never spoke about his relationship with Sondheim until this podcast episode, and it was pretty remarkable.

Dennis 1 invited me to be both guest and host, so I got to interview Dennis 2 as well. As you know, my book is based on conversations with and information from over 120 people. But other than John Weidman, no one else spoke with me about playing digital games with Sondheim and how it framed their relationship. And no one shared photos with me.

Until Dennis 2. By the way, I'll share that photo in the show notes, and when I put it on my Instagram feed, it received 130,000 views in 24 hours. How? A repost from Lin Manuel Miranda. It has been quite a trip, so please join me as we revisit it together.

Dennis Hensley: Joining me now from New York City. It's Barry Joseph, the author of Matching Minds with Sondheim. Welcome to the podcast.

Barry Joseph: Dennis. I'm so excited to be here.

Dennis Hensley: I love this book because I love Steven Sondheim's musicals, but I also love puzzles and brain teasers, and I didn't know the depth of his passion for them until I read your book.

Um, we've just had a special guest pop up in the Zoom, Dennis Osborne. He's a good friend of mine. Welcome Dennis.

Dennis Osborne: Thank you for calling me a special guest. That's the first time that's ever happened to me before.

Dennis Hensley: You're a total special guest and you were a friend of Mr. Sondheim and you played a lot of different kind of games with him, but, but video games were a big thing.

Dennis Osborne. Talk to me about playing video games with Steven Sondheim and Barry, if you have questions for Dennis as it as it pops up, or like, oh, I, oh yeah, I never knew that or I learned that or what about this?

Um, feel free to pipe in. So Dennis, talk to me about playing games with Steven Sondheim.

Dennis Osborne: It started in the eighties with the Cliff Johnson games, which Barry, I'm sure, knows about Quite

Barry Joseph: yes indeed.

Dennis Hensley: So what was the format? They were like CD rom games or like video, like

Barry Joseph: it was a Macintosh, right, Dennis?

Dennis Osborne: Yes. Macintosh games. Very primitive. Little puzzle games. The first one I believe was At The Carnival. And so every ride had a little word or number puzzle that you would have to figure out before you would get on that ride until you finished it. And then at the end they all sort of coagulated into a major puzzle, all the puzzles you just did.

And that, of course, Steve loved that. Then he did A Fool's Errand-- Cliff Johnson-- did A Fool's Errand and that's when he, Steven Cliff got in touch with each other because there were some things about the game that Steve had questions about. And so he was helping him fix certain puzzles and stuff, but Steve loved Fool's Errand .

And then 3 in Three followed that. I still have these on my computer, actually.

Barry Joseph: Nice.

Dennis Osborne: I have an old Mac that when I'm stressed out, I will go to this Mac and pull, pull those games up and play them because they calm me down and get me able to handle all the stuff that's happening.

Barry Joseph: Just to clarify. I think it was called The Fool's Errand. And

Dennis Osborne: The Fool's Errand. Yeah.

Barry Joseph: And just for anyone who's gonna Google it, and I'm curious if he ever discussed with you how he ended up in the credits for 3 in Three being thanked.

Dennis Osborne: Well, because then Cliff started sending him his ideas for 3 in Three, and Steve would give him suggestions and say, this puzzle would work better this way. He would give him little suggestions and how he ended up in the credits of 3 in Three.

Barry Joseph: That's amazing.

I show a photo of those credits in the book 'cause seeing Stephen Sondheim's name in a video game in the credits blows my mind.

Dennis Osborne: Yeah. And to me it was completely logical because they were always talking about puzzles and things like that.

Barry Joseph: So let me ask you, Dennis.

So Steven Sondheim played, I think his first digital games with the Atari when they came out in the late seventies. And then he got a Macintosh. He actually got a Macintosh 'cause Apple sent him one for thanks for letting him use his name in some promotional materials. So by the late eighties, he was playing games, like The Fool's Errand.

Oh yeah. Oh. But in the early nineties he graduated as many of us did to CD ROMs playing Myst.

Dennis Osborne: And Is ever with him? Well, there was, there was one in between there. That's not in your book, actually.

Barry Joseph: Tell me .

Dennis Osborne: That- I was surprised- called Oxyd, ah, OXYD by Dongleware, a German company. And that he was obsessed with, he was absolutely obsessed with, and they kept coming out with more and more ornate puzzles and larger games.

He would have me, you know, fly out there because he would get stuck in something and he would say, I just have, I just have to, you have to sit here and help me through this. Talk me through this.

Dennis Hensley: So you would literally fly from LA to New York to help him with this?

Dennis Osborne: All All the time. All the time. Yeah, all my time. 'cause he'd get stuck in puzzles. Well then he realized what you can do is you can, he would send me a copy of the game and send his code to what level he was at so that I could go through, play that level, fix it so that he'd pass it and then send it back to him so that he could go on to the next lever, lever after that.

So when he found out that you could do things like that online, that changed a lot too. It saved him a lot of money in airline fair. That's for sure.

Barry Joseph: Dennis, I have a surprise for you related to Oxyd, but before the surprise, I'm really curious to know, sitting with Steven Sondheim playing a puzzle game with him, trying to help him solve it, what did that teach you about Steven Sondheim, about his personality, about how his mind worked?

Dennis Osborne: What did it teach me about his personality? Um, he was a kid. You know, it felt like he was just a neighborhood kid, just that just somebody loved games, had an incredible sense of humor. He was incredibly generous. He would get very frustrated, you know, with games that he, when he couldn't figure something out, like any ambitious kid would, you know, he loved solving puzzles.

He loved solving problems and that was a big addiction for him. Big addiction. We would just sit for days on end. I mean, I used to go up when I was living in New York, I would go up there on Friday night and then we would play all night Friday, all day Saturday, all day into Sunday until the last bus back into New York.

Sometimes I'd have, sometimes we'd play through Sunday night and I'd have to catch the bus early to get back in, but we would just sit there and play Oxyd all weekend long.

Barry Joseph: Wow.

Dennis Osborne: And is

Barry Joseph: In connecticut, you're talking about place?

Dennis Osborne: Yeah, Rocksbury house.

There was a little room. We just called it the game room.

