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Given the reputation of its leading 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

Photo: Two and a Half Men/CBS

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

Photo: donhall16/Flickr/CC BY 2.0

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

Photo: Two and a Half Men/CBS

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

Photo: Two and a Half Men/CBS

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

Photo: Two and a Half Men/CBS

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

Photo: Two and a Half Men/CBS

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

Photo: Two and a Half Men/CBS

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

Photo: Two and a Half Men/CBS

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.

Charlie Sheen Returned To Work Almost Too Ravaged By His Lifestyle To Function

Photo: Two and a Half Men/CBS

Cryer described what Sheen was like when he returned to work after his arrest and subsequent raise:

Charlie didn’t look so good as we started our eighth season in the fall of 2010—gaunt, pale, sallow, even sweaty occasionally. He started talking to himself. But most of all he just looked thinner, in a not-good way…

His timing started to go off, too… Charlie just wasn’t hitting the jokes the way he used to. It was as if his psyche had been sped up.

One time during rehearsals to choreograph the movement for a scene, he asked, “Can I just stand next to this couch?” He wanted to hold on to it for the duration of the scene.

Cryer’s Lackluster Response To Sheen’s Alleged Abuse Against Mueller Was Eyebrow-Raising

Photo: Two and a Half Men/CBS

In his memoir, Cryer recalls his reaction when he found out about Sheen’s arrest for domestic abuse:

Alarmed and freaked out, I texted him: Dude, my thoughts are with you. If you need to talk, give a call; if you’ve got bigger problems, call me when you get back.

A few minutes later, Charlie texted back: Thanks bro. Yikes—f*kk me, wut a bad day … I’m flying home tonite. I’ll try to call over the weekend. Shower rape was bad but the food was okay. Hair and makeup for mug shot got there too late.

Situations like this are rough on your sense of friendship and loyalty, because the allegations are serious, yet you know Charlie and Brooke are a drug-troubled pair, and Charlie’s your longtime friend who was proud of his sobriety, but that doesn’t mean he didn’t do something to her, and you should give a woman the benefit of the doubt when she’s been abused, and oh, boy . . .

Cryer’s consternation was clear, but despite their friendship, it’s a little difficult to justify such congenial texts between the two after Sheen had threatened to kill his wife.

Sheen’s Relationship With Showrunners Began To Devolve Rapidly In Early 2011

Photo: Two and a Half Men/CBS

By February 2011, Sheen had pretty much hit rock bottom (again). He was reportedly fired from his show for giving rambling interviews to every media organization that would listen and demanding that he should receive another raise, saying in one interview:

I’m not angry, I’m passionate. Everybody thinks I should be begging for my job back and I’m just gonna forewarn them that’s gonna be everyone else that’s gonna be begging me for their jobs back. I’m a man of my word, I’ll finish the TV show, I’ll even do season 10, but at this point because of psychological distress, I want $3 mil an episode, take it or leave it.

Look at what I’ve been through. [I make] roughly [$2 million] now. I’m underpaid right now, for sure. If you look at the money that [the producers] are making yeah, it’s ridiculous. I’m tired of pretending I’m not special.

Sheen Didn’t Cross The Line With CBS Execs Until He Called Show Creator Chuck Lorre A ‘Clown’

Photo: Angela George/Wikimedia Commons/CC BY-SA 3.0

After a long history of violence against women, including arrests during his time on Two and a Half Men, the powers that be at CBS decided Sheen had finally crossed the line in early 2011. Some believe it had more to do with Sheen calling creator Chuck Lorre a “clown” than the actor’s crimes.

The studio, however, claims in its dismissal letter that Sheen’s lifestyle began to take its toll on the show, offering the following statement to Sheen’s lawyer:

Your client has been engaged in dangerously self-destructive conduct and appears to be very ill… His declining condition undermined the production in numerous and significant ways. Warner Bros. would not, could not, and should not attempt to continue ‘business as usual’ while Mr. Sheen destroys himself as the world watches.

