Jon Cryer: From Dating Demi Moore to Getting Prostitute Pointers From Charlie Sheen

Photo: The Howard Stern Show

In the wake of Jon Cryer’s tell-all memoir “So That Happened,” the acclaimed actor had a slew on intriguing stories to discuss with Howard on Tuesday morning. Jon opened up about his early days as Duckie in “Pretty in Pink,” his awkward love affair with Demi Moore, and the rise and fall of his “Two and a Half Men” co-star Charlie Sheen, complete with how they used to look at pictures of random vaginas together.

Turning Down “Battlestar Galactica” for “Two and a Half Men”

Photo: CBS

Before landing the role of Alan Harper on the hit CBS sitcom “Two and a Half Men,” Jon had reached an undeniable rough patch in his career – between 2000 and 2003, Cryer says he only worked three weeks in three years. He had shot a string of failed television shows and had gained a reputation as being TV pilot poison.

“I had three shows that all got on the air in a row and all of them went down in flames and after that, that was when it just dried up,” Jon said. His money disappeared and he considered trying to teach acting but wasn’t sure if he’d even be able to do that.

2003 ended up being a good year for Jon after he got offers for two pilots: one was “Two and a Half Men,” the other the reboot of “Battlestar Galactica.” At the time, it might have made more sense for him to choose “BSG,” since according to Jon, CBS president Les Moonves didn’t want him on his network.

“A lot of these networks, they know that actors circulate,” Jon explained to Howard. “But that he had some special antipathy toward me was a little weird. After three shows that tanked, I had been given the name the Show Killer.”

That unfavorable nickname was bestowed upon Jon by Newsweek, who included him in a feature about failed TV actors that were causing American television to suck.

Despite Moonves’ objections, Jon was given the role opposite Charlie Sheen and “Two and a Half Men” became an instant success. Everyone, including Jon, assumed Sheen had settled down and become a hard-working family man. But his behavior would soon change.

Charlie Sheen, Prostitutes, and Vagina Pics

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The on-screen chemistry between Cryer and Sheen continued even after the cameras stopped rolling, but Jon told Howard he noticed a change in his co-star when Charlie began discussing conspiracy theories.

“The time I started to worry is when [Charlie] went on ‘The Alex Jones Show’ talking about 9/11 and that he thought it was a conspiracy,” Jon said.

Charlie’s personal life was also beginning to crumble after his very public divorce from Denise Richards. But even with his life as chaotic as it was, Jon admits Charlie was still a professional during tapings.

“He still seemed very even-keeled and he was always great to work with,” Jon said. “Even during the craziness. On the set, he was still bringing it although something was off.”

The “Two and a Half Men” cast grew concerned for Charlie, as did many of his friends and family. Jon recalled attending Charlie and Brooke Mueller’s wedding and being excited to hear the toast from Charlie’s dad, Martin Sheen, famous for delivering long, eloquent speeches as President Bartlet on “The West Wing.” All the elder Sheen said as he raised his glass: “I hope you kids know what you’re doing.”

With Charlie and Jon both becoming single, the two started to explore relationships with other women. Whether he wanted it or not, Jon was soon getting love advice from Charlie, which included recommendations on prostitutes.

“If prostitution had a chamber of commerce, Charlie would be the ambassador,” Jon said.

Jon wrote in his book about how he did hire a hooker one night, but what started off as a night about sex led to a discussion and debate on finances, with Jon suggesting she invest her money in real estate and the prostitute vehemently disagreeing. Jon made sure to include a request in the foreword of his book for his kids to skip over this story.

In addition to good prostitutes, Sheen also used to share photos of girls with Jon, but only of their vaginas.

“He would just show me a picture of a vagina,” Jon said. “I don’t know what I’m supposed to say. Like, yay vagina! I like vagina.”

This is the End…Or Not

After Charlie lashed out at executive producer Chuck Lorre and called Jon a “traitor” and a “troll,” Charlie not only lost Cryer’s support, he lost the studio’s support. Warner Bros. fired Charlie from “Two and a Half Men” in a move that Jon says was the right thing to do. But would the show go on without Sheen?

“I got this cryptic text from Chuck Lorre saying, ‘I think we may not be done yet,'” Jon said. “I didn’t know what that meant.”

Cryer called Lorre and asked for clarification. Lorre explained that they had found someone to take Charlie’s place on the show – Hugh Grant. Jon laughed out loud after hearing the name.

“There’s no way we’re getting Hugh Grant,” Jon remembered thinking. “I did not think Hugh Grant would want to do it.” The character written for Grant was a charming British con artist and even after negotiating a network contract, Cryer proved to be right in predicting Grant wouldn’t want to do the show – he backed out, leaving the network scrambling to find someone else.

Awkwardness With Ashton and Demi

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The person who did end up sharing the sitcom spotlight with Jon was Ashton Kutcher, who helped keep the show a ratings success. But while the two worked well together, there was something problematic for Jon about being around Ashton.

“There was a little bit of discomfort since he was now married to the woman I dated back when I was 19,” Jon said. That woman was Demi Moore, Jon’s co-star in the 1984 movie “No Small Affair.” While shooting that film, Jon began a romance with Demi off camera and assumed he was her boyfriend. Her only boyfriend. He soon found out he was wrong.

“I found out from her housekeeper,” Jon told Howard. “I showed up at her house and I was like, where is she and her housekeeper said, ‘She’s out with her boyfriend.'”

Jon admits he was heartbroken and became the “standard hurt little bunny boy” but confronted her anyway. Demi told him she did not think they were exclusive and that ended their love affair. Unfortunately, the two still had another month of shooting together, including a love scene.

He’s Not Gay, Not a Republican, and Not Matthew Broderick

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Perhaps it was his first major role as Duckie in “Pretty in Pink” that’s led many people to think that Jon Cryer is gay in real life, when in fact both Jon and his character in the ’80s film are straight. Jon told Howard that even his “Pretty in Pink” co-star Molly Ringwald was confused about his sexuality.”She didn’t think [Duckie was gay] until I was cast in the character,” Jon said.

Rumors also started to spread that Jon was a card-carrying Republican, but he thinks he knows how that one began.

“Years ago I went to a John McCain fundraiser,” Cryer said. “This was not long after 9/11 and he was one of the few politicians who was against torture.” Jon is also against U.S. forces using torture so he wanted to get some face time with the Arizona senator. He confirmed to Howard though that he does not consider himself to be a Republican.

As for being confused for Matthew Broderick, that actually helped him early on in his career. A young Cryer used to work as a theater usher and had several people mistake him for Broderick, who was starring in “Brighton Beach Memoirs” on Broadway at the time.

“Why am I moonlighting as an usher if I’m this Broadway star,” Jon joked.

Soon after, Jon auditioned to be in “Torch Song Trilogy” and literally took writer Harvey Fierstein’s breath away as soon as he walked on stage.

“He thought I was Matthew Broderick,” Cryer said.

Jon then became Broderick’s understudy in “Brighton Beach Memoirs” though he never got any stage time.

“It’s a very weird job,” Jon said. “It’s like being a relief pitcher who never goes in.”

Be sure to grab a copy of Jon’s new memoir, “So That Happened,” for more great stories.