In fact, I said, you know, you realize when I die I'm gonna haunt this room. You know, I'm gonna, so if you see chairs and stuff moving around, just tell me to get the hell out. But I,

Barry Joseph: oh my gosh,

Dennis Osborne: spent so much of my, my life back then in that room, that little cubby hole of a room and the shelves all had games.

It was all video games, computer games. That's where the computer was in that room.

Barry Joseph: Amazing. Are you ready for your surprise? I am.

Dennis Hensley: Yeah. Yeah. Surprise.

Barry Joseph: So it needs a little bit of context. So just before you came on, Dennis O, I was talking with Dennis H about Steven Sondheim in Games Magazine. We were talking about his profile in January, 1983.

But what we had not talked about is that Steven Sondheim wasn't just in Games magazine. Games magazine was in Steven Sondheim's home. From 1977 when the first issue came out.

Dennis Osborne: Yeah.

Barry Joseph: Until he passed away, he looked at every single issue.

Dennis Osborne: Mm-hmm.

Barry Joseph: He curated every issue and he organized them on his shelf.

Dennis Osborne: Yeah, I know.

Barry Joseph: And all of those issues were sold an auction last year at the Doyle Auction, and a puzzle designer from Games Magazine named Andrew Parr, who lives in Canada, acquired them. And I helped out Andrew by picking them up for him, because I live in New York, and holding onto them just long enough to look through them all.

And what I was looking through in part was to see which were the games, puzzles and books that he circled. 'cause he was interested in them because as I'm sure you know, at the end of every year, Games magazine would do, it's like a hundred best.

Dennis Hensley: Yeah.

Barry Joseph: And so you would see games like The Fool's Errand and you can see what he circled.

Dennis Hensley: Mm-hmm.

Barry Joseph: And so when I heard, 'cause Dennis H told me we might be talking about Oxyd. I contacted Andrew and said, do you have Sondheim's issue? Do you have an issue that shows whether Oxyd was reviewed and if Sondheim circled it? So I have a video I'm gonna show with some good audio.

Dennis Osborne: Okay.

Barry Joseph: Now,

Dennis Hensley: oh my gosh, this is

really exciting.

Oh my gosh. Okay. Yes. I'm gonna allow it. Of course.

I'm gonna allow it.,

Barry Joseph: let me control the screen.

Dennis Hensley: While you're doing that, I just wanna con confirm with both of you guys, these computer games were immersive.

They would take days, right? It's not like, oh, let's do this for a couple of hours. Right?

Dennis Osborne: Oh yeah.

Dennis Hensley: Yeah. Different levels.

Dennis Osborne: It was at the beginning of them too.

Dennis Hensley: Yeah.

Dennis Osborne: And there wasn't any, there weren't any sheet sheets or, or websites to go to for answers. You were just on your own.

Dennis Hensley: Yeah.

Dennis Osborne: That's how he would fly me out there because he had no other alternative to get through these

games.

Dennis Hensley: Yeah.

Barry Joseph: And that's what we started seeing computer based games in the 1980s. Games that had stories and narratives and puzzles to solve and would take a long time to solve.

And often you needed a community of people or a book you could buy with hints and clues to get to the end, right?

Dennis Osborne: Yep.

Barry Joseph: What I'm showing you both right now is the beginning of the video. It's showing the cover of Games magazine from December, 1983, and the voice you're going to hear is Andrew Parr.

Okay.

Dennis Osborne: Okay.

Barry Joseph: This is so exciting.

Andrew Parr: December, 1993 Games magazine. Games 100. I started looking from the beginning and I didn't notice any marks in the entire magazine until we get to the games 100.

Barry Joseph: That's the game Set.

Andrew Parr: So he's knocked off, looks like one card game. Um,

Barry Joseph: The Seventh Guest,

Andrew Parr: he was interested in a few games and then maybe he got them and xed them off.

And the game you're looking for,

Barry Joseph: there it is. Uhhuh,

Andrew Parr: he circled it.

Barry Joseph: That's it. He circled it. And normally he circled it because what he was doing was saying, this is what I wanna get.

Dennis Hensley: Yeah.

Barry Joseph: And sometimes he would write the name next to the person who would get it for him. So that is telling us that most likely he learned about Oxyd from reading Games magazine when it came the December, 1993 issue.

And then that led to you Dennis O spending all these hours with him. And to be able to track that back, I think it's remarkable.

Dennis Hensley: That's amazing.

Dennis Osborne: Yeah.

The other funny thing is that The Seventh Guest was a game I recommended to him. Because I had got it first and was telling him about it and saying it was kind of Myst like, but with ghosts.

So he said he was gonna look into it and there he is. There's his little circle around The Seventh Guest . And that,

Barry Joseph: that's right. So you mentioned Myst. Can you tell us more about your relationship with Myst and Steven sondheim?

Dennis Osborne: Well, I got this excited phone call from him and said, I'm sending you a plane ticket. You've gotta get out here right away. There's this game, we're just going to, just gonna play it. I, it's, I'm not even gonna tell you what it is, justs, get on the plane and get out here. So I flew back there and we played Myst for five straight days without ever getting off the main island at all without

Barry Joseph: Oh, wow.

Dennis Osborne: Just going back and forth, listening to sounds 'cause again, no one had ever even heard of this game. I don't even know how he found out about it. Then finally the day before I was supposed to leave, we were very, getting very frustrated, just going through everything again.

And then we went into the little library and I, and we turned the map, the dial map, and all of a sudden I heard a sound that I thought, you know what? We didn't really listen to that sound or whatever it was, but this says tower rotation. Is there a tower around here somewhere? And sure enough, we went out, we saw that the tower at the top was in a different position, so we ran back in, found our way up there and there was the code.

It broke everything. And then I had to leave the next morning. So he was furious. So he sent me the game and said, put it on your computer. We're just gonna do this over the phone. So for days on end, we were just on the phone, on our speaker phones, trying things out at the same time, walking through Myst.

And we got through it. And then about maybe 10 months later, suddenly everybody was talking about Myst. and it just took off and it was all these, you know, op-ed pieces and, you know, and all over the place. And he called me and he said, what do you think about this? And I said, I, I know it's weird, isn't it?

