The Dan Le Batard Show with Stugotz - South Beach Sessions - Jon Cryer

Episode Date: August 28, 2025

"You're always sure that another shoe's gonna drop and this is all gonna go away..."  A teenage icon turned struggling actor to Emmy Award-winning sitcom star, Jon Cryer has seen every side of Hollywood and made an impact most couldn't even dream of. Jon tells Dan what it was like growing up in a showbiz family and how he experienced fame early in his career with "Pretty in Pink", being associated with the Brat Pack, and performing on Broadway as a teenager. He also explains the unique disappointment that comes with working on a failing TV show or a movie that bombs... to the then life-altering popularity of "Two and a Half Men", how he's moved on since it ended, and why he's still not ready to reconnect with Charlie Sheen. Listen to the true crime podcast, "The Man Who Calculated Death", available on the Wondery app or wherever you get your podcasts. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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amex.ca slash yamex this episode is brought to you by defender with a towing capacity of 3,500 kilograms and a weighting depth of 900 millimeters the defender 110 pushes what's possible learn more or at landrover.ca. child prodigy, practically born on off-Broadway, right? Born off-Broadway? Now that you mention it, yes. I've rarely been referred to as a prodigy. I tend to think of like Mozart. That's my level of prodigy. I'm not quite at Mozart, just yet. Fair enough. But knew you were going to be. On my way. John Pryor is what I should have said. I'm sorry. I haven't actually said your name. There we go. Because you objected immediately the prodigy.

But you were going to be an actor from the very beginning. Yes. You had no choice. I had no choice. Yeah, no. My parents were performers. My mother's also a writer and composer. And so I grew up kind of backstage and in it.

You know, I actually had a weird thing recently. You're a paid professional. I'm going to put the microphone in front of you. Don't make love to the microphone. Okay. Okay. So I recently had an odd. situation where a friend of mine recommended a memoir of a, it's kind of an avant-garde producer

from the 60s, 70s, 80s, a guy named Albert Poland. It's called Stages is the memoir. And he said, you've got to read this because your parents are all over it. I was like, I'm sorry? And it turns out my parents obviously being very active in off-Broadway and some amount of avant-garde stuff at the time. It is so strange to read a memoir that deals with your parents. as people, you know, because you don't picture them that way. You know, so it's, it's revealing all these things that I had not, you know, had not expected. What'd you learn? Well, the biggest thing I learned was, like, my parents were divorced when I was four. My dad is David Cryer. He's, he's an actor, been on Broadway and off Broadway, ended up doing Phantom of the Opera on tour for 19 years.

Well, no, 17 years on tour and then two years more on Broadway. So, I mean, that's, that's, that's, how ingrained it is. You had no chance. I had no choice. But I always wondered, it's like I have no recollection of him before my parents divorced, almost none. I have a couple of incidents that I remember. And in reading the book, I now understand why. It's because he had, as a producer and a star, embarked on a huge tour that he, that on and off,

he was on for approximately four years. And that's why I didn't see him, you know. And obviously, you know, we've gotten to know each other over the years, but that was an, but it was interesting to read this book and suddenly go, oh, there's this big chunk of my life that now makes a lot more sense. What a fascinating read that must have been. How much learning? I'm not done. I'm only a third of it the way through. I'm already going, Jesus Christ. So it's wild, but it's been fun. What else did you learn? Mostly, well, that my mom, my mom is a Gretchen Cryer. She's, as I said, a writer, a playwright and a composer and an actress.

And she had, and he, the author characterizes her as pessimistic but funny, which was never my experience of my mother. My mother was always just unfailingly optimistic. That was just a part of who she was. and to hear that somebody perceived her completely the opposite was remarkable to me. And I got to have a talk with her about that. I was like, what was going down when you were hanging with Albert? I don't know. You mentioned incidents.

Before four years old, you have something ingrain there. Sure. I mean, there's a few things. You know, there's a time when I remember, I've been. him as a joke, I'm using air quotes, and that it was one of like my first sort of pranks as a human being. And I thought it was hilarious, and he did not. So that's a moment that I recall.

But by the way, just in the future, as a prank, it's not a great one. It's not a great one. No, through a child's eyes, though, where I would, I can understand. I could understand the confusion there. But you are, so you were a child actor from what age? How early were you on a stage? Well, my very first job was I was four years old and was in a commercial for multivitamins called Zestabs. They were basically once Flintstone vitamin, they were basically the antecedent to Flintstones.

And once they realized with zest tabs that vitamins packed with sugar were very successful in the marketplace, then they came out with Flintstones and all the, then they specifically branded it toward children. You interrupted my introduction of you to say you weren't Mozart. And at four years old, you were out here selling zest tabs, poisoning the children with sugar. with their poisoning America's children. You know, again, I didn't say that I did it well, which I think what you need to be a prodigy. No, in fact, on the day of the commercial shoot, apparently, I broke out in hives that were incredibly visible. And literally, the production had to just wait for like four hours until my skin cleared. That's the opposite of Mozart.

Exactly. You were right to correct my introduction, actually. You're welcome. Did you actually, are you being self-deprecating or were there actual hives? There were 100% actual hives. So you were nervous? I was very nervous. I was very nervous.

