The core of the Two and a Half Men cast was comprised of a woman-abusing drug addict, a nine year old who would eventually leave the show after finding God, and a sex-purchasing bystander and complicit supporter of his co-star's deranged antics who just happened to write a tell-all memoir after the fact. With that in mind, it should really come as no surprise that there are myriad Two and a Half Men dark behind-the-scenes stories (though even shows and seemingly innocent as Seinfeld had their own BTS issues).
Charlie Sheen's character Charlie Harper imitated life fairly closely as he was a womanizing, substance-abusing gambler who would eventually meet an untimely death, but it didn't quite capture just how much of a monster the man truly was. Perhaps even more surprising is Jon Cryer's affection for said monster, 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 took over Sheen's role in Season 9.
Here are some mind-blowing stories about one of the most overrated shows of all time. If you care for some reason, 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. The range of credible allegations Richards made against Sheen are horrifying. She claimed Sheen was violent and addicted to gambling, paid sex, and adult sexual 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 voicemails Sheen left her, in one of which he allegedly said, "You're a coward and a liar and a f*cking n*gger alright so f*ck you." She also described the explicit material she found in his search history, concerned that the people on camera were underage, describing girls with "braces, and no pubic hair" as well as gay porn featuring young men 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 assaults of which Denise Richards accused 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, but it ended their relationship. In '94, Sheen was sued by a UCLA student who alleged he had 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 adult film star Brittany Ashland, who received seven stitches in her lip form an altercation in which she said he threatened to kill her; Sheen pleaded no contest to battery charges, earning a laughable $2,800 fine and two years' probation. Then came the 2006 Denise Richards stuff. Fast-forward to 2009.
On Christmas that year, Sheen was arrested for allegedly strangling and holding a knife to then-wife Brooke Mueller's throat, threatening to kill her. Sheen ultimately pleaded guilty to third-degree domestic violence. Once again, he was not imprisoned, but attended a outpatient rehab in Malibu.
Charlie Sheen Asked Jon Cryer To Hide His Porn When His Then-Wife Denise Richards Came To Set
Cryer described an interesting encounter with Sheen very early in their tenure together on CBS. Whether or not it was a regular or one-time thing is unclear, but here's how Sheen asked him to hide his porn:
"One day during the first season of Two and a Half Men, I got a knock on my trailer door. It was Charlie — my trailer was next to his — and he seemed panicked.
'Dude! Dude! I need your help.' 'Sure thing,' I said and ended the cellphone 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. The bag was 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
Jon Cryer released a memoir in 2015 titled So That Happened in which he, not surprisingly, dished quite a bit about the goings on behind the scenes of Two and a Half Men. Perhaps more surprisingly was the amount of embarrassing stuff he revealed about himself, one particularly noteworthy entry being his foray into the world of soliciting sex in exchange for cash. Cryer admitted to being "an emotional basket case" after his divorce to 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 (because if that's really what you're trying to do, who better to consult?), and Sheen directed him to his personal favorite online service. When a woman with a "sexy Finnish accent" came to Cryer's house for the first time, he described it as a "friendly experience." When he subsequently "went to her place, which probably wasn't really her place," he claims to have spent 25 minutes of his hour "helping her with financial planning."
In summary, Cryer apparently wants you to focus on how much he helps the women he solicits for sex.