Because it was so personal to just the two of us and nobody knew of it. And that game is so immersive that it makes you feel like you're really a part of it. And he said, yeah, I don't know. I don't think I like this at all. I don't think I, I like the fact that these people are walking around our island touching things.

Barry Joseph: That's great. Our island touching things. I love it.

Dennis Hensley: Did you enjoy the games as much as he did, or was it just, was a part of it you wanted to be a good friend to him and you did it? Or were you super into it as well?

Dennis Osborne: Oh God, no. I've always been into games, so I, it was one of the things that I think cemented our friendship so closely was we just shared that, you know, puzzle.

That's how I relax. I do all kinds of crossword puzzles and things like that. I've always done those.

Dennis Hensley: Yeah.

Dennis Osborne: So it was just this comradery that we had, when we met each other. That was just another thing that, that made us closer.

Dennis Hensley: Yeah. This is a question for you, Barry, but Dennis, you may have insight into this as well. You write about in the book, doing the interviews not long after he had passed. So a lot of the people that you talked to, even though you were talking about fun things like games and puzzles, there was a a, an emotional aspect to the interviews.

Yeah. Can you talk about that, what that was like? Um, there was a few places where I remember just reading it and being like, oh wow, that's really moving and really special.

Barry Joseph: Well, thank you. I appreciate hearing that it was moving for you. For me, there's places where I teared up writing it and there's places I still tear up reading it when I read certain sections in public.

There was a charge to the whole time, because as you said, I was talking to people six months after he passed away. So somewhere within the six month to 18th month period after he passed away, that's when I was asking people to tell me about their relationship with their friend. And I wasn't asking them to talk about what they thought about his music.

I was saying what was it like to play with him. And what they were doing was telling me about how much they loved being with someone. Just like you're talking about Dennis, like he was like a little kid. They got to see a side of him that most people don't get to see, and that's what they missed. So speaking with someone like Richard Malty Jr. who was just a few years younger than him and were very close friends, both in musical and in puzzle design, and he just said the thing that you, you missed the most about him was how funny he was. And that's what came to mind to him. So chatting with people in this period, it felt like I was like at a shiva where it wasn't the period, it wasn't the part of the shiva where everyone's crying.

It was the part where people were saying, ha ha, I remember that time when, and everyone laughs and they're laughing through the tears. And so I felt very lucky that people were letting me into their hearts during this time for them. And it was a big burden for me to carry those stories and try and figure out how to responsibly and respectfully and ethically share them into, and weave them into a larger narrative in the story so you can be part of understanding what it meant to have him as a friend.

Dennis Osborne: He was an astonishing friend. And we always say that if we, because we had a 30 year age difference and we were saying, my God, if we would've been the same age, the fun we could have had doing all of this stuff years ago.

And because it was hard for him to actually find friends that liked games the way he did. He didn't have that many.

Barry Joseph: Dennis can I ask you a question? Yeah. I asked this to people when I interviewed them towards the end of writing my book, because I kind of landed on something that was an insight.

It was what the material was telling me. I talked to over 120 people from my book, the large majority, 80 or 90 of them, knew Stephen Sondheim. And the picture that was emerging for me was this. And so I'm sharing this with you to say, does this ring true for you? And if not, how would you modify it? I write in the book that he loved games.

Designing them. Playing them. 'cause it helped him connect with people or create opportunities for people. He loved to connect with each other and he loved puzzles 'cause they were opportunities to create these moments of brilliant clarity. Like when, you know, order would form out of chaos, right?

Dennis Osborne: Mm-hmm.

Barry Joseph: And what I describe at the end of the book is that, okay, I said that's what he did, but not why. And what I describe is that Sondheim was so brilliant and his brilliance sometimes kept him separate from other people 'cause they couldn't understand who he was and how to connect with him. And while he wanted to connect with people and wanted to let them in, he needed to put up a barrier.

And that the games were the opportunity to connect with people. You're describing this beautiful story of these two friends connecting with each other.

Dennis Osborne: Mm-hmm.

Barry Joseph: But the puzzles would be the test, the puzzles would be a challenge. Not to say go away from me, but to say, if you wanna get close to me, you have to accept my challenge and conquer it.

And if you do, you will get the prize. And the prize is an entrance into my heart. And once you're in, you'll be there forever.

Dennis Osborne: Well he also had a lot of people in his heart that, that wouldn't know what a crossword puzzle even looked like. His heart was just so open. It was more than just games.

Games I don't think was the only avenue. I think because games were so special to him because they were about control and like you said, order out of chaos because he grew up in complete chaos and he loved that feeling of accomplishment. That was very important to him. But, there were many, many, I would say most of his friends weren't into games, not at nearly the level he was.

He had friends of all different stripes. I mean, there were a lot of friends that I would think, what the hell does he see in this person? But he, you know, he adored them and you would just sort of tolerate them, you know, if you had to be around them very much. And maybe they were saying same thing about me too, probably, but, um, it's, uh.

I think it's more than games.

Barry Joseph: Um, yes, absolutely. I don't mean to suggest that was his only way of finding connection with people.

Dennis Osborne: Oh, I see.

Barry Joseph: I'm just suggesting that that was one way for him to figure out how to let people into his life. One of many.

Dennis Osborne: Yeah. He,

he was impressed with people that could solve problems.

He was very impressed with that. I remember there were many times where we'd be sitting there, you know, and like there would even be visitors at the house and they'd come in and see us and go, my God, you're still at it. And turn around and, and, you know, walk away.

But the point was to solve, you know, to, to have the accomplishment like climbing Mount Everest or something. It was that these puzzles were what kept his brain going, which is why he lived as long as he did. 'Cause I, I swear I didn't think he'd make it to 60, you know, and 91 was incredible. Yeah, that's incredible. And he was still doing puzzles, you know?

Dennis Hensley: Wow.

Barry Joseph: In the book I interview Alexander Gemignani, the son of Paul Gemignani, and Dennis O, he says nearly the same thing, but in that context he's talking about the last treasure hunt he ever did, which we spoke about earlier in this episode, the 2013 City Center hunt.