How much pressure was there in the house? None really. All I had to do was stand there. I didn't even have a line. Basically, my mother had booked the commercial. She was an actress and it was a great gig. And they needed, she needed to be, the whole theme of the Zest Tabs commercial was. And the kids like them too.

because they're packed with sugar and so she just needed a boy and a girl to be standing next to her and I and she asked my sister and I and my sister ran screaming from the room wanted nothing to do with show business and but I was like yeah let's do this because it sounded interesting

to me and and but of course my nerves overtook me on the day the crazy thing was the girl who was with me in the thing was named Jennifer and many, many years later, we were sitting at a play, we were going to see the little foxes that Elizabeth Taylor was in, and the mom recognizes my mom and says, oh, here's Jennifer. And we were both grown people at that point, but it was lovely to see her again. Teenage icon more acceptable to you?

Yes, okay, I'm an icon. You've talked me into it. What was the life like between? four and pretty in pink? Not much happened. No, between four, you know, I didn't really try to work, obviously, after that, but I was always fascinated with TV. I loved TV.

Absolutely. Just my, it was the bane of my mother's existence that I was just glued to it. I had a little Sony TV that was way, the screen was about three inches by two and a half inches, no, maybe four inches by two and a half inches, black and white. But of course, the thing was probably 12 or 13 pounds. What were you consuming? You were just addicted to it? I was addicted to mostly sitcoms, loved them, love sitcoms, loved, you know, all the mash and, you know, and Merritteller Moore and Rhoda and good times and all in the family, all that stuff. And I remember though, I remember the moment that I thought that my, my horizons experience.

expanded quite a bit was I was watching Kerbernet show, which I believe was on Saturday nights, I believe, or was it Sundays? I don't know. And then there was the news. And then there was this weird show that I couldn't tell what the hell they were doing because I didn't know, like there was this guy doing a weird voice and he sounded like he was foreign, but you couldn't quite understand him. And then he would play the Mighty Mouse theme and lip sync along to it. And it was hilarious. And I was like, Who is this guy? And it turns out the show was Saturday Night Live. You know, and so it was, it was, I remember that moment that comedy kind of changed.

And it was really, it was remarkable. You happen to be watching at the moment that it changed. Yes. Where live television is, comedy is coming to live television. What level of awareness and gratitude did you have whilst? starring for 10 years on America's number one television show that you were now the thing that was in that box in your childhood that you were obsessing over,

that you were right in the center of its golden age? Yeah, it didn't, it didn't occur to me like that because I was too suspicious by that point. I was not, you're always sure that another shoe is going to drop and this is all going to go away. It's very, and in the end, and it's funny because about eight seasons in, A certain co-star went a little bonkers. So, you know, it's a hell of a run, though.

It was a hell of a run. And no, I did. I knew how lucky I was. It doesn't sound like it, though. It sounds like you're saying. There's always a part of you as an actor that's like this can end at any moment, because it can. But when CBS bought two and a half men and they ordered 13 episodes, which is the normal amount. And then when they gave us the time slot after everybody loves Raymond, which at the time was sort of at the height of its popularity.

And once they did that, I said, oh, okay, I think, you know, I think this thing is going to is going to take on. Are you sure? Are you lying to me about, like, sometimes very often success doesn't feel like success to the successful because they always crave more. They want more. They think it's going to, they think it's going to fail soon. They don't get to enjoy it while they're doing it because they're competitive or whatever the reasons are. No, I absolutely enjoyed it while I did it. And situation comedies are like in front of an audience, multi-camera comedies, are the best job you can ever have. They're amazing because, you know, the hours are normal. They're predictable.

If you want to have a family, you can have a family. You have copious amounts of time off. I mean, we would shoot three weeks and then take a week off every month. And then we had all of the summer off. So, you know, for actors, they're very sought after jobs because of that. Also, it's just really fun working with the writers and, you know, you get a lot of rewrites. That's the hardest part of it.

But, again, it's incredibly fun because they're figuring out what you can do well and you're giving them the best that you can. So, no, I felt very, no, I knew that it was a great situation. And I loved that. And I didn't feel, it was interesting because working with you. Charlie Sheen, you know, he's obviously, you know, he was already a huge star at that point. And, and I found he could be, I remember like the first couple of seasons we didn't get any Emmy nominations and, and he would just, you know, quietly seethe about it. I mean,

it was, it was sort of jokey. He turned to me at one point. He said, it's all about exclusion and inclusion. And I was like, okay, if that's what it's about. I think he just wanted to be invited to the party, you know? But, But I found that, you know, that it, one of the things that, you know, having been in this business since I was four, you do realize that you can make yourself incredibly miserable if that's the way you choose to live your life, you know, but you can choose that and you can just as easily choose not to. Where'd you learn that? I suspect from watching my parents. My parents very early on had been through, you know, had been through tough stuff. And I remember my mother, she was a playwright and she'd written shows that were,

she'd written several off-Broadway shows. And, you know, you never know how they're going to be received by the New York critics. You know, the New York Times is like the big one. Like, you know, it's, you know, a lot of artists in New York just hate the New York Times because of the power they wield. It's not necessarily that they're, you know, awful or they, you know, their reviews are not quality or whatever. But I remember my mom had had a couple of hits off Broadway. And then she did this incredibly autobiographical show called I'm getting my act together and taking it on the road. And she'd worked so hard on it for years, and it was this part of her.

It was, you know, as I said, it was very much about her life. And it opened at the public theater and got one of the worst reviews in the New York Times that I had read. I mean, and I remember just my mom just being decimated by it, just absolutely decimated. And but she was decimated for a day. And then she got up and went back to work. And the show ended up running for six weeks. Joe Papp, who ran the public theater at that time, decided to give it another few weeks. And by the end of that extra four weeks, it was selling out.

