He went on to establish himself as one of the most talented comedic actors in the business, ultimately culminating in his award-winning turn as Alan Harper on the massively popular sitcom Two and a Half Men. In 1986, Jon Cryer won over America as Molly Ringwald’s loyal and lovable best friend, Duckie, in Pretty in Pink-a role that set the tone for his three-decades-long career in Hollywood. Now he’s opening up and sharing his behind-the-scenes stories in a warmly endearing, sharply observed, and frankly funny look at life in Hollywood. If it can happen in show business, it’s happened to Jon Cryer. "I don't know if you recall, but this was during the firestorm of all the craziness when Charlie Sheen left the show and he was a possible guy taking over, so we had a meeting to see how it would go," he said.The Emmy-winning star of Two and a Half Men opens up in this warmly endearing and frankly funny memoir about life in Hollywood. "It was a little bit awkward because she and I had dated when he was 7, so there was that aspect," he joked.
On Live! With Kelly and Michael Tuesday, Jon shared new details about his fling with Demi. "In our first meeting, we're trying to have that let's-create-that-chemistry meeting, and the whole time I'm looking at him, waiting for him to drop the bomb." "It was awkward in that I'm not sure she even told him that we dated," the actor told Entertainment Tonight Monday. When Ashton, 37, replaced Charlie Sheen on CBS' Two and a Half Men in 2011, Jon was afraid to tell him that they shared a mutual ex. Jon, 49, recalled that he and Demi, 52, dated 30 years ago, around the time that they co-starred in the 1984 romantic comedy No Small Affair. In his newly released memoir, So That Happened, Jon Cryer revealed that he once romanced his Two and a Half Men co-star Ashton Kutcher's ex-wife, Demi Moore.
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