Dennis Osborne: Yeah.

Barry Joseph: And Alexander's talking about the way he was creating these puzzles to think about designing not just a challenging moment, but a whole experience for people that would last an hour. That that's what was keeping him alive.

Dennis Osborne: Yeah.

Dennis Hensley: And he was in his eighties, right?

Dennis Osborne: 83

Barry Joseph: at that point.

Dennis Osborne: Wow.

Barry Joseph: Yep.

Dennis Osborne: Yeah. And but still, I mean, as sharp as tack. I mean I have video of him just a year before he died, walking around the kitchen, feeding the dogs, and you know, and doing all this stuff and you just look and think: this is not a 90-year-old person. This is, there's no way. This is a

90-year-old person.

You know,

Barry Joseph: a year before he died, mark Halpin, who was Steven Sondheim's favorite cryptic crossword constructor. Mark had sent him a crossword puzzle. Steven Sondheim had received it and it was a copy that was framed 'cause it was part of an award. And he wrote to Mark and said, can you please send me one in print?

'cause I actually wanted do it. Now Mark knew that Sondheim could do it just by looking at it on the wall,

Dennis Hensley: right?

Barry Joseph: But he was like, wow. He was still. At 90, 91, still doing crypto crosswords.

Dennis Osborne: And that's ninety years old, but that's 85 years of experience doing these things.

Dennis Hensley: Yeah.

Dennis Osborne: I mean, who has that kind of experience?

Dennis Hensley: Yeah.

Dennis Osborne: You know, that's all he lived for.

And you know, and although I think I would disagree with Mark, I don't think he could have done it in his head on the wall. He wasn't that adept at it. 'cause remember he used to fly me out quite a bit to help him get through, some of these puzzles and stuff. And then he probably just needed the company as well, you know?

Dennis Hensley: Yeah.

Dennis Osborne: If I think of it,

Dennis Hensley: it was a chance to be together

Dennis Osborne: and it could get very lonely out there in Roxbury before, you know, he was with Jeff, so,

Dennis Hensley: yeah.

Dennis Osborne: Steve wasn't super genius, you know, and he'd be the first one to admit that. He couldn't stand when people called him a genius because all he saw was failures in everything.

Dennis Hensley: Yeah.

Dennis Osborne: Like when we first became friends, when I first moved to New York, he invited me to the opening of Into the Woods, and he invited me as his guest and I was sitting up in the room where the desk was while he was changing. And I looked up at the corkboard and there were all of these reviews cut out and, and thumb tacked and they were curled up and you know, just sitting in all these different places. So I started to uncurl them and read them and they were all trashing him, every single one, saying he doesn't know what he's doing and who does he think he is, you know, every single review was a, was a scathing review.

So when he came out, I said, why do you keep these up on this bulletin board? And he said, because they're right. Wow.

Dennis Hensley: Wow.

Dennis Osborne: And after, And I, I remember taking that to heart thinking if he thinks that he's a hack, you know, what the hell are all these other people doing?

Dennis Hensley: Right.

Dennis Osborne: You know?

Dennis Hensley: Right.

Dennis Osborne: And that I really carried that with me through all the rest of my life.

Dennis Hensley: Yeah.

Dennis Osborne: Knowing that, yeah, you don't rest on your laurels. You don't wait for to be pat on the head.

Dennis Hensley: Yeah.

Dennis Osborne: Um, I know that's a little digression away from the games, but he's right, he wasn't what people were claiming he was, he wasn't super genius, you know, he just had a lot of experience and a lifetime experience and hanging around with incredibly brilliant people.

You can't help but pick that up and become not only one of them, but surpass them in so many ways too.

Barry Joseph: If we can go back to, Into The Woods for one moment and go back to games. Yeah. In the early nineties, Stephen Sondheim started exploring making an educational CD rom game connected to Into The Woods. I wonder if that, was it something that you had ever had an opportunity to discuss with him or if he ever brought it up?

Dennis Osborne: I don't remember that. No.

Barry Joseph: Okay. Thanks.

Dennis Hensley: Yeah. 'cause you write about that in the book. You mentioned his relationship with Jeff, his partner, and you talk about how the tone of the game nights kind of mellowed out once he

Barry Joseph: Yeah.

Dennis Hensley: Got into that relationship. Or maybe just getting older. Can you talk about how competitive he was and how that may have changed over time?

Barry Joseph: Sure.

Dennis Hensley: Barry and then Dennis, you can, you can chime in if you have thoughts about it.

Barry Joseph: Dennis O, lemme know what you think about this analysis. So, when you look at the games he was playing in the 1960s, just the titles, the names of the games were called Hostilities, the, the Murder Game, cutthroat Anagrams.

They were pretty challenging games emotionally, and they were really competitive. When you, I interviewed people who were playing these games with him in the nineties and the naughts and even the teens, the word that came up most often was generous.

Dennis Osborne: Mm-hmm.

Barry Joseph: As a player. As a designer. And that for me traced an arc in his life in broad strokes of looking at how the games he played and the games he designed reflected his change over his life from someone who had a lot of demons, who had processed a lot of them and was, now more generous with others.

Dennis Osborne: Oh, he was a generous, was is what was one of the foremost aspects of his personality. I mean, he was generous with everything. Everything. I mean, if he's gonna, you know, just send plane tickets out to people, I mean he, generosity was I think a major, major chord in everything, every aspect of his life.

Dennis Hensley: Yeah.

Dennis Osborne: So that doesn't surprise me at all.

Dennis Hensley: There's one person quoted in your book, Barry, who said that he has the youngest energy of anyone in the room. So when he's playing these games or leading these games, he has that child.

Dennis Osborne: Oh yeah.

Dennis Hensley: Childlike quality.

Dennis Osborne: It's funny 'cause I haven't had a chance to go back and look at the old videos, but I have a lot of old videos from that time and he is animated and hopping around and everybody else is just sort of trying to keep up with him and, but when he is telling a story and he's laughing and he's just, you know, so much energy.

He was very, very energetic. Even sitting down and talking, he'll be working one of those metal puzzles, you know, when he's in the middle of a conversation, when you're just chatting for the afternoon.