It ended up moving to off-Broadway and running for three years and was the most successful thing my mother did. And, you know, that was a huge lesson for me because I got to see that, you know, that even in something you perceive as just an utter defeat, there's always a little something that could, that can turn these things around. How old were you? And what do you remember of the details of the decimation? I was 13. And I, well, you have 78. So yeah, 13. It's pretty crushing to have to put something that personal into the world. If you're an artist and just leave yourself splayed open vulnerably for the critic and then have your worst nightmare read that whatever she was reading yeah it's awful i mean people in the theater are always like you know screw them and you know we always

you know they're always put on a brave face because it's always the theater is always kind of a silly it's it's it's a ridiculous thing we're pretending we're grownups pretending things we get that you know so on some level we understand this is all ridiculous folly to begin with uh but uh uh uh But again, as you said, it was an incredibly personal thing for her. So, yeah, I remember her in her bedroom with the, you know, the blinds drawn and just crying, just crying it out, you know. And that was one of the first times I recall really understanding my mom's vulnerability. You know, when you understand a parent's vulnerability, it's very different. So you'd never seen that from her or?

No, no. Not that, you know, she never cried or anything. but but just just that the the bridge the link being that clear to a 13 year old between mom cares about this thing and also I was 13 so I could perceive the context of it a lot more I understood how much she worked on it I understood you know what a big deal it was and it was for the public theater which is in New York is just an institution just a revered place to work so so so I really got it but again at 13 What great life wisdom, excuse me, for interrupting you, but what great life wisdom to have at 13 years old,

I can choose to have a different experience with whatever comes my way. I could choose misery or I can choose a different path. I do have that. For you to say that you've learned it now at 60 and remember it from 13, that's a long time. I'm just beginning to learn that. I'm in therapy. I'm not even kidding you when I say like two months ago.

I said to my therapist some form of, well, what if I just choose to experience this stuff differently than I'm experiencing it? That was two months ago. And this is the first thing you've done since. This interview right now. This right here is what I'm doing with that inspiration. I am choosing to enjoy this horrible time. Well, I'm glad, you know, again, because I've been in this industry, which is stupid,

This industry is the most ridiculous, just, you know, just people, I mean, part of what's fun about it is it's just ridiculous. You know, and I, I, that was always the sort of the deal. The deal, if you're going to get into this industry, it's going to be stupid and it's going to be unfair, and you can't expect it to be fair, because if you do, that will make you insane. And so, you know, I've been able to come at things with an enormous amount of positivity and let things go the same way. You know, I've managed to not bring a lot of bitterness into my life. And also, in many respects, I've been incredibly lucky. I mean, that I've gotten more than one opportunity to ever be on a TV show,

that I've gotten more than one opportunity to ever be in a movie, to be on Broadway. I mean, this is all, these are all amazing things. So I, you know, I, I, you know, I, it's not, it's not hard to be grateful for him. Look, every football game is a grind. And if you're like Dan and the crew, you know there's no such thing as one size fits all. Your sleep should be just as custom as coach's game plan. That's where sleep number comes in.

You get to call your own plays. softer, firmer, cooler, warmer, your side, your comfort, change it whenever you want. No more feeling stuck like a busted play. And for all the late night fights over the thermostat, Climate Series cools up 20 times faster than the competition. True temp betting kicks heat and humidity to the sidelines so you can actually stay chill all night long. Bottom line, sleep number is like having a sleep coach in your corner,

adjusting to you all night because your best game starts with the right rest. Why choose a sleep number smart bed? So you can sleep just the way that you like. The only bed that lets you make each side firmer or softer whenever you like. Your sleep number setting. Sleep number's biggest sale of the year is here. All beds on sale. Up to 50% off the limited edition smart bed.

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So between four years old and pretty and pink, You're just, you know you're going to be an actor. This is what you're going to do as a career. It's not going to be about schooling. It's not going to be about anything else. This is who I am and I'm this from four years old. Well, I didn't really definitively understand it as a career and as a pursuit until I was around 12. I was pretty late.

And, no, around 12, a friend of mine was going to a theater camp in upstate New York. and I was like, okay, I want to do that. And my mom, who was not a wealthy person, had to scrape together. It was a pretty expensive camp as summer camps go. And so she scraped the money together. And I went to a place called Stage Door Manor in upstate New York. And, you know, at that point, so many kids in that place were geared toward professional theater. They were thinking, I am, that's, and I just 100% fell into place with that.

I was like, yeah, I'm doing that too. And I had also hoped to, you know, I wanted to be an actor, but I also wanted, it was thinking about being a feature film director. I loved films and stuff like that. But I really loved performing. And that was what seemed to, to, I seemed to be the place of the most comfort for me. How about confidence in just going through the teen years? Oh my God. Well, okay, first of all, Seizure Manor, there was, there was 40 guys and, 230 girls. So, first of all, it was much easier for guys to get really good parts, which is unfair. And that's the way the business is and finally turning around, by the way. But it's been 50 years, you know, and it's, you know, much or way, way longer than that culturally. But so, so the guys would get a lot of really great roles. Also, half of the guys were not straight. So if you, if you were looking to date girls, this was, the, A fish in a barrel situation. So I got so much confidence. Also because it was a weird place where weird things were status symbols, you know, like if you got that great part, all of a sudden you had status, you know.

And that meant nothing at my school, you know, that. This is the coolest you've ever been. Yes. This is, indisputably, this is as handsome and it's sexy and as amazing as you've ever been. Yep. To his day. But it was great. It was an amazing experience.

