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.”