Barry Joseph: That's right.

Dennis Osborne: He just never stopped. Never ever stopped.

Barry Joseph: That was Jonathan Mark Sherman, the playwright who said that Dennis H and like you, Dennis O many decades his junior and yet was able to connect because as you just described, that youthful energy would come out.

Dennis Osborne: Yeah. He was ageless.

Dennis Hensley: Thank you for doing the Dennis H. Dennis H thing. You're nail, you're nailing that. You write about a few appearances that Steven Sondheim did on game shows, and you write about this password game and you write about this aura he had where he knew he was really good.

He knew he was competitive, but he was trying to act like it was just a delightful night. Like, do you know he was trying to underplay A, how good he was at this stuff, and B, how much he wanted to win or how well he wanted to do, which I just, it tickled me to know that he's trying to not seem as good as he is.

Right?

Barry Joseph: Yeah. He's the smartest guy in the room, but he's not acting like he knows it.

Dennis Hensley: Right.

Barry Joseph: He's not rubbing in anyone's face, but he is still gonna win. 'cause he's on this show with Lee Remick, who he loved and adored who had invited him on to be, you know, so someone goes on the show and then they get to bring their friends, like, I think Lee Renick's mother maybe was on before Steven Heim.

So it's Steven Sondheim's turn to help Lee. And she's gonna, he's gonna do everything he can and if anyone gets in his way, he's not gonna be happy. And one of the things I love about this moment, this was, uh, Christmas, December 25th, 1966. He starts asking the question, but through some technicality, the host stops him.

And once the host stops him, he just deflates. He's like, who the hell are you? He doesn't say anything like that, but you can see it in his face.

Dennis Hensley: Right.

Barry Joseph: His entire body language changes. And then the host explains what the rule was that he broke one that was never really explained and says, go on again. And Sondheim doesn't start. He's like, are you serious? You want me to do it again? And then the host says, go on, do it again. And then, so Sondheim kind of like disgruntled starts again, but before long, they're in such a groove. Him and Lee Remic and they solve it and they solve it beautifully.

And then they're laughing again and they're looking at each other and watching the two of them connect through gameplay live in the television show is amazing. And you can, anyone can watch it. It's all on YouTube. Just look for password, Stephen Sondheim, and you can watch the entire appearance. It's remarkable.

Dennis Hensley: I love to see that.

Dennis Osborne: He was also, he was also very humble.

Dennis Hensley: Yeah,

Dennis Osborne: He was extremely humble too. Yeah. Which is very disconcerting because you think that there's gonna be all this, you know, grandiosity and, I mean, I guess it's a little bit different. I mean, because when we became friends, he hadn't reached iconic status yet.

You know, this was, you know, pre Into The Woods, so.

Dennis Hensley: Right.

Dennis Osborne: It was just starting and I, and I saw a big difference, but he always stayed humble.

Dennis Hensley: You met him at a time when you were only as good as your last hit. Right? As opposed to now there's that body of work and he's iconic.

Clearly.

Dennis Osborne: Yeah.

Dennis Hensley: Yeah.

Dennis Osborne: And he had suffered just a couple years before that he had suffered through the failure of Merrily We Roll Along, and then the critical triumph of Sunday in the Park with George had just happened. In fact, I think he just won the Pulitzer right when we met. But it was also, he was losing a lot of friends from AIDS at that time.

It was a very dark period. The thing that always astounded me was how instantly comfortable you feel around him and how genuine... he's one of those people that when he asks you a question, he listens and is not waiting for the next thing to say. Which makes him so smart, you know.

Dennis Hensley: Oh, and he's,

Dennis Osborne: but, um,

Dennis Hensley: known for being a good mentor to other writers and to probably people like you.

Dennis Osborne: Well, yeah, he was my mentor for 35 years.

Dennis Hensley: Yeah. Yeah.

Barry Joseph: Wow.

Dennis Osborne: And, because again, he wanted to be a teacher, but yet he waited also until he found the right people that he could invest that in. So that's why he didn't go to colleges, you know, to teach colleges and stuff like that.

He would find us through other friends and see if we had a kind of a mind that he liked. And then go from there. And if we did, especially with puzzles, then... I would never have the life I have now if it wasn't for him. I owe him everything.

Dennis Hensley: Oh, that's beautiful. Um, Dennis is a huge fan of The Last of Sheila, the movie.

And Barry, you write about that in the book. They did like puzzle promotional things.

Barry Joseph: I got from last of Sheila this summer the press book. The press book is the thing that you would get like if you were in media, right?

That would tell you this is, you know, some copy you can put in your review. Here's some photographs you can use. The other thing in that broad sheet is an original Al Hirschfeld. It is the cast of the last of Sheila.

Dennis Osborne: And he had that Hirschfield in his writing room at the Roxbury house. The original.

Barry Joseph: That's how much it meant to him.

Dennis Osborne: Well, that's actually how we became friends because I saw that movie when I was a kid 50 times.

It was playing at the neighborhood place I would go to so I could avoid going home. And so I just would watch whatever movie was there for the whole week it would be there, sometimes twice a day, every day. And that one came in. I remember thinking the Last of Sheila, this sounded like a romantic movie or something, but I thought, I'll see it anyway.

And it blew me away. And it was the first time at the credits. At the beginning it said written by Tony Perkins and Steve Sondheim, and I thought this was written by somebody when I saw it. The second time I thought this, somebody wrote this and it made me want to write, and that was when I was a kid.

So years later when my friend Tom Fitzsimons had introduced us through a letter, I got a letter from him and said, you know, Tom tells me you're a writer and blah, blah, on and on. If you're ever interested, you know, you need some advice, let me know. So I wrote him a letter back and it was all about The Last of Sheila.

I mean, because that movie had meant so much to me as a kid. And puzzles again just changed my life. And that's what started our correspondence because he said, I can't believe you have picked things outta that movie that no one has ever been able to figure out. And well, you can't watch a movie a hundred times and not, you know, get everything from it.

But that's how we struck up that friendship. And then he suggested I move to New York, and he would get me involved in the ASCAP workshop and things like that, which he did.

Barry Joseph: That's amazing.

