So Jon Cryer at 92Y Happened

The Emmy-winning comedic actor elaborated on the many career stories he shares in his new book, 'So That Happened: My Unexpected Life in Hollywood.'
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“I jumped in front of the train.”

Jon Cryer 92Y Photo

Jon Cryer demonstrating his jumping-in-front-of-the-train move at 92Y. (Photo: Laura Massa/Michael Priest Photography)

It may sound like a poetic alternative ending to Two and a Half Men, considering Charlie Sheen’s character was once believed to have been fatally struck by a train. However, Jon Cryer is talking about an improv-class exercise from his time at Stagedoor Manor, a performing-arts youth camp known for its celebrity alumni.

The class’s instructor, Jack Romano, had set the scene as a subway platform, and while the students had been instructed to nonverbally act out fear of a serial killer, Cryer had decided his character was the serial killer, complete with whistling “Strangers in the Night.” As Romano indicated the train was coming into the station, Cryer leapt off the stage to his character’s death, and to the toupee-destabilizing shock of Romano.

“For years after that, this became this legend at the camp that I had so stunned Jack Romano,” Cryer said proudly. In fact, the story even made it into a book about the camp, called Theater Geek. However, the gasp-inducing jump was attributed not to Cryer, but to another famous Stagedoor Manor alum, Robert Downey Jr.

“So I had to write a book.”

And that’s the very reason Cryer was speaking to an eager crowd in 92Y’s Weill Art Gallery on Monday night: to discuss his new (and first) book, So That Happened: My Unexpected Life in Hollywood, and to answer questions from moderator Ramin Setoodah, senior editor at Variety and former senior writer at Newsweek, the very publication that once labeled him a "show killer.”

Jon Cryer 92Y Photo

Ramin Setoodah and Jon Cryer at 92Y. (Photo: Laura Massa/Michael Priest Photography)

This designation came, of course, after starring roles in four failed TV shows and before the hugely successful 12-year run of Two and a Half Men, which had its series finale in February, and for which Cryer won two Emmy awards.

In So That Happened, Cryer writes — and spoke — candidly but carefully about his evolving relationship with his original Two and a Half Men costar, Sheen; from how CBS’s Les Moonves originally didn't want Cryer for the role of Alan Harper because the combination of him and Sheen was just "too much ‘80s baggage,” but how their comedic rapport was undeniably effortless; how Sheen was exactly two years sober on the date of their first photo shoot, but how Cryer and so many others missed the little signs of that sobriety slipping away; how he feared the show was inevitably over once Sheen left but feared far more for his wellbeing.

“I’ll always have hope that he’ll change his mind and want to be sober again,” Cryer said.

Despite Sheen’s chaotic departure, the show did, as they say it must, go on. At first, Cryer recalls, it almost went on with Hugh Grant, who was signed “for about an hour and 15 minutes.” Ultimately, though, Ashton Kutcher became Cryer’s new Two and a Half Men costar, playing Walden Schmidt, in 2011.

“The strangest thing for me meeting Ashton was I used to date his wife,” Cryer said, referring to Demi Moore. “When he was seven years old.”

Cryer revealed that he had dated Moore on and off after being cast as costars in his first feature film, 1984's No Small Affair. However, she wasn't the first actress to read for the role of Laura Victor. First, Cryer screen-tested with Ellen Barkin.

Jon Cryer 92Y Photo

(Photo: Laura Massa/Michael Priest Photography)

“Ellen Barkin is Ellen Barkin. She’s this super-sexy panther of a woman,” Cryer said, playing it as coyly as possible with his parents, wife and young daughter in the 92Y audience. But when asked how much chemistry they had while running through a scene that involved a passionate kiss, Cryer responded, “None whatsoever.”

Barkin wasn’t the only actress with whom Cryer didn’t have audition chemistry. Reading with Molly Ringwald for the first time at his Pretty in Pink callback, they “never had that sort of spark,” which would have been ideal considering the original ending, as Cryer explained, had Ringwald’s character, Andie, end up with his character, Duckie.

“We actually shot a different ending to Pretty in Pink,” Cryer said of how their characters come together at the prom. “It was supposed to be a victory for underdogs,” with the entire prom stopping and staring as Andie and Duckie slow-dance to David Bowie’s “Heroes” in the moonlight.

As adorable as that sounds, it had to be scrapped.

“The first time they played the movie for a test audience, they actually booed. We ended up having to reshoot the ending with her ending up with Andrew McCarthy’s character,” Cryer recalled. “But I have to say, for me, it’s ended up being great because there’s still such fierce Duckie partisans to this day.”

It wasn't until years later, however, that Cryer found out why he and Ringwald didn’t have that aforementioned spark at their audition. She admitted that, at the time, she wanted a different actor to play the role of Duckie.

That actor? Robert Downey Jr.