Jon Cryer dishes ‘Pretty in Pink,’ ‘Superman 4’ and Charlie Sheen anecdotes on ‘Howard Stern’

Jon Cryer was on Howard Stern Tuesday morning to promote the paperback edition of his 2015 memoir So That Happened, a book that laid bare a number of juicy details from his life in the Hollywood trenches. After breaking through as the lovable “Duckie” in Pretty in Pink, Cryer's career went into virtual freefall as his next several films — including the legendary flop Superman IV: The Quest for Peace — tanked at the box office. His fortunes turned only when he booked the soon-to-be-mega-hit series Two and a Half Men in 2003, but the years in between were filled with major missed opportunities and various other career disappointments — by his own admission, he worked just three weeks as an actor over a three-year period.

So what dirt did he have to spill during the Stern Show sit-down? Below I've rounded up the juiciest portions of the interview, from his Pretty in Pink breakthrough to the legendary drug-and-press-fueled meltdown suffered by his Two and a Half Men co-star Charlie Sheen in 2011.

1. He lost out on the role Chandler Bing on Friends because his audition tape got held up in the mail.

Cryer: “It got stuck in customs. They Federal Expressed it from — I was doing a play in London at the time, and I get a call from Marta Kauffman at 3am…and at that point [the show] was called Six of One. It was not called Friends. And she asked if I could audition for this character Chandler, and I was like sure, yeah, what time?…I went in the next morning and I was totally out of it, and I auditioned with the casting director…and then it was her job to get it to Fed Ex, and Fed Ex it to the United States…

Howard: “And they never got it, they figured you're probably not interested and –“

Cryer: “No, it's not that they — they got it late, they already cast Matthew [Perry] when they finally got it.”

2. He thought the original ending of Pretty in Pink, which sees Molly Ringwald's character picking Duckie over Blane (Andrew McCarthy), worked well despite the fact that test audiences rejected it. 

Howard: “When the director comes to you and says 'listen, audiences don't like you getting the girl,' do you take that…as like, 'what am I, a monster?'”

Cryer: “You know, there was a little bit of that. And Howie Deutch, the director, at the time to his credit was super sweet about it. But yeah, I had a little bit of that disappointment that you know, oh, I was sad that the audience couldn't invest in me as a romantic interest in that instance.”


Howard: “Have you ever seen that version, by the way?”

Cryer: “Yes, as a matter of fact. I saw — there was a print done of that, that was done for test audiences, that was the one that test audiences did not like…I was shown, they did like a special preview, as a matter of fact, for me […] they showed it to me, and I thought it worked! I thought it was adorable!”

3. He had the unfortunate distinction of starring in Superman IV: The Quest for Peace just a year after hitting it big with Pretty in Pink.

Superman was just gonna be a lark, and I was gonna get to work with Gene Hackman, and they had gotten the whole cast together from the original, and Chris Reeve had written the story to the script, so everything was feeling like it was gonna be great, like everything was auspicious,” said Cryer of the legendary flop. “But the people making the movie was a company called Cannon Films. And Cannon was famous for doing shitty movies. And turns out there was a reason that they were famous for this. They were really bad at making movies. And they ran out of money about halfway in, and so they started cutting all these weird corners, and cutting out huge chunks of sequences that were supposed to be shot, and just never got shot.”

4. His 1987 movie Hiding Out was partially responsible for the demise of short-lived distributor De Laurentiis Entertainment Group. 

Adding to his post-Pretty in Pink career woes, the film — which saw Cryer starring as a state's witness forced to assume the identity of a high school student — flopped at the box office, helping sink the studio that bankrolled it.

“I did a movie called Hiding Out that there was a famous producer named Dino De Laurentiis, who was this Italian producer, very flamboyant…and his studio financed Hiding Out and was expecting big things from it, because it's 'Ducky gets his own movie!'” said Cryer. “And I was the star of that movie. And it opened so badly it sank the studio. The studio ceased to exist after that.”

5. He lost out on a role in the hit “Brat Pack” vehicle St. Elmo's Fire to…Andrew McCarthy.

Pretty in Pink wasn't the first time McCarthy was favored over Cryer. A year before that, the former won the role of Kevin in the iconic 1985 film over his future co-star. Cryer had this to say about the casting in a discussion about his early career:

Cryer: “I was auditioning for St. Elmo's Fire. That's, yeah, so.”

Howard: Who'd you lose that out to?

Cryer: Andrew McCarthy. There you go. There you go.

6. He backed out of auditioning for Reservoir Dogs because he couldn't understand the script.

Though producers of Quentin Tarantino's directorial debut practically begged him to read for the role of Mr. Pink (a part that ultimately went to Steve Buscemi), Cryer was so baffled by the screenplay that he used an opportune call from his sister as an excuse not to audition.

