In the first few seasons of Two and a Half Men, the show’s stars Charlie Sheen and Jon Cryer shared an undeniable on-screen chemistry. However, years after Sheen lost his role on the show following an epic meltdown, Cryer reveals what really went on behind the scenes. And what he has to say about his disgraced co-star may come as a shock.
In 2010 Charlie Sheen was at the top of his game. He was earning a staggering $1.8 million for each episode of his show Two and a Half Men. As a result, he held the honor of being the highest-paid performer on television. Furthermore, his performance on the series had earned him two Golden Globe nominations and four Emmy Award nods.
However, halfway through the eighth season of Two and a Half Men, the hit sitcom was placed on hiatus. The move was part of a tumultuous chain of events that began in early 2011 and culminated in Sheen’s eventual dismissal from the show. However, before that happened, the actor gave a series of fiery interviews, even taking a series of potshots at the show’s producer, Chuck Lorre.
As Sheen’s personal and professional issues boiled to the surface, his Two and a Half Men co-star, Cryer, realized that his job was linked to the erratic leading man. As a result, the media storm caused by Sheen’s volatile behavior no doubt felt very real to him. And recently, Cryer has revealed what it was really like to be in the eye of that storm.
Cryer was born in New York on April 16, 1965. His father, David, was an actor while his mother, Gretchen, worked in theater, co-writing — and starring in — the stage musical I’m Getting My Act Together and Taking It on the Road. Consequently, it seems that Cryer got a taste for showbusiness early on in life.
When Cryer was 12, he decided that he wanted to follow in his parents’ footsteps and become an actor. In order to learn his craft, he subsequently spent his summers at theater camp. And thanks to his mom and dad’s links to Broadway, Cryer was eventually able to get a foot in the door of the industry.
Cryer got his first break on Broadway in 1983 bagging roles in two popular comedies, Torch Song Trilogy and Brighton Beach Memoirs. In both plays, Cryer was a stand-in or replacement for the actor Matthew Broderick, whom he resembled. And like Broderick, is seemed that Cryer was also destined for a life in the movies.
Just like Broderick, who found widespread fame in the 1986 film Ferris Bueller’s Day Off, it was a John Hughes movie that gave Cryer his breakout role. Also in 1986 Cryer starred in Pretty in Pink as “Duckie” Dale. However, while the film was well-received, Cryer’s subsequent movie roles were not nearly so financially successful.
As Cryer’s movie career floundered, he made the transition into television. But even in this new medium, he struggled to hit the ground running. He was part of four comedy series which suffered network cancellations. He was ultimately labeled a “failure-prone actor” and a “show killer” in an article published in Newsweek.
Cryer would later recall this tough part of his career in a 2015 interview with CBS Sunday Morning. He revealed, “After the show killer thing, I joke about it now, but at the time it was a real issue for me in the industry. There were not a lot of people that wanted to hire me for a while. I spent three years, you know, with very little work.”
In fact, it’s been rumored that Cryer’s reputation as a “failure-prone actor” almost ruined his chances of getting a role in Two and a Half Men. He had hoped to get an audition for the sitcom. But it’s believed that the disgraced former CBS president Les Moonves was reluctant to have Cryer on the show because of his track record.
Nevertheless, it seems that Moonves was at least willing to give Cryer an audition, and the rest — of course — is history. The actor won the role of the uptight divorcee Alan Harper. Cryer’s character moves in with his hedonistic brother Charlie Harper, played by Charlie Sheen, following the breakdown of his marriage, alongside his son Jake (Angus T. Jones).
Unlike many of Cryer’s previous shows, Two and a Half Men was an instant hit. As the success of the sitcom grew, it became one of the highest-rated TV comedies. And some would argue that the series’ reputation hinged on the considerable talents of its cast.
Commenting on the success of Two and a Half Men in a 2007 interview with Associated Press, Cryer said, “I’ve had shows get off the launching pad and then literally explode in midair. But now I’ve finally hit the jackpot. I’m on this show that people love, working with people I love to work with.”
But the good times were not to last on Two and a Half Men. Eventually, Sheen’s tumultuous personal life started taking a toll on the show. In 2005 the actor’s second wife, Denise Richards, filed for divorce claiming he was abusing alcohol and drugs. And it was the breakdown of this relationship that Cryer believed marked the start of Sheen’s downfall.
Around the same time as Sheen’s divorce from Richards, escort and porn actress Chloe Jones claimed in an interview with the National Enquirer that the actor was one of her clients and that the pair had been intimate. Sheen’s people responded by denying Jones’ claims. However, there was yet more scandal to come.
In 2006 Sheen’s ex-wife Denise Richards filed for a restraining order against him. Richards claimed that Sheen had pushed her while she had her daughter Lola in her arms. According to a declaration, Richards signed as part of her complaint, Sheen had also pointed to her and yelled, “I hope you f****** die, b****.”
Following his divorce from Richards, Sheen married his third wife, actress Brooke Mueller, in 2008. However, less than a year into their marriage, Sheen was arrested as a result of an alleged altercation with Mueller. They ultimately divorced in 2011 and Sheen later became engaged to the former porn star Brett Rossi in 2014, though they would also part ways.
Prior to his split with Mueller, Sheen had continued his battle with alcohol and drug abuse. In February 2010 he took time off from Two and a Half Men and voluntarily checked into rehab. However, in May of that year, he sealed a two-year deal with the show, which saw him receive $1.8 million per episode.