Dennis Osborne: That's how we became lifelong friends. The last of Sheila I have to thank to that. There you go.

Barry Joseph: The Last of Sheila became the first of your relationship with Sondheim.

Dennis Hensley: Dennis, I just wanna ask you, what was it like to think about your friend and, and this part of his life?

Dennis Osborne: It was just so much of his life. I mean, it was his life. I can't disassociate the two: games and Steve.

When I think of Steve, I think of games. More even so than the musicals because when we met, I wasn't all that familiar with his shows. I had never even heard, you know, half of them. But I just knew that he was brilliant and I know he was great, but the games was a whole big surprise to me and that's what really bonded... the game and the writing.

Dennis Hensley: Yeah.

Dennis Osborne: And in fact, I was just going to show you, I just found this a month ago,

Dennis Hensley: More surprises.

Dennis Osborne: Sometimes I would just get things in the mail, it'd be a box, and there was a little envelope in it and I opened it and it's all these little puzzle pieces. And so I did the puzzle, but then when you turn it over, every puzzle piece had a letter from his name on it. I realized I could have just put the puzzle together that way instead of, sure.

It would've been much easier, but I put

Dennis Hensley: You did it upside down. Yeah.

Dennis Osborne: Well, no, because everybody does puzzles by the picture.

Barry Joseph: Yeah.

Dennis Osborne: But he would do little twists like that. And just send 'em off in the mail. And for his 88th birthday, I made a little mystery puzzle box that you had to unlock and I sent it to him and he could not open it for..., he couldn't figure it out at all.

Dennis Hensley: You had to fly out?

Dennis Osborne: No, I didn't have to fly, but he kept calling me, give me another clue. Gimme me another clue. I'd say the, the numbers. 'cause there was a code of numbers you had to put in.

Barry Joseph: Yeah,

Dennis Osborne: they're right there in the inscription. They're right in front of your face.

Barry Joseph: Yeah.

Dennis Osborne: So he'd looked at it and I'd say, read me the inscription.

So he'd read the inscription and I'd say, you didn't hear that? Oh. Oh, okay. I think I did hear it. And then he'd hang up. Then a week later, I can't, I can't get it. I don't know, I can't, I dunno what it is, but look at the inscription. It's right there. And he couldn't do it for the longest time. And he finally did by me sort of nudging him enough.

Yeah. You know, closer to it. Yeah. But he obsessed on it and obsessed on it and obsessed on it because he was going to figure it out without taking a hammer to it and opening it that way because there were coins in it. There was a quarter, a dime, a nickel, and a penny all from 1930 in it.

Dennis Hensley: Wow.

Barry Joseph: Nice.

Dennis Osborne: So, but then he got back at me 'cause he, when he opened it, he called and he said, just wanna say, I, I got it. You know, everything's fine. And it was, it was great that what you had in there because my, um. My housekeeper was here and she bought some supplies and she needed some change for the dollar and thank it was just the amount that you had put in there.

So it was, you know, the quarter and the dime. So I gave it to her and I went, Noooooooo! I mean, he knew he was, you know, he knew he had not done that. Yeah. But he made me think that he just gave that change away

Dennis Hensley: that he didn't notice.

That's so wild.

Dennis Osborne: So, He just started laughing. It doesn't surprise me that Barry wrote a book about his games.

I mean, I always thought somebody would at some point.

Dennis Hensley: Yeah.

Dennis Osborne: Because it was so much of who he was.

Barry Joseph: Well, can I ask you, as someone who has known him for so long and experienced him as both a creative mentor and a puzzle game playmate, people have said to me, why didn't this book come out earlier?

Do you have a sense of why we didn't see this in the nineties, or the naughts or the teens?

Dennis Osborne: you just weren't ready to write it yet?

Dennis Hensley: It was waiting for you. You were the person to do it.

Dennis Osborne: It was it was meant for you to write. I mean, it's a

Barry Joseph: Aw shucks.

Dennis Osborne: Yeah, no, I'm serious. It's a, you were the one to come along and do it.

I think a majority of his friends just would roll their eyes when they would talk about his games. You know, they just,

Dennis Hensley: they didn't get it.

Dennis Osborne: Oh. His little fascination, you know?

Dennis Hensley: Yeah,

yeah.

Dennis Osborne: There was handful of people that were into it as much as he was.

When I first met him in person, he had left me a ticket to see Sunday in the Park with George.

Um, and it was, I think the last night, and I had just flown into New York that day. I went and saw it. I loved it. Of course. But I didn't call him for two weeks because I thought, oh, he's not gonna want to be bothered with me. But after two weeks in New York, I was so lonely that I called him and he was panicked 'cause he thought I hated the show.

I never wanted to see him, I never wanted to meet with him. And I just didn't know what to say, you know, and all that other stuff. So I said, no, no, I just thought you'd be too busy. And I said, no, I've been waiting for you. I, I called the box office. You picked up the ticket. I didn't know how to reach you. I don't, you know, I was just panicking.

Why don't you come over? What are you doing right now? And I said, well, nothing. He said, come over, we'll have a drink and we'll talk about it. So I thought, oh God, okay, here it comes. So I went in, we sat down and we got in the biggest fight about Sunday in the Park with George because I was talking about how amazing it was.

And then I said, but you know, I think I would have started with the second act and then out of frustration of what he was going through that's how he learns his lesson through his grandfather. You know, a thread like that. I thought that might work a little bit more the thematically for me, and he poo-pooed it.

And I was trying to explain to him, no, but I, but I think it would be great because like the song Sunday should be the finale of the show because you never recover from that. And so the whole second act, you're just trying to get up to that moment again. You never quite do. If they were reversed, it just seemed to me- I was going on and on and he kept fighting.

And then I finally thought, what the hell am I doing? Shut up. Yeah.

Dennis Hensley: There's a Pulitzer over there.

Dennis Osborne: Who do I think I'm, I'm some stupid idiot from Garden Grove. Right. You know? So I just sat there, you know, I just shut up and was listening to him. And he kept going and kept going and kept going. Finally wind down.

And he said, what's the matter? Why'd you stop talking? I said, I just, I realized what an idiot I must sound like. And he went, oh my God, don't you know how hard it is to find somebody with an opinion?