“I was flying to New York on a Saturday, and I got this script right before I got on the plane, and they said, 'they want to meet you on Sunday,'” Cryer recalled “It's the only day that this young director can meet with people in New York. That's the only day. You have to do it. And I was on the plane, and I tried to read the script, but if you saw the movie, it's all over the place. And you're like, what are these people talking about? What? There was a robbery, but then there's cutting an ear off. What is going on here?…It's very complicated. And I just couldn't handle it on flight 007 going into JFK. So I read as much of it as I could, but I couldn't finish it. And I thought 'oh god, I'm gonna go into this thing not really prepared.' 

“The next morning though, I get this call from my sister that her mother-in-law is ill, she's gotta go out and visit her in Long Island. So can I take…care of her daughter? And I go, oh, I have a good reason that I can't go to this audition now, I've gotta take care of my niece! So I call up the producer, and I'm like, 'aww, I'm sorry, I can't audition for this thing.' And he's like, 'please, please, we really want you to come in!'…finally I just had to beg off and not audition for what ended up being a brilliant movie.”

Despite missing out on the role, which could have theoretically helped re-launch his then-fledgling film career, Cryer sounded unconcerned about what could have been, telling Howard: “The nice thing for me is that I know that I wouldn't have got that part even if I showed up that day…I really don't. I truly don't believe I would've.”

7. CBS head Les Moonves didn't originally want him for Two and a Half Men.

Citing an article in Newsweek magazine that dubbed him a “Show Killer” (though the article in question appears to have been published after Two and a Half Men became a hit), Cryer said that his reputation for starring in failed TV shows like Partners, Getting Personal and The Trouble with Normal made CBS head Les Moonves wary of casting him in Men

“A lot of these networks, they know that the actors circulate, and they do shows, and the shows flop, and then you know, and everybody knows, it's an industry,” said Cryer. “But that [Moonves] had sort of a special antipathy toward me was a little weird. And it was partially, after three shows that tanked, I had been given the name The Show Killer, basically. And you need so many things to go right in order to have a hit, that there's a point at which you just try to eliminate the shit that's gonna make it hard.”

The best part of the story? According to Cryer, Moonves “doesn't remember not wanting me now.” A true executive.

8. He was forced to choose between Two and a Half Men and Battlestar Galactica.

Though he was offered roles on both series simultaneously, Cryer chose the former based on his past professional relationship with Chuck Lorre and the chance to work with legendary TV director James Burrows — though he lamented having to pass on Battlestar.

Howard: “Here you had a choice between Battlestar Galactica, or a show with a guy who parties too much, and also Les Moonves doesn't really want you. I'm surprised you didn't go for Battlestar Galactica.”

Cryer: “You know, yeah, I was torn. Also because I loved Battlestar Galactica. I loved the original. And the new script already was great…it was very tough.”

9. Hugh Grant almost took over Charlie Sheen's role on Two and a Half Men before Ashton Kutcher was hired.

Cryer initially scoffed at the idea of landing an (admittedly fading) movie star like Grant following Sheen's departure, but the rom-com king actually did sign on to star in the series before backing out at the last minute. “They negotiated a contract, he was signed,” said Cryer. “I got confirmation from Chuck: 'He's on the show.'”

As for the character Grant would have played, Cryer offered the following description:

“They had come up with a really fun idea that this incredibly charming British guy had come to Malibu…because he wants to rent a place while his daughter goes to Pepperdine, and he works at the embassy, and he's just incredibly cool, and [my character] Alan just thinks, 'thank goodness somebody's gonna help me pay the rent here because I can't afford it.' And then it turns out he's a con man. He's full of it, and I'm stuck with him because he can still pay the rent. And it was fun! It was really fun, it was a fun character.”

10. Charlie Sheen apologized for calling him a “troll” during that infamous 2011 meltdown — but only in the context of pitching him an unofficial Two and a Half Men spinoff. 

Howard: “Did he ever apologize to you, after this whole thing went down and Ashton Kutcher replaces him, did he ever have a moment where he just said, 'you know Jon, we work together, I called you a troll, I apologize.' Was there a moment?”

Cryer: “Yeah, I talk about it in the book. There was a moment. And interestingly though, what I didn't talk about in the book, and I only realized it actually fairly recently was, at that point — the thing is, when you're dealing with somebody with an addiction problem, you never know what is sincere and what is when they're just trying to get to the next thing. And he said it in the context of wanting to do another show with me. And you know, he wanted to do a show, basically the Harper brothers are back together again, this other stuff never happened. Basically start a new universe.”

Howard: “You mean he wanted you leave the Chuck Lorre show and…”

Cryer: “…and just do a show with him. And I thought he was joking at the time. I laughed. But I do believe he was sincere.”

11. Martin Sheen gave undoubtedly the best toast at Charlie Sheen's 2008 wedding to Brooke Mueller.

“At his [wedding]…Martin Sheen, who's been through this before to some degree, his toast to the bride and groom was — he stood up and everybody's getting ready, cause this is President Bartlett from West Wing, he's about to lay something down,” recounted Cryer. “And he says, 'Hope you kids know what you're doing.' And he sits back down.”