It made me who I am. Did you have any idea could you have at that age an understanding of what John Hughes was or how good he was at what he was doing with Pretty and Pink? 16 Candles was the first thing of his that I saw. He was a writer for National Lampoon before that. And I recall, and my older friend, the one who had gone to the summer camp before me, he used to get National Ampoons from his older

brother, and I used to read the National Amputs because there was some nudity in them. I'm going to be 100% honest here. I think that's what you've... It's important that this is what they come here for right here. The porn that you found in your comedy magazines, this is the kind of expose that they expect from me. Yes, yes. This is going to be breaking the internet tomorrow. But John Pryor, Red Nash Lampoon for the Naked Ladies. At any rate, I, but John Hughes had some of his earliest writings published there, and I noticed them. There was a few pieces that I thought were really, really funny. So when 16 Candles came out, amongst the young actors, everybody was like, wow, this guy's great.

And I remember I auditioned for 16 Candles, did not. even get close to not even get a callback. But when Pretty and Pink came around, obviously, I did a little better. And by that time, I had already booked, I was doing Brighton Beach memoirs on Broadway, the Neil Simon play. So, you know, obviously I had made a, had a lot more experience. I read that your mother, after that movie came out, all it was was on her answering machine teenage girls calling and giggling because they found your mother somehow? Yeah, well, they used to have a thing called the phone book where people listed their names and their phone numbers and it was just there in a big book. And people and my mother was just in there.

And by the way, my mother, until they stopped making phone books, my mother was in the phone book. So, so yeah, she got a lot of calls. What can you tell us about that in experience that people might not know? About which entire? The pretty impingent experience. Oh, that people might not know? Hmm. Well, you know, movies are, high school movies are weird because you, most of the people that make

them are out of high school. They're not in it anymore. So for us, it was really important to capture. still being in it and really feeling like, like, really bringing some authenticity to it. And they shot in high school around, actually a high school in Hancock Park that I just, I drove by on the way to the studio today. As a matter of fact, I was like, oh, we shot there. But what was unusual for Pretty and Pink and still is incredibly rarely done was we had an enormous just a matter of rehearsal. The director, Howie Deutsch, had us get together and really tried

to spend a lot of time just letting us get comfortable with the dynamic. And he really encouraged Molly and I to hang out and have a real social shorthand with each other. And he was okay that Andrew and I didn't get along. Apparently, according to him now, he said, oh, I wanted you guys to hate each other. And I was like, oh, mission accomplished. He said, yeah, part of the reason I cast you guys was that there was always tension between you guys and that worked for the movie. I was like, oh, you're an evil genius, Howie Deutsch.

Or we just ended up hating each other. I don't know. The funny thing was he's not a bad guy. I found out later that he was going through a lot of really rough stuff at that time. I'm sorry to be smiling. I need to take the smile out of my off of my face. I was just smiling about the tent,

the idea of the tent. attention being real. Oh, yeah. The idea of, like, you actually hating somebody. I don't, when you walked in here, I'm like, that person's not physically, fundamentally capable of hate. Well, well, listen, mister, you're about to hear me unload. Well, no, the thing about it was, I come from the theater and I don't know if you've, have

you ever been involved in theatrical productions and stuff? I know a lot of people who come from the theater, so I have some fluency in the language. Got it. They're fun people. They're fun people. My son went to college, but even though it was an engineering school, I said hang out with the theater kids because they're the fun ones. Especially the ones who know that it's silly and ridiculous and what a wonderful way to make a living and aren't like flatulent with self-involvement. Yes, 100%.

So I was used to that feeling in the theater that you get that sort of camaraderie and that trust that you build when you're working with other performers and writers and all that stuff. and that wasn't there at all with Andrew. As I said, I later found out that he was already having issues with alcohol. He had a very rough relationship with his dad that was going through a very rough period at that time. So in retrospect, I understand why he was remote and he was not looking for, for, he didn't need a best friend at that point. He didn't need me to be his friend. He was just, he was showing, he was doing the job, you know. so I but I took it as what's up his ass you know and so I did not I did not get what he

was going through at all and Molly was always a person who didn't feel the need to be an extrovert either she made real efforts to she invited me out with her friends and stuff and said hey come see i'm seeing a band tonight want to come see i mean she made a lot of efforts uh uh to to make sure we we doesn't sound like a lot of fun though does it it's okay you're not you're not speaking negatively of it you're just speaking honestly of what the situation was it doesn't seem like it was the making of it if you're rehearsing all the time and now you're doing it with a couple of people around whom there's not total perfect chemistry of like where you know where there was arm in arm i no i i don't

No, I just don't want, I don't want it to, you know, Molly was great. I had issues with Andrew at the time, absolutely. He and I, by the way, have talked many times, and he's lovely, and he did the Brat, Brat's documentary, and we had a great time doing that. I'm not trying to get you to, you're trying. I'm not trying to get you to show me the dirty, the dirty underbelly of the making and pretty and big. No, but, you know, but I did have fun for, because I had a great time hanging out with

Annie Potts and I had a great time with Jimmy Spader. Please stop yelling at me. Please stop pointing at me. I had a great time. You need to understand that fun was had. At any rate. You scandalous

journalists trying to gotcha me as I knew you try to do. I thought you'd do it with the Charlie Sheen questions. Instead, you're doing it with pretty impank. I'm trashing poor Andrew McCarthy. No, I will not trash Andrew McCarthy.

We're nipping that in the bun. You're incapable of hate. We've already established that. Yes, exactly. So what do you think your career is going to be as you enter this phase? As you're heading into Pretty and Pink and what do your wildest dreams look like? Oh, oh, at that point? Well, I had a good feeling about Pretty and Pink because Breakfast Club had since come out.

