Everything Jon Cryer Said About Charlie Sheen, Two and a Half Men in New Docuseries

For eight years, Cryer was side-by-side with Sheen at the top of television's highest-rated comedy, Two and a Half Men. Unfortunately, what started as a joyful sitcom dream turned into chaos, uncertainty, and ultimately calamity as Sheen's personal demons and behavior brought the show to an abrupt halt in its 8th season.

Two and a Half Men would ultimately carry on for quite a few more years, but not with Sheen. After an explosive and very public battle with show creator Chuck Lorre, the highest-paid actor on television at the time -- scoring a tidy $2 million per episode -- was fired in March 2011.

Ultimately, Ashton Kutcher would replace Sheen on Men and the sitcom would continue for four more seasons. Sheen, meanwhile, would continue to spiral out of control, giving erratic television and radio interviews while coining catchphrases like "Winning!" and "tiger blood," before launching a disastrous live tour.

From sharing in his successes to watching on the sidelines as his former scene partner very visibly melted down in the public eye, Cryer peels back when things started to go so visibly wrong and what it was like being in the eye of the storm as it was happening in Netflix's no-holds-barred docuseries into Sheen's life of luxury and madness.

In his own publicity tour in support of aka Sheen, as well as his new memoir The Book of Sheen, the actor admitted that of all the people who'd agreed to take part in his documentary, Cryer was the only one he'd not been able to speak with directly.

Talking with People, Sheen said that he "didn't have the right number" for Cryer, but was appreciative of his involvement. He said that after seeing him speak "so honestly and very compassionately" in the film, he wrote to him, "Hey, thank you for your contributions, and I’m sorry we didn’t connect personally. I hope to see you around the campus."

As for the content of Cryer's contribution, Sheen said, "He was in the line of fire with all that stupid s--t going on, and it was affecting him and his family and his career and all that. I can’t debate anything that he said."

He also appreciated a moment of insight from Cryer that he felt deeply in relation to his struggles with addiction. "He said, 'He’s a guy that doesn’t believe he deserves the things he has, or that it was earned,’ and I was like, 'Whoa,'" Sheen told People.

Perhaps more than anyone Charlie Sheen has acted with professionally, Jon Cryer has spent more time working alongside him. After eight tumultuous years together, Cryer got to see much of the best and worst of his former co-star, but still he's not sure he ever really came to know the real Sheen.

"I worked with Charlie Sheen for eight years. And if you wonder what it's like to work with Charlie Sheen for eight years, when I started, I had hair," Cryer quipped at the top of Netflix's two-part aka Charlie Sheen -- the title also seemingly unsure if it knows who the real Charlie Sheen is.

Cryer admitted to "some trepidation" in even taking part, "because part of the cycle of Charlie Sheen's life has been that he messes up terribly, he hits rock bottom, and then he gets things going again."

"He brings a lot of positivity in his life, and that's when he burns himself out again. He just can't help but set that house on fire, and I didn't want to be a part of that cycle," Cryer explained. "I'm not here to build him up and I'm not here to tear him down. But I sure hope this doesn't go bad."

He went on to explain Sheen's life, as he saw it, as the actor walking a tightrope. "You wanted to like him, because he was really charming and smart and terrific in what he does as an actor. But also there were incidents that you were like, 'Wait, what happened?'"

In that instance, he was referring to the accidental shooting of Kelly Preston way back in 1990. As people wondered if he shot her intentionally, Preston herself came out and insisted the gun fell out of his pocket.

"Kelly said, at the time, 'Oh no, that was an accident.' So there's this part of you that goes, 'Okay?' There's always this tightrope of, 'I don't know the whole story. Is he the guy who he appears to me to be, or is there some much darker thing going on?'" Cryer said. Unfortunately, despite working together for nearly a decade, Cryer never really got a clear answer.

From the moment they met, Cryer was left with this uncertainty about the surface Sheen and the man underneath. He shared that right out of the gate, before shooting had even begun on their sitcom, Sheen told him, "I know there's a lot of stories about me.' I've been sober for 2 years and it's incredibly important to me to be faithful to that. And I'm really trying to change my life."

Cryer thought it was "interesting" that Sheen "felt the need to express that to me ... to say, 'I'm gonna be serious about this, Don't be worried.'" Of course, as the years carried on, there would be plenty for Cryer to worry about, with the actor describing Sheen as "an icon of decadence."

"Everybody expects this, the lothario guy, this guy who's got the quip handy, he could party all night, show up an hour late, breeze through makeup, saying hello to everybody, who's always gonna be the cool guy in the room, said Cryer. "But you start to realize, 'There's a lot going on there that he's covering.'"

He explained his perception of Sheen, saying, "Charlie's actually this mass of fears. Once I understood that, I understood a lot more about Charlie. But he goes in and out of being able to have a healthy way of dealing with that and then an incredibly destructive way of dealing with that, which is, you know, the drugs and the partying."

