Jon Cryer Talks about His “Complicated Relationship” With Charlie Sheen

Jon Cryer Opens Up About His ‘Complicated’ Relationship With Charlie Sheen in New Docuseries

Jon Cryer is talking about his complicated relationship with Charlie Sheen who he had worked with for many years and knew various sides of.

On The View, May 1, the Two and a Half Men actor talked about the reasons he said yes to be one of the talking heads in the 2025 Netflix documentary featuring Sheen, aka Charlie Sheen.

Thinking about the offer Cryer said he had a very hard time deciding. “I was very confused, ” he revealed to the hosts. “There were lots of reasons why I wasn’t sure about doing it because, of course, he’s a very complicated guy and our relationship was complicated as well.”

The pair were shooting the TV show for eight seasons when Sheen got a pink slip in 2011 after publicly battling drugs. Recalling that time, Cryer shared some of his thoughts on how the press handled Sheen’s addiction and, in fact, he still has a problem with how his scene partner was shown during one of the most difficult periods in his life.

Jon Cryer Explains Reason Behind Supporting Charlie Sheen’s Documentary

Jon Cryer has revealed why he decided to back Charlie Sheen’s Netflix documentary is because he has come to understand their relationship differently recently.

The main thing that still upset Cryer was not Sheen himself, but the way the public reacted to his personal issues.

“What I realized is, I was no longer angry with him; I was still having some anger towards America, ” Cryer said. He shared that he was deeply sad that so many people seemed to enjoy Sheen’s public degradation back then. On top of the friendship and work relationship side, Cryer was quite hurt to see the “madness” and the public’s enjoyment of it, which prompted him to tell his side of the story.

Sheen is grateful to Cryer for this help. He told that the actor from Young Guns knocked on his door in a friendly way by sending him a text, “Thanks for doing it.”

Jon Cryer Would Be Willing to Meet Charlie Sheen

Following reports that the two former co-stars are on bad terms, Jon Cryer has suggested that he could be open to meeting Charlie Sheen face-to-face.

“Yeah, I would, ” he said, denying reports of them having renewed arguments as false. “Every now and then an article comes out that we’re arguing and it’s just not the case.”

Comments from Jon Cryer came in the wake of an interview given by Sheen only a week earlier. During the interview, the 60-year-old actor revealed that the duo hasn’t actually talked following their appearance in the Netflix docuseries.

Charlie Sheen said he often tells the media that he plans to get in touch with Cryer but hardly ever does it. “I don’t like to bother people, ” Sheen revealed, explaining that his not communicating with Cryer isn’t because of hostility but a personal preference of not wanting to impose on others.

Charlie Sheen Lifts Up Jon Cryer

Charlie Sheen has lavished praise on Jon Cryer, believed that his ex-Two and a Half Men co-star would probably be interested in getting back together someday. “Jon would be quite open to that, I think, ” the actor expressed, “and without a doubt, Jon is a wonderful man and a very talented guy.”

Besides, Charlie Sheen revealed how much he values Jon Cryer’s contribution to the Netflix documentary