Sheen Lambasted Ashton Kutcher For Years After Kutcher Replaced Him On The Show

Photo: David Shankbone/Wikimedia Commons/CC BY 2.0

Over the course of a few years, Sheen made repeated comments on Twitter about Kutcher being a “lame sidekick,” once tweeting, “quit barfing on my old brilliant show.” Kutcher understandably became fed up, and on an interview with Jimmy Kimmel in 2014, said of the fallen star, “Dude, shut the f*ck up! Seriously, like. Enough already. Like it’s like three years later and you’re still blowing me up on Twitter. Like come on dude, really?”

Initially, Sheen was actually apologetic, tweeting, “I was pissed at other crap & took it out on you.”

But he quickly undercut that apology with a follow-up tweet: “but news flash Dood, you ever tell me to shut the F*** up, EVER again, and I’ll put you on a hospital food diet for a year.”

Ashton Kutcher Took The Job As Sheen’s Replacement Solely For The Money

Photo: Two and a Half Men/CBS

Kutcher accepted the role of billionaire Walden Schmidt in 2011, playing the character from Season 9 through the show’s 12th and final season. But Kutcher didn’t want the job. In a 2017 interview with Howard Stern, Kutcher admitted that his agent convinced him to take the role solely for the paycheck. If his $755,000 per episode salary wasn’t enough, he was set to earn royalties from syndication worth millions of dollars. Despite his movie career, Kutcher decided he couldn’t walk away from that kind of coin.

Sheen Mouthed Off About Everyone And Everything

Photo: Two and a Half Men/CBS

In January 2017 radio interview, Sheen was still saying awful things about Chuck Lorre (including “Suck my f*cking butt”), but he took a different (and surprising) tact when it came to Kutcher:

I was stupidly mean to him, because I overlooked the difficulty of taking over a show — which I did myself, I took over Spin City when Michael J. Fox was too sick. I should’ve been nicer. He was tasked with such an uphill struggle, and I was mired in my own ego. For that I am regretful.

This moment of self-reflection from Sheen may be considered shocking, especially considering his long and apparently remorse-free history of assaulting women.

Sheen Was Invited Back To The Show For The Finale, But Declined As They Wouldn’t Do It His Way

In the series finale of Two and a Half Men, the audience learns that Sheen’s character Charlie Harper never actually died, but was instead imprisoned by his crazy admirer, Rose (Melanie Lynskey), who was holding him against his will in a well in her basement a la Buffalo Bill. The show closes with Charlie Harper (only shown from the back as it wasn’t actually Sheen) ringing the doorbell of his old house, but before anyone answers, a piano falls on him and kills him. The camera then pulls back to reveal Chuck Lorre in the director’s chair, who turns to the camera and says, “Winning!” before he suffers the same fate as Charlie.

Lorre released a statement after the show about Sheen’s absence:

I know a lot of you might be disappointed that you didn’t get to see Charlie Sheen in tonight’s finale. For the record, he was offered a role. Our idea was to have him walk up to the front door in the last scene, ring the doorbell, then turn, look directly into the camera and go off on a maniacal rant about the dangers of drug abuse. He would then explain that these dangers only applied to average people. That he was far from average. He was a ninja warrior from Mars. He was invincible.

And then we would drop a piano on him.

We thought it was funny.

He didn’t.

Instead, he wanted us to write a heart-warming scene that would set up his return to primetime TV in a new sitcom called The Harpers starring him and Jon Cryer.

We thought that was funny too.

Angus T. Jones Wanted To Leave The Show In 2012 After He Found God

Photo: Two and a Half Men/CBS

Angus T. Jones played Jake, the kid everybody knew and loved, starring on the show from the age of nine. But the older he got, the more problematic his job became. In a 2012 interview, Jones said, “I’m on Two and a Half Men and I don’t want to be on it… You cannot be a true God-fearing person and be on a television show like that.” He ended up leaving the show the following year after the Season 10 finale, only to return in the series finale two years later. Leaving the industry sounds like it was good for him, as he told People in 2016, “I got pretty doomsday with my thinking for a long time, but now I’m having fun and enjoying where I’m at. I no longer feel like every step I take is on a land mine.”

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