For Cryer, he felt that he started to see his co-star unravel when Sheen and Denise Richards began their family. The couple, who wed in 2002, welcomed two babies during the show's early years, daughters Sami in 2004 and Lola in 2005, and by the following year, they were divorced.

Talking about when Richards appeared on the show with Sami as an infant, and everything felt "easy," Cryer said that at the same time, he started to "sense there were things that he was just never going to be that suburban, being more of just a regular married guy. I felt like it might be, you know, fighting against the tide."

The actor then recalled one awkward moment that marked a shift. "At one point, Denise showed up unexpected, and I get this frantic knock on my door and it's Charlie. I open the door like, 'Hey, what's up,' and he's looking around frantically -- I mean the guiltiest look around, I mean, it's like a cliche -- and he said, 'Hey man, can you hold this for me?' It's a brown paper bag and I'm like, 'What is it? I'm not gonna hold it. Is it legal?' And he said, 'No, it's legal, it's legal.'"

Cryer said that he agreed, ultimately, "so I put it in my dressing room and I closed the door, and the bag is just sitting there, looming. And I was like, 'What could possibly be so embarrassing that Charlie Sheen doesn't want his wife to see it?' So finally, I couldn't help it and I looked in the bag. It was legal. It was 'Barely Legal,' the porn magazine. I felt really bad that Charlie's relationship with Denise was going south."

For her part, Richards said in the documentary that she felt Sheen was "sabotaging the success and sabotaging our family" as the actor admitted that this was when he'd started using drugs again. As for whether he felt he was becoming addicted, Sheen said, "I thought about it, but I negotiated the hell out of it with myself, you know."

As the show continued to be a huge success for CBS, Cryer continued to get hints that things weren't perhaps as perfect in Sheen's outside life as they were on set. He'd said that still to this point, whatever was happening in his personal life had not impacted what was happening on the show -- yet.

As an example, Cryer recalled when Sheen went on to remarry after his divorce from Richards, wedding Brooke Mueller -- who had a history of addiction herself -- in 2008. "I was not able to be there because I was on a movie, so my wife went," Cryer said. "My wife called me afterwards and said, 'Oh my God.' 'I have concerns,' is what my wife said."

"She said, 'Okay, I just wanna tell you the toast that Martin Sheen made at the wedding," he continued. "and I said, 'Okay,' and I braced myself. He apparently stood up, said, 'I hope you two know what you're doing,' and sat back down. That was the entirety of Martin Sheen's toast at Charlie Sheen's wedding."

Shortly after their wedding, Sheen and Mueller welcomed twins Bob and Max in early 2009, with Sheen saying that the boys had some serious medical concerns while they were babies. With Two and a Half Men still a ratings juggernaut at this time, he admitted to starting to feel "a ton of resentment that the show still mattered that much when the star's kids, at birth, were in tremendous peril."

Sheen also said that Mueller fell off the wagon first, and that it's when he caught her and a friend doing cocaine in the bathroom that he followed suit. "I start banging on the door and they're like, 'What do you want? Don't be a party pooper,'" Sheen recalled. "And I said, 'If you're gonna do this s--t in my house, you need to stop wasting it, and you need to do it properly. Let me show you how to cook this s--t up. And it was on.'"

It was as his addiction was starting to spiral out of control that Richards shared that Les Moonves, then head of CBS, showed up at Sheen's house with the head of Warner Bros. television and gave Sheen an ultimatum. They were either going to release a statement that he was going to rehab and the show would resume when he was done, or the show was canceled.

"He's in the midst of falling apart in every way that I can imagine, and he's renegotiating his contract for another year of a show that I'm supposed to be on, too," Cryer said, as Sheen remembered feeling like he was done ... but then there was that $2 million per episode.

"Apparently, they had pre-sold a couple of extra seasons of the show so, you know, it was worth their while to spend this astonishing amount of money on Charlie," Cryer added, saying that he wasn't getting paid nearly as well. "His negotiations went off the charts because his life was falling apart. Me, whose life was pretty good at that time, I got a third of that."

At the same time, Sheen said that he told them, "I get there's a lot more juice to be squeezed out of this thing, but, uh, I don't know how much juice is left in me. And I do fear if I go back it's going to go terribly wrong.' I said those words."

Richards, too, said that she was upset about the new contract, feeling, "Why are you guys putting him on a show right now? Like, he's not well." She added, "But they just see the money and just want to keep on going."

Talking about his highest-ever payday, Sheen now concedes, "Yeah, it was a lot. It was just too much money to give a guy like me in that mindset at that time. It was a recipe for disaster."

Two and a Half Men creator Chuck Lorre admitted that after Sheen had started using again, "I was certainly aware that things were coming unglued and, you know, I was probably in a great deal of denial about it as well."

Cryer said that the work impact started slowly, with Sheen missing a day of rehearsal here and there. "In the back of your mind, you're always wondering, well, I obviously want to give him the benefit of the doubt. He shows up on Friday when we actually shoot in front of the audience and he knows his lines and he does a great job. I really don't know."