Sheen’s downward spiral continued throughout 2010. In October he was arrested again after reportedly causing $7,000 worth of damage to a room at The Plaza Hotel in New York City in an apparent drug and alcohol-fuelled rampage. Then, at the start of the following year, Sheen entered rehab once more after being admitted to the hospital with severe pains in his abdomen.
With Sheen in rehab, the production of Two and a Half Men was put on hold. However, the unstable star was about to sever all ties he had with the hit show after publically attacking its co-creator and producer, Chuck Lorre. Warner Brothers subsequently banned Sheen from the Two and a Half Men set, and production was halted for the remainder of the series.
As the media circus surrounding Sheen intensified he continued to make a number of outlandish statements to the press. He refused requests from his employers to enter rehab and even offered urine and blood samples in order to prove he was drug-free. But in the end, Warner Brothers decided that enough was enough.
In a statement for 2007 the studio said, “After careful consideration, Warner Brothers Television has terminated Charlie Sheen’s services on Two and a Half Men, effective immediately.” At the time, Sheen had been contracted to the studio until the end of 2012. But following Sheen’s meltdown, the future of the sitcom now hung in the balance.
Given the fact no one knew what would happen to Two and a Half Men following Sheen’s dismissal, his co-stars must have been worried about the effect the situation would have on their careers. And it seems that Cryer, at least, was concerned that his future was partly in Sheen’s hands.
In April 2020 Cryer appeared on an episode of the Entertainment Weekly YouTube series Couch Surfing. During his interview, he recalled the “crazy” time surrounding Sheen’s dismissal from Two and a Half Men. Cryer said, “All of our jobs are tied into this guy, and we’re all his friends.”
Looking back at the media circus that followed Sheen at that time, Cryer commented, “It was one of the first internet s****storms.” He added, “It was very, very strange and [there were] aspects of it that I absolutely hated, but you know, I’m thankful for the years that were great.”
It seems that there’s no bad blood between Cryer and his former co-star, despite the fact that Sheen called him “turncoat, a traitor, a troll” in the wake of his firing from Two and a Half Men. Cryer told CBS Sunday Morning that, although Sheen’s comments “hurt at the time,” he’d since made peace with the troubled star.
In Cryer’s 2015 memoir, So That Happened he recalled how Sheen had been a “pretty grounded, sober married guy” when filming of Two and a Half Men begun. However, he described how he watched on as Sheen subsequently slipped into his well-publicised downward spiral. Cryer claimed that he was eager to help his co-star but was cautious about condoning some of his actions.
Cryer’s overriding concern was for the welfare of his co-star and friend, Sheen. He told CBS Sunday Morning, “I was just scared every day that I was going to read about Charlie being dead.” The actor added, “Anybody who’s gotten close to him knows that there’s a really good guy in there.”
So, even though the pair’s relationship hasn’t always been plain sailing, Cryer had nothing but kind things to say about Sheen during his appearance on Couch Surfing. During the show, Cryer spoke candidly about Sheen and revealed what it was really like working with his troubled co-star.
To begin with, though, Cryer was asked if he’d been surprised by the success of Two and a Half Men. And he admitted that he had been. The actor said, “I was. We had a lot of things going for us.” One of those things, Cryer believed, was the relationship between himself and Sheen.
Cryer revealed that he and Sheen had struck up a bond on the set of Two and a Half Men. He revealed, “Charlie and I really hit it off. We had a great first few years on that show. It was incredibly smooth, we had a lovely time, it was working really well.” However, things changed.
During his chat on the YouTube special, Cryer assumed that Sheen had started using drugs again following his split from Richards. And that it was this that ultimately led to his downfall. Cryer explained, “He was very proud of his sobriety, but then after his marriage to Denise Richards collapsed, I think he started using again.”
Cryer went on to say that Sheen initially kept his substance abuse in check, and was able to work as normal. But eventually, it caught up with him. Cryer said of his co-star, “At first he could handle it, and he was still incredibly professional — and still lovely, by the way, to everybody on set — but you could just see that stuff was wearing on him.”
Following Sheen’s dismissal from Two and a Half Men his character was killed off and Ashton Kutcher replaced the actor as the show’s new leading man. He starred as Walden Schmidt, an internet millionaire who set up home with Cryer’s character Alan Harper and his son Jake.
Cryer would go on to star in another four seasons of Two and a Half Men alongside Kutcher. However, the show eventually came to an end in 2015 after 12 seasons. Since then Cryer has gone on to guest star in shows like Will & Grace, NCIS and Robot Chicken. Most notably, he’s also played Lex Luthor on Supergirl.
Cryer’s former co-star Sheen, meanwhile, continued to experience ups and downs in both his professional and personal lives. In September 2011 he delivered a number of public apologies stating that he’d been out of control in the months surrounding his dismissal from Two and a Half Men. He subsequently took up the lead role in the FX comedy Anger Management in 2012.
Sheen’s stint on Anger Management lasted for just two years, coming to an end in late 2014. That was the actor’s last major gig, as Sheen has stayed mostly under the radar since confirming he was H.I.V. positive in 2015. He had been diagnosed with the illness four years previously and confirmed he was managing the disease with medication.
According to reports, Sheen ran into money troubles in 2018 after allegedly clocking up almost $5 million worth of debt in unpaid taxes. As a result, he requested that his child-support payments to his ex-wives Richards and Mueller stating that he’d “been unable to find steady work, and [has] been blacklisted from many aspects of the entertainment industry.”
Whether Sheen will ever replicate the success he enjoyed on Two and a Half Men remains to be seen. But in his interview with CBS Sunday Morning Cryer refused to rule out reuniting with his former co-star. He said, “We’ll see, but I’ll never say never.”