Breakfast Club came out just after I booked Pretty and Pink. And it was, you know, an atom bomb in terms of teenagers in America. And so I thought, oh, okay, we're, this, this could happen to us, too, you know. So I had a good feeling about the thing resonating with people right away. And then after that, I, you know, my vision of my career was I really wanted to do a million different things. I didn't want to just be the funny sidekick. I just wanted to find a bunch of characters that I really enjoyed. And I did that.

But interestingly, I had a string of just bomb movies, just movies that, not in the good sense. They weren't da bomb. They just bombed. And they were all incredible learning experiences. and, you know, I, you know, met a lot of wonderful people and learned a lot of wonderful things. I mean, like, here's an example. I did a movie called Dudes with Penelope Sphiris. She's a really iconoclastic director.

She directed all the decline of Western civilization documentaries. And she had just done one of them when we did dudes. And it was a punk rock western. So I was like, what the hell is this? This is going to be fun and really interesting. And it was. But the production was horribly troubled. Just weather just ruined us for weeks. And so we were always behind the eight ball. And the movie you can really tell. I mean, we had to recut whole huge chunks and we had to drop sequences. And it was very frustrating. But also, I was just learning how to be a leading man in that. You know, and like I said, it was, it was a great way to make a lot of mistakes. Unfortunately, the movie did not, did not really work. But like Penelope, the next thing she did was Wayne's World, you know, was this just mega hit, you know? So I, you know, just, again, it's impossible for me to not feel gratitude because I got to meet

and see and learn from amazing people. So you're able in the moment to treat those failures as learning with gratitude or that's in retrospect? You have to experience the pain. You have to, you know, there is a mourning process that you have to go through because everybody had high hopes.

You don't get into a movie hoping that it doesn't, that it falls apart and doesn't work. I mean, like Superman 4, you know, I did the last Christopher Reeve Superman movie. And it's a mess. You know, they ran out of money. before they even finished it.

So the movie doesn't even make rational sense in a lot of places. And that makes me really sad. And I did, I had to mourn it. And it was a piece of my childhood because I had loved the original Superman the movie. It had meant a great deal to me in terms of what movies were

and what they could be. And that I was a part of that was amazing. But that I was a part of that. that that went down in flames, I did have to reckon with. And for a while, you know, I didn't, like, I didn't want to talk about it. You know, people bring it up now and I enjoy talking about it. But it did take me a while to mourn it. And now I sort of, now that I understand all the background stuff that happened behind the scenes, you know, again, I just, I learned so much from it. Do you know what it feels like? Have you had the experience?

with whatever it is, the perfect movie set is toward making a perfect movie in production so that things are humming along in whatever way they're supposed to hum along when an actor knows, as they very infrequently do, that they're in the middle of making a good movie. I don't, I've not spoken to many actors who often know they're in the middle of a movie that for sure will be good. That's tough. I felt that way in Pretty and Pink. I felt that way in Hot Shots, which was the first movie I did with Charlie Sheen, but most of the time. Those are hard to make, those sometimes you can't tell it all, that kind of movie, whether they're going to string together all of the funny correctly is, yeah, you're right.

It is to a certain extent. That script was so terrifically sustained in the humor. I mean, it was so funny, and, you know, as you were reading it, it was hilarious. that we all did feel, who were working on it, we did, we had a great time every day. And we did feel like, okay, the timing of this is great. And then the Gulf War broke out. We were like, oh, okay, maybe the timing wasn't so great. But it didn't stop the movie.

The movie ended up still being a huge hit. But I, you know, those were like the closest to feeling like, like, this is going to work when we're on the set. But like I did a movie recently called Big Time Adolescence with Pete Davidson and Sidney Sweeney and Machine Gun Kelly. And it was a no budget thing of a script that I liked, but it was a little kind of off-key coming-of-age thing. And, you know, we shot in Syracuse, New York, and they didn't even have money for trailers. I mean, literally, we would get dressed in, they would rent out somebody's family room in their house, and we would get dressed. just, you know, wander over there and Pete was smoking enormous amounts of pot and, you know, and then just commandeering a golf cart and driving around in Syracuse. And, and yet, that one came

out and was one of my favorite things I've ever done. It's just this beautiful little, perfect teenage movie that, you know, that's what I aspire to. But again, why was we? we were doing it had no idea. You know, I'm just going to show up and do the best stuff I can do. It's Rona Week. Now until Wednesday, rain or shine, you can always be building yourself a better summer. So, head over to Rona and save 30% on SICO endurance interior paint. Give that room you keep saying needs a fresh coat of paint, a fresh coat of paint. Build it right, build it Rona. Conditions apply, details in store, and more offers at rona.ca. I said interior paint, right?

You can get protein at home, or a protein latte at Tim's. No powders, no blenders, no shakers. Starting at 17 grams per medium latte, Tim's new protein lattes, protein without all the work, at participating restaurants in Canada. Well, speaking of having no idea, when you do the television show, who do you think you are, to find out about your life history, your family life history. What do you learn? Oh, oh my God.

Well, I accepted the gig because Lisa Kudrow literally, she's a producer on it, she literally just cornered me. I was like, you should do the show. And I'm like, okay, I'll do the show. But if you've ever seen that show, you get great trips on that show. They fly you amazing places. And I was hoping that it was like, this is going to be someplace great. You know, italy, let's go for Italy.

But I'm not Italian at all. And the only thing they did let me know beforehand was that we were going to go to Scotland. And I was like, oh, is my family, is this sort of a brave heart situation? Well, you know, was my forefather a fierce warrior? You know, and they flew me to Scotland. And it turned out it was totally a brave.

