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.
Denise Richards Divorced Sheen In 2006, Alleging A Wide Range Of Abusive And Generally Horrific Behavior On Sheen's Part
Denise Richards and Charlie Sheen's 2006 divorce was public and ugly. Many of the allegations Richards made against Sheen are horrifying. She claimed Sheen was violent and addicted to gambling, paid sex, and adult media content. She recalled an incident which took place in front of their children in which Sheen shoved her to the ground and said, "I hope you f*cking die, bitch." Her court filings also included transcripts of abusive voicemails left by Sheen and described the explicit material he allegedly viewed online, which included pornography of people who did not appear to be of age.
Charlie Sheen Was Arrested On Christmas Day For Assaulting His Then-Wife Brooke Mueller
In addition to the numerous assault accusations Denise Richards leveled at Sheen, he already had an extensive rap sheet of violence against women. In 1990, he shot his then-fiancée, Kelly Preston, which he claimed was an accident. In '94, Sheen was sued by a UCLA student who alleged he hit her in the head when she refused to have sex with him; the case was settled out of court. In '96, Sheen was arrested for assaulting actress Brittany Ashland, who received seven stitches in her lip from an altercation in which she said he threatened to kill her; Sheen pleaded no contest to battery charges, earning only two years' probation. Then came his marriage to and divorce from Denise Richards. Fast-forward to 2009.
On Christmas that year, Sheen was arrested for allegedly holding a knife to then-wife Brooke Mueller's throat, threatening to kill her. Sheen ultimately pleaded guilty to misdemeanor third-degree assault but was only sentenced to three months probation in addition to attending rehab and anger management classes.
Charlie Sheen Asked Jon Cryer To Hide His Porn When His Then-Wife Denise Richards Came To Set
In his 2015 memoir, So That Happened, Cryer described an interesting encounter with Sheen early in their tenure together at CBS:
One day during the first season of Two and a Half Men, I got a knock on my trailer door. It was Charlie... he seemed panicked. "Dude! Dude! I need your help."
"Sure thing," I said, and ended the cell phone call I was on. "What’s going on?"
He handed me a heavy shopping bag. "Denise is coming over," he said, "and I need you to hide something for me."
Oh, boy, I thought. If this is drug paraphernalia … "Is it legal?" I asked.
"What? Yeah, oh, yeah. It’s legal. Hey, thanks."
He left, and I had to look. By legal, he meant barely legal. It was a bag filled to the brim with porn... I was prepared for the weirdest, but it really was all pretty tame, some of it just topless mags. Really, if this was the worst I’d have to deal with regarding Charlie’s vices, bring on the bags of porn for me to hide.
Jon Cryer Asked Charlie Sheen For Advice On How To Pay For Sex
Cryer's memoir unsurprisingly dished quite a bit about the goings on behind the scenes of Two and a Half Men. Perhaps more surprising was the amount of embarrassing stuff he revealed about himself, such as his foray into the world of soliciting sex in exchange for cash. Cryer admitted to being "an emotional basket case" after his divorce from British actress Sarah Trigger, and he needed to "get [his] equilibrium back."
He went to Charlie Sheen for advice on how exactly to pay for sex, and Sheen directed him to his personal favorite online services. When a woman with a "sexy Finnish accent" came to Cryer's house for the first time, he reportedly enjoyed the experience.
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."