Dennis Hensley: That's interesting.

Dennis Osborne: He said, that's why he said, you're right. That would have worked brilliantly. We never even thought of that.

It never occurred to us. Yeah. To do that, that would've been brilliant. And you're right, that sound, that moment is the moment of the show. You're right. I, we never thought of it. Never, it never crossed our minds. That's why I'm arguing with you, because I'm trying to get around it. I'm trying to get out of it, but it's there.

It's, you know, so I don't think he faced a lot of criticism from a lot of people.

Dennis Hensley: Right. Right.

Dennis Osborne: So, games and that moment, when I was sticking up for my point, that really impressed him and he probably thought,

Dennis Hensley: this guy's a keeper. Yeah.

Barry Joseph: This, yeah.

Dennis Osborne: And all through these thirty-five years, whenever he was working on anything or offered anything, he'd send it to me and want my opinion, because he knew that I would be honest with him and I wouldn't lie to him.

And very few people would do that.

Oh God. Here comes another anecdote. I guess if I'm saying too much, just tell me. No,

Dennis Hensley: it's okay. It's okay. I have another podcast at four, but we're okay.

Dennis Osborne: Another aspect of how interesting that man is. They were doing The Doctor is Out and it was being done in San Diego and they were working on it and Steve left very happy because it was all look all in great order.

Everybody was saying how brilliant it was, and it was gonna just go right to Broadway and all this other stuff. So they were already lining up investors. Well, he got home and the reviews were scathing. So he called me and he said, I want you to go down there and I want you to watch it and tell me what, what's wrong with it.

So I did. It was terrible. I came back and I told him all these problems. He hung up on me. Then he called five minutes later, "Pick me up at the airport at five o'clock. I'm coming in there, we're going to go down and watch it together, and you're gonna defend everything you said." All right, bring it. So I picked him up from the airport.

We drove down there. Five minutes into it, he dug his hand into my thigh and just kept going: Oh my God, I'm so sorry. Oh, I'm so sorry. How could I have doubted you? God. Oh my God, it's horrible. It's terrible. Oh my God. And so afterwards we went out to, we drove to this, we stopped at a coffee shop in the middle of Oceanside with nobody around except a family, you know, a husband and wife and about three kids sitting at a one table.

It was just some motel. And he was just panicking because it was gonna go to Broadway and he knew he was gonna get blamed for everything and he really didn't have that much to do with it. But I said, I think the problem was that you kept seeing the improvements and when you left, everybody was saying how good it was that you were, comfortable that it was gonna be fine, but now you've had distance and seen it, know what it is.

And then in the middle of that conversation, the father from that table, in the middle of Oceanside, in the middle of nowhere, walked over to our table and he said: excuse me, are you Steven Sondheim? And Steve looked up at him, you know, through his tears and: yeah.

And he said, I can, I just tell you how much your work has meant to my family, and I? I just want to thank you. I don't wanna interrupt you, but, but just keep doing that. You meant so much to us. And it completely turned him around. Just this, this stranger.

Dennis Hensley: Oh, that's beautiful.

Dennis Osborne: can I, It did go to Broadway, and bomb, and he did get blamed for it.

So

Dennis Hensley: there you go.

Barry Joseph: Dennis O, I have a question for you, and I don't know if you have an answer. I have heard that in connection with the show, the play, you're talking about getting away with murder, that there was a murder mystery party designed called murder in room 1213. I have learned nothing else except for what I just told you.

Were you aware of anything like that at the time?

Dennis Osborne: I'm not.

I know that he was doing a lot of those things when I moved from New York. He would call me with updates about these parties and stuff. I'd always wanted to go to one, but I was never able to make it out for one. So it just may have been one of those ones that he was planning.

Barry Joseph: I heard it was a murder mystery party where one of the guests has killed their psychiatrist, which of course is similar to the plot.

Dennis Osborne: That's the play. Yeah.

Barry Joseph: Yeah, exactly. Uh,

Dennis Hensley: I have a couple more questions for Barry before we wrap it up. I was looking at your website. You do a lot of different things and and I can connect with that.

And I'm like, you are a hustler.

Barry Joseph: Just like you Dennis H.

Dennis Hensley: I'm

like, you're a hustler.

I'm like, this guy's a hustler. What, what motivates you? What keeps you going and drives you and gets you excited?

Barry Joseph: I love that. You're asking what motivates me. And I looked at your material and I thought, how do you decide what to say yes to?

I love all. No, but nobody, nobody's asking.

Dennis Hensley: I have to pick. I have to pick it. Like, you know what I'm saying? It not like happen. Yeah. Yeah. And that's okay.

Barry Joseph: So I look for the things that motivate me. That make me excited.

Dennis Hensley: Yeah.

Barry Joseph: That'll gimme opportunities to pursue passions.

Dennis Hensley: Yeah.

Barry Joseph: To work with the people who are grounded in connecting with people and not just kinda lost in their processes.

Dennis H, I never met you before and I've had so much fun

Dennis Hensley: Aw.

Barry Joseph: Spending time with you on the podcast.

I love that

you, Dennis O, Dennis H brought you into my life now.

Dennis Hensley: Yeah.

Barry Joseph: I love to do things like this. So yeah. Doing a project, like writing this book forced me to meet scores of people, many who are now my friends.

Dennis Hensley: Yeah.

Barry Joseph: I wake up this morning and someone says, Hey, I know you're doing this thing for the book on Thursday. How's it going? And I didn't know them before this project. So I love to pick things that are gonna connect me with other people

Dennis Hensley: Yeah.

Barry Joseph: Who have similar values, who are gonna help ground me in my life.

Dennis Hensley: Yep.

Barry Joseph: And help me pursue my passions and develop them

Dennis Hensley: that's why I do this podcast,

Barry Joseph: And help me remember who I am, who I wanna be.

Dennis Hensley: Yeah. Oh, wow. I relate to that a lot. I have one more question for you, Barry, but tell people how they can find the book, any events you've got coming up, anything you want to let people know about.