Braveheart situation. My nine times great-grandfather was an actual Scottish rebel. He was captured. He was sold to a company in the Massachusetts colony. He was shipped as cargo from England to Massachusetts. And he worked for the company for several years. The company went under, so he got freed from his indenture. and he started as a farmer in in Massachusetts and and and they went through my family

and we remained super duper Scottish Scottish AF as they say just very imbred amongst the Scots that had come to the United States but but it was it was they they they flew me to Scotland then then they retraced his path from being captured Richard back to England and then, you know, sending me across to Boston where he was brought to begin with and took me to the place where he worked, where the company worked. I mean, it was just to understand that kind of a journey, you know, and realized that my family's been here before America, before the United States was United States. That warrior, though, would weep at what his descendant chose as a career.

He might, but by the way, I did not say he was a good warrior. He did not, but he was captured. He got captured very early on. Apparently in the particular battle, it was very embarrassing because Oliver Cromwell sent the new model after him, and they attacked at night, which apparently just wasn't done at the time. You're just not supposed to do that. And so he was taken totally by surprise and captured. You were scared, okay, to say anything bad about Pretty and Pink behind the scenes,

and yet you take out one of your forefathers as a bad warrior. He was a very good farmer. He was a very good farmer. It doesn't change that he would be ashamed of what you chose to do. a living. Yeah, he probably would. He probably would. Was your mother, because she didn't exactly support you dropping out of college, right? Well, I never went to college. No, she, it was high school. Okay. So, forgiveness. I gave you extra education. I know. Nice try, mister. But she wasn't, she wasn't supportive of that, or she wanted

you to have a plan B, yes? Yes. Yes. And I, and I didn't actually have to end up dropping out of high school because I didn't actually get my first gig until like four weeks before high school ended. So that ended up not being a problem. But yeah, she was always, both my parents were supportive. They'd come up to the camp to see the shows I was in, stuff like that. But I could tell they were, you know, that there was a deep concern because I was about to enter a business that was deeply unfair and could, you know, really hurt, you know, can, you know, it has devastated some people, you know, if you don't, you know, get the emotional equipment to, to handle of how, how ridiculous it is.

And how rejection feels, right? Yeah. Do you have that emotional equipment? Like, you've developed it, right? Yeah, I'm used to it. I actually, interestingly, I, you know, in the last 20 years, I usually get offers instead of being asked to audition for things, but I actually prefer to audition because I'd like to show them how this is going to be because I've also had the experience of getting offered apart, taking it and showing up the first day and realizing this may not be a perfect fit. And that's, you know, really scary. so I you know I don't you know I I I you know obviously there's things that I was like oh I wish that worked you know like a recent thing I auditioned for was Brian Cranston when they did all the way at the LBJ

movie there was a part in it that I really liked and and I went in and you know I was all bright-eyed and bushy-tailed and I just didn't get it you know and that's that's what happens So, you know, you just have to sort of, you know, they're, I've been lucky enough that, that, that, that one of the, one of the few good products of having success early is you realize, okay, I've been there. I can't achieve this. It's possible. So there is always that sort of certainty that, that, you know, I did it. I did it at one point. I can probably do it again. Helps, too, to have the knowledge that the business is unfair right when you're starting because you come from a show business family. You mentioned Lisa Kudrow.

You came close to getting Chandler in Friends? No. That's the thing. It's a fun story. It's become this big narrative that I could have been Chandler. Basically, unfortunately, the reality of that narrative is, I auditioned for Chandler, didn't get it. that's boring that's not a fun narrative but that is in fact what occurred but you don't know how

close you were or weren't so i can make it close to make my podcast more entertaining exactly that makes it a lot more you were just so you were right there but you're just saying no it was just an audition i was thinking about it is are there any uh there are some extenuating circumstances to it though that make that give it that the reason that it's that it's that it has a toehold as a narrative was because I was in London when it happened. I got literally in the middle of the night, Marta Kaufman called me. I was doing a play there and said,

will you audition for this tomorrow morning? I was like, it's 3 a.m. here in London, just so you know, there's a time difference. So she faxed me the pages, and the next morning I went in and read. And I don't think I was particularly good, but I did my best because I did love the pages. And they sent the tape to the United States, and it got stuck in customs.

So they never saw it before they made the thing. However, but the reason is that I, a friend of mine, one of my, one of my counselors from Summercam ended up becoming a casting director for Warner Brothers. And he was in on that whole process. And he said, no, no, no. They wanted Matthew Perry very early on. They'd worked with him before on some other stuff. And he's a flipping, he was genius, you know. So, you know, it would have, I would have had to have been quite a dark horse to have gotten that.

Do you have an almost that stands out, like something that you were close to getting that ended up being in it, that you really wanted that ended up being a big thing and you either could have seen yourself in that? Or you say, no, that person pretty much crushed it the way that they did it. I have a fun story. I was auditioning for two movies at around the same time. I was auditioning for No Small Affair, which was a movie that Columbia was doing. And I auditioned for The Mask, a movie with Cher. Or no, not The Mask, Mask, Mask, with Cher, that was being directed by Peter Bogdanovitch. And I was a huge fan of Peter Bogdanovich, but I was very intense.

intimidated by him. But he was, God, that movie, you were young. Yeah, I was pretty young. But, you know, it was about a kid. You know, Mask is about a kid, you know, with a very rare disease that deformed his face in particular. And I was auditioning both of those, for both of those, and they offered me no small affair one day. And I was like, oh, my God, I'm getting offered the lead in a big movie. And but Peter Bogdanovich's office was calling and saying, no, don't take it because we want you to meet Cher for mask. And I was like, yeah, I got to take the bird in the hand here. And Eric Stoltz ended up auditioning and getting it.