He also admitted to living in denial at the time, in part, perhaps, "because your livelihood depends on his livelihood." He recalled TMZ reporting that Sheen's Mercedes was at the bottom of a ravine as the first time he started to really worry about his co-star.

"I'm like, 'Holy crap, did he drive off a flipping cliff?'" Cryer said. "So I go into work that day and he comes in, he's like, 'Hey man.' I'm like, 'Hey…' 'Cause I'm looking him up and down to see if there's scratches. 'Cause I assumed that he was loaded, he drove off the cliff, somehow survived, and then had to climb up the cliff to get back home."

As it turned out, someone had stolen Sheen's car -- and then the exact same thing happened again, which let Cryer know that he really didn't understand Sheen at all, as he always just seemed kind of chill about the craziness that always seemed to surround him.

"He just appeared to take it in stride. There's so much about his life that I will never understand," Cryer admitted. "I could not live with that in my life. That somebody stole my Mercedes and drove it off a cliff twice, would be something that would make me have a hard time sleeping at night."

From there, he said that "it was starting to show in the work," with Sheen's timing off, him struggling more to get his lines right. He also felt Sheen was "overcompensating for being loaded" by being extra friendly with everyone on the set.

"He would come in and he'd be super-friendly to everyone, 'Hey everybody, how's it going?' He would hug crew members who were like, 'Hey, hi, Charlie. Good to see you,'" Cryer remembered. "That's when I was worried about Charlie every day. Every day I was like, 'Is this the day that we're gonna lose him?'"

The end came shortly after when Sheen was suddenly rushed to the hospital in early 2011 after he collapsed in pain amid a drug-fueled party. "We were all very sure that he had OD'd and that he was probably very near death. And it was terrifying," Cryer said. "But he just kept saying, 'No, no, no, I'm in the hospital now, but next week I'll be ready for the show.'"

It was at this moment that Sheen was faced with the aforementioned ultimatum from Moonves and the head of Warner Bros. Television, ultimately choosing the option that would have seen the show continue.

"We're all sort of, you know, we're looking at each other like how do you deal with this, how do you deal with somebody just so intent on bringing themselves down?" Cryer said of the sentiments around the show at the time. At the same time, Sheen was "going on these crazy rants" in interviews, like on Alex Jones, which was raising even more alarm.

"I later found out part of the reason he was going on those crazy rants was that he was using testosterone," Cryer said. "That that combined with the drugs he was doing at the same time, and drinking, which he was all doing again. Led him to just go on these manic episodes."

As part of these rants, Sheen started to lash out at Men creator Lorre. "What I've come to really embrace in all this time since, so much of the anger in my personal life and the anger and the frustration of two failed marriages and four new children and just never-- not finding any real success in those pursuits," Sheen admitted, "I decided to take out on Chuck."

Within six weeks of Sheen's collapse during his party and the ultimatum, the show was shut down. Two and a Half Men was put on hiatus in February 2011, effectively cancelling the rest of its eighth season. A month later, Sheen's contract was terminated, setting up the soft reboot of the show with Kutcher and Cryer.

The spiral, for Sheen, was just continuing to grow. After his firing is when he started dropping viral phrases like "Winning!" and "tiger blood" and "Adonis DNA," going viral for an unhinged 20/20 interview and somehow gaining a rabid fanbase for his escapades to the point he launched a live tour.

"So much of the public were cheering it on," Cryer said of Sheen's very public meltdown. "They wanted to see the trainwreck because we were in this new age where they could see all of it."

He thinks that people connected to that version of Sheen who'd flipped off his show's creator and the head of the network because they were able to live "the life that they want" vicariously through him. So when he got fired, "they were mad that anybody was holding him to a limit. That anybody was stopping him really pissed them off."

"You wanna see a certain creature, if you will, you want to see a certain bad person doing crazy, insane, bad s--t and glamorizing it in some bizarre way and feeding it, and then at the same time, um, demonizing," added Mueller of that time in Sheen's life.

While everyone saw it as Sheen speaking truth to power and being "a breath of fresh air," as Cryer put it, he saw things differently: "No, he's a guy who got everything he ever wanted from this business. He just lost it and he's having a tantrum."

Sheen admitted that he can't even look at footage of himself from that time anymore, as it gives him "the shame shivers." He said that it "would've been nice if somebody had stepped in and just was like, 'Whoa, hey, whoa, this is not-- this is not a spectacle for everyone's folly. This is a man that's in trouble."

Ultimately, despite all of the chaos that he found himself in the passenger seat for, when Cryer looks back on it, he doesn't hold bitterness or resentment. "I don't like to think of people by the worst thing they've done and the worst person they've been. Because we're all complicated, and we've all done things we're not proud of," he explained.

"I try not to judge," he continued. "Seeing somebody you know is capable of being a regular guy go off into that, you sort of go, 'Oh, okay. Something is broken in him that may not ever be able to be repaired.'"

aka Charlie Sheen is now streaming on Netflix.