Barry Joseph: Oh, it's the time to sell everything. Okay. So buy my book. It's available where all fine books are sold. Right. Please go to your local independent bookseller. If you have to, of course, go to Amazon and leave a review. But the book is only one piece of the project.

Dennis Hensley: Yeah.

Barry Joseph: I also have my podcast.

I also have an exhibit at the Drama Bookshop. I also do workshops. I'm traveling all around the country.

I'm hoping to go to London as well when the book comes out there in December where I teach people how to design Sondheim- style parlor games. And we get to play the games he designed, like the murder game. And I love to bring up special guests, the people who I've learned and got to know over the course of this amazing journey for the book. And bring them to the audiences as well so they can experience them and build their own relationships with those amazing people.

People like Dennis O who I'm, meeting today's the first time.

Dennis Hensley: We have to get you out here to LA and do one out here. We have to make that happen. I get it.

Barry Joseph: Someone says that to me every two days.

Dennis Hensley: Nobody ever delivers. All right. All right.

Barry Joseph: Let's do it. It's gonna happen, Dennis. It's gonna happen.

Dennis Hensley: Dennis, we have to figure that out because I would love to do one of those treasure hunts.

Dennis Osborne: Or the murder game. Just even play the game. Yeah.

Barry Joseph: Who says or? Why do you have to choose?

Dennis Hensley: Exactly. Do it all.

Dennis Osborne: .Oh, yeah. I, I would love that. Yeah. That I would love.

Dennis Hensley: And Barry, your Instagram is great too. Um, I have one more question for Barry, but Dennis, any other thoughts you have on this topic or, or what this experience has been like or anything you wanna share before we wrap it up?

Dennis Osborne: I'm just thrilled to meet Barry and thrilled that he wrote this book because it was such a part of my life and I can't wait to finish it. It's just such a great book. And I do have a picture of Steve playing Oxyd that I'm gonna send you.

Barry Joseph: Um, wow.

Dennis Osborne: The

Dennis Hensley: Barry's face was like, oh my gosh. Yeah.

Dennis Osborne: On his little laptop over his shoulder. He was playing Oxyd. Yeah. Um, and I just thought, yeah. So I, I have kept that for a long time.

Barry Joseph: And with your permission, Dennis, oh, I'll put that on the Instagram feed, which is @matchingmindswithSondheim, where I post all the amazing things that people send me.

And, um, that's where I, I'm the best place to connect with as well, if you wanna talk with me online.

Dennis Hensley: I love it. Here's my final question for you, Barry. Reading this book made me love Steven Sondheim more. I just, it, it gave me a new dimension to him. I made, I felt a connection to him because I like some of these same things.

How did working on it change you?

Barry Joseph: Working on this book in short helped me understand myself in a new way.

Dennis Hensley: Mm.

Barry Joseph: It helped me understand how my mind works. How I try and create and design experiences for others that are both for them, but also for me as the one who's creating them.

Dennis Hensley: Right.

Barry Joseph: And it got me to appreciate when Sondheim was doing it, what values he was trying to bring out into the world through what he was creating. And to help me remember to keep those in mind for myself as well. The three most important ones being generosity, playfulness, and mentorship.

Dennis Hensley: Beautiful. What a lovely note to end on.

Dennis Osborne: I can, I can make a little point about that book too is I've not really talked a lot about Steve in my life. I've usually just kept that, you know, private. But this book has made me think about him and sort of brought him back to life again.

That's why, you know what I found that little puzzle thing again and when Dennis asked me to do this, I thought, yeah, I think I am ready to- 'cause like, you know, when Meryle Secrest did the book and people asked all the time, I never talked to anybody. But this-- talking about games and Steve's game-- I thought this might be fun.

This might be a time to start talking about him again.

Dennis Hensley: Yeah.

Dennis Osborne: You know, after so long. So I'm grateful for that too. 'cause it's and he's back.

Dennis Hensley: When you show that little envelope with the things, they are acts of love, creating these puzzles. They are acts of love.

Dennis Osborne: Oh yeah.

Dennis Hensley: And that comes through the, in the detail and the intricacy.

He did that 'cause he loves you, you know?

Dennis Osborne: Yeah.

Dennis Hensley: It's beautiful. All right. I was like, I, this is an hour and a half and I haven't cried yet. What's going on with this podcast, but I kind of did. You guys, thank you so much. This has been a real treat. I really appreciate it. Thank you.

Dennis Osborne: Thank you very much.

Barry Joseph: Both Dennis's, thank you so much.

Dennis Osborne: Thank you, Barry. Very great to meet you.

Barry Joseph: Yes, absolutely. It was such a pleasure.

George Lee Andrews: We were there.

Marty Morris Lee: Oh, it's so much fun.

Etai Benson: There's no better way to represent his brilliance than through puzzles.

Colm Molloy: I feel like he was probably more obsessed with puzzles than musicals. Maybe that's heresy.

Will Shortz: He was a brilliant puzzle solver. and a great mind.

George Lee Andrews: It was quite amazing when you walked Into his apartment because it was full of games and puzzles.

Michael Mitnick: When Sondheim started to build the cryptic crosswords for New York Magazine,

Stephen Rodosh: his treasure hunts were legendary.

George Lee Andrews: Everybody was just running around screaming and laughing and having

Erin Ortman: it's almost ridiculous to be like, yeah, I went on a. Scavenger Hunt created by Stephen Sondheim.

Michael Counts: You know, in some ways you could almost consider him like the sort of inventor of the, very form of escape rooms because he

Taylor Myers: Stephen Sondheim blurted out when the final exit door opened, but I wanna stay.

Marty Morris Lee: How cool that we're sitting here trying to figure this game out.

Again,

Richard Maltby, Jr.: I, have to say, I'm so grateful to be invited to, participate in this. I can't tell you. It's just such a gift. You know, and he's here, you know, he's here.

Ann Morrison: Matching minds with Sondheim. Tell a friend and quiz him. Test him on his anagram. He's pure hedonism. His songs and his shows. Mary Flynn, Mama Rose. Everybody already knows they're superbly designed. But where would we be without a puzzle to bring us glee. Even someone in a tree would believe we need Steve and his mind.

Dennis Hensley: Beautiful. What a lovely note to end on.