And Eric Stoltz is wonderful in that movie. He's fabulous. It's a great movie. And it's a terrific movie. I am sad because it's a terrific movie. And no small affair is an okay movie. but that's also a seminal role right it's a very it's a very memorable role because there's never been anything like that before since really and that's that is the biggest deformed

star head character that there's been elephant man arguably but uh they're both terrific movies um but it's but they're both really really good movies uh and uh so that that was the closest to a a one that got away situation um because Who knows if I'd met Sherry? I'm still laughing at myself because of the eloquence involved with deformed head man character and your correction of the elephant man. Take us to where it is you are in your life right before two and a half men. What is happening in your life then and what do you think is going to become of your acting career? Well, I had had a spurt of successes I had Pretty in Pink, and I had done a bunch of films after that, as I said, that were all troubled in various ways.

But then I did hot shots, and so I was kind of, I was sort of back a little bit. But then I started doing television, and I had two shows. in a row that were on for a season and then canceled. And that's actually worse than doing a pilot that nobody sees, that doesn't get picked up, because when you're on a show and people see you, and then they cancel it, the industry gets the perception that the public just didn't go for you, you know, and that happened to me twice. So suddenly my career was stone cold after that.

That's silly, though. You would expect more from leadership, executives, producers, they should know more than that about the industry they're in. No, everybody's, everybody's guessing. Everybody, you know, everything seems obvious in hindsight, you know. But while you're making all these decisions, they're all look, everybody's looking for reasons to say no to things. And that was their reason was, you know, he's, you know,

he's gotten a couple of big shots and didn't work. And so things got very cold for me. I remember there was a three years stint where I only worked three weeks for the whole three years. Are you agreeing with these people now? He's cold. Are you, is doubt creeping in? Is anything happening? Yeah, doubt was creeping in and, and yeah, and money was getting tight for the first time.

And I'd always made, I'd always way underspent my, you know, I, because I got lucky early, I saved, you know, and I'd always, you know, live beneath my means and, and, and, uh, but after a long time, you start running really low, you know, and, and, um, and. Oh, so you're wondering, is it over? Yeah, I'm thinking I am not equipped for any other profession at this point. So I wonder if this will turn around. I still had a basic confidence in myself, and I did a weird thing, which was we just have a thing called pilot season, which we don't even actually have anymore now that TV is so balkanized. But there was a time when all of the shows were casting at once. And it was like a stampede for actors.

And agents were nuts at this point because they were all trying to lock down their money for the next year. And so it's a crazy time for actors. And I decided that instead of being picky about things, I was going to audition for everything. Every part that I was vaguely right for. I'm just going to audition because people don't, people have forgotten what I can do. And so I went out on everything. And, you know, I was going to turn, if the part was really wrong, or if I didn't like the script, in the end, I'd say no.

But what I ended up doing was I ended up getting nine offers that year, which is unheard of. And I just kept turning them down because I knew I wasn't actually the right guy or the project just wasn't the right thing. But you're also running out of money or not? Money's getting low. Are you thinking about money in ways you haven't had to in a while? Yeah, no, I had, I had, I had, when my son was born, I, I sprung for a very large house.

I bought Kathy Bates' house as a matter of mind. And, and that, and I was starting to realize, okay, that was a mistake. And I'm going to have to, living here is not going to be a possibility. So, so I was thinking, okay, I have the house to sell. So, you know, I wasn't going to be destitute. But you're scared. But you're scared. But you're scared. But you're scared um i and i i i uh i was scared and uh that season uh it it's one of the few times in show business where what i wanted to do what i did intentionally worked as i intended in that turning down on those things made people just was like chum in the water made people uh excited to see me and you know and so when i so so in the the last two shows of the season that we're casting were two and a half men and Battlestar Galactica. And I went on on both of them and got test offers on both of them the same day, and I had to choose one.

And because I'd work with Chuck before and I'd work with Charlie before, and Jim Burroughs was directing the pilot of two and a half men, I chose two and a half men. But by the way, I loved Battlestar Galactica. I loved that show and would have felt incredibly lucky to be a part of that, but was not meant to be for whatever, for whatever reason. But that was one of the few times where, you know, that, if I hadn't gotten it, I would have said, this was the dumbest, this is the dumbest tactic ever tried. I should have taken four of those other jobs. But they, but in that particular case, it worked. and I got the gig that was the right thing. You expected it to be what?

Two and a half men? Yes. Well, what I loved about it was that the, I enjoyed the script, but you know, it's the odd couple. It's an odd couple script, but with a kid, you know. So I thought in order to not be that, it's really going to depend on what Charlie and I do.

And after my first audition with Charlie, I was like, oh, okay, this thing is going to kill. This is really going to roll. Yeah, but kill and be what it was, it still had to have exceeded your expectations. Yes, it did. By leaps and bounds? Yeah, because I'd been on sitcoms that I thought were terrific in the past, but that just viewers didn't. Number one for how long? Oh, I don't know.

We were, we were, we were, we only were number one for like two or three seasons only. You know, we were, you know, because everybody loves Raymond was number one when we first started and it stayed that way for, you know, we were on for two seasons behind everybody loves Raymond. And then, obviously, you know, it was easier for us, you know, once they ended their run. So you have huge chemistry with Charlie. He's clean for how long? Like how many years are you guys working just effortlessly and well together? He had been clean for two years when we started. And he lasted another two years before he and Denise split.

