Given the reputation of its star, Charlie Sheen, it should come as no surprise that Two and a Half Men has some dark behind-the-scenes stories (though even shows as seemingly innocent as Seinfeld had their own issues).
Sheen's character Charlie Harper imitated his real-life counterpart fairly closely. Harper was a womanizing, substance-abusing gambler who would eventually meet an untimely death, but it didn't quite capture just how monstrous some of Sheen's alleged actions were. Perhaps even more surprising is costar Jon Cryer's affection for Sheen, which he spoke about at length in his memoir, revealing some pretty shocking things about himself in the process. Somehow, Ashton Kutcher was the most boring dude on the show when he joined the cast in Season 9.
If you still care about one of the most overrated shows of all time, be warned; there are spoilers for the series finale ahead.
Sheen Often Showed Cryer Nude Pictures Of Women
After Charlie Sheen's marriage to Denise Richards ended, he regressed to maximum Sheen. The first signs were when he started showing Cryer pictures of women's genitalia:
...[H]e'd show me a picture he'd taken of somebody's vagina. It was always a perfectly nice-looking vagina, but I would invariably think, Why just this, and not the rest of the person?
And what do you say in that moment? "Thank you for that vagina picture"? "How long have you been seeing … it"? "Please tell me she was awake"?
Unfortunately, it's never made clear if the women in the pictures were awake or consented to the photographing in any way.
Cryer Broke Up With A Girl After Discovering She Had Previously Dated Sheen
After Cryer decided to once again start seeking legitimate romance, he met a woman named Stephanie and the two hit it off. They started dating and Cryer brought her to the set of Two and a Half Men. When he introduced her to Sheen it became clear the two knew each other. Sheen later told Cryer he had actually dated Stephanie before, but things went sour when he tried to convince her to have a threesome. The story as written by Cryer says as much about him as it does Sheen:
Charlie said, "Well, I wanted to bring another girl into bed with us, and she was not happy about that." And then he looked me straight in the eye and with no trace of irony, said, "So heads-up on that." I went home that night and broke up with Stephanie.
Cryer claims he ended things with Stephanie because dating Sheen should have been "upfront information."
Sheen's Huge Raise To $1.8 Million Per Episode Came Immediately After His 2009 Arrest
In May 2010, a few short months after his arrest for domestic abuse, Sheen became the highest paid actor on television at the time. His salary bumped up to $1.8 million per episode on a two-year contract. Cryer was making around $600,000 per episode at the time. "I immediately began contemplating a series of well-publicized drunken brawls in retirement homes or possibly leading cops on a destructive car chase just prior to my next contract negotiation," joked Cryer in his book.
In Late 2010, Sheen Was Forcibly Hospitalized After Another Alleged Assault
In October 2010, Charlie Sheen reportedly paid adult film star Capri Anderson $3,500 to spend the evening with him in New York City. The night ended with Sheen exploding in a fit of rage, trashing his room at the famed Plaza Hotel. Anderson claimed he threatened to kill her, and she locked herself in the bathroom for safety. When police came, they took Sheen to a local hospital for a psychiatric evaluation.
After the incident, Sheen allegedly texted Anderson, offering to pay her $20,000 to stay silent. Instead, Anderson filed a harassment complaint with the NYPD, prompting Sheen to sue her, claiming extortion.