And he clearly had started using again. And those four years felt like the whole thing was humming. Everything was going great. You're on top of the world. It feels like success. Enjoy going to work every day. Yes. Are you noticing when he's coming into work?

Oh, he's relapsed? like you know no no he was at work he was really on top of it um uh you know when his when his marriage fell apart obviously something was up and we were trying to you know you know marriages don't work sometimes and so i'm not going to say oh it's because he's he's relapsed you know because i knew how important his sobriety was to him so i was hoping that wasn't it um it was it took years before i realized oh he's using again um because he was so functional at work he was really good at it. And even up until the end, when it was getting, you know, when he was acting out in public and getting arrested and all that stuff, it was still on the set. He was still

pretty much together. I mean, the cracks were showing in the final season, but, you know, he's still, he's still performed when he needed to. Were you mad at him? Oh, sure. Oh, sure. the biggest most compelling emotion is terror because I thought he was going to be dead. We all did. And that's what we were, you know, every day just waking up to and the second you open your phone, you're like, is this the day that I'm going to see that he's gone? You know, and by this time, you know, his dad had performed with us and, you know, we were close with Brooke and with all, you know, with everybody. in his life with Ramon his brother with you know I mean so so you perceive that it's not just your job you know that that's at stake it's it's this person you know and and you feel so friend someone you care about someone you love yeah terror yeah so we were all really scared and and yeah there was some anger because you know he was he was he was he was on top of the world, the show could have, you know, could have run way longer if he wanted to, you know,

and he, you know, there was no reason for us to, to stop if he, you know, if he could keep it together. But it was interesting because, like, he would find things to be mad at in terms of, like, the writing or stuff like that. And it was, it was very frustrating because he acted like, and that the, you know, the, and the writers were incredibly differential to him. All he had to do was say, hey, listen, this, you know, this feels kind of shallow. I don't, this doesn't really make sense to me. And they would have, you know, jumped over the moon for him. But he just, he wouldn't say anything.

It was so weird because he'd complained to me backstage. And then the second we were in rehearsal and we ran through the scene and it got laughs, he would just not say a word. And I was like, but if you don't tell them. They listen to you. You're the star of the show, you know. So it was very frustrating. And I didn't like, when he was starting to have his breakdowns,

I didn't like the attention that it was bringing to the show and to me, conversely because all of a sudden, like the paparazzi were coming after me in the street, and I didn't like that at all. So, you know, or like he'd go on the Alex Jones show. And, you know, talk about, you know, 9-11 was a setup or whatever. And it's like, okay. You know, that was a fun argument in the makeup room. But, you know, it, you know, I'm really glad that he's, he really seems to have turned over a new leaf.

And, you know, he's still, he's still chugging along. Have you found healing and forgiveness from where you're angry? was because you could, I mean, technically, you could have kept going for a really long time. And I imagine once he left the show that you felt the weight of the loss in a way that continuing it could have kept you still angry at him because you're doing a lesser version of the show that you wanted to be doing. Yeah, I had some frustration, mostly with the sort of persona he adopted after the show, the Tiger Blood persona just, I knew it was bullshit. And so hearing him just constantly spewing it, was just like,

shut up. But so, you know, so, you know, at this point, I am, you know, there's no point in maintaining anger about that kind of thing. And, and I am happy that he's, that he's doing well. And he's reached out a couple of times. I don't know that I'm comfortable being a part of his life, but I do wish him the best.

Oh, so you haven't, you haven't, when he reaches out, you don't return? I haven't as of yet. You know, maybe there'll be a time when I'm cool with that. I have failed to mention by way of conclusion here, your new passion for the true crime podcast. This is something that has consumed America, all true crime podcasts, but yours is the man who calculated death. Your involvement with this project means what to you, and why should people find it right now? It's an amazing podcast. It's one of the, it's a true story that basically a friend of mine, a friend of my wife's actually, Suzanne Rico, is a wonderful journalist.

She was an anchor person here on CBS News here in L.A. And one day we were talking and she casually dropped that her grandfather was one of Hitler's most important scientists. And I was like, I'm sorry, you're going to have to back that one up, Suzanne. Turns out, Suzanne's grandmother had been killed mysteriously in a bombing at the end of World War II. And the family had always been sure that she was killed in revenge because her husband had created the V1 buzz bomb, which was a transformative weapon in World War II. Still, it's the first cruise missile. It's absolutely revolutionized warfare. Her grandfather was a genius.

but unfortunately he was working for the Nazis and he was a Nazi. Just casually dropped that. Just casually dropped that. So Suzanne had been for the last few years, her mother had passed away and her mother had left an unfinished memoir. So Suzanne had,

Suzanne's mother had asked her to finish it on her behalf. So Suzanne had been researching her family and she had all this on tape. So she made it into an amazing podcast. And it's, so it's a little bit of true crime because she does solve the mystery of how it happened, but it's

just an amazing family history. It's incredibly brave. And she made an amazing piece of work. Your family's history could have been brave, but you said that your warrior ancestor wasn't a good warrior. That's going to be a different podcast. That he was conquered, that no one knows

if he actually knew how to fight in any way. He may have been a coward. John, thank you for the time. I know that you have to leave. I'd still be asking you questions. Thank you for being with us. The pleasure was mine. Thank you.

It was mine. It wasn't just yours. No, uh, it was mine. I disagree. I'm keeping the pleasure over here. I've got just as much of the pleasure over here. You get the pleasure. I win again.

That's all that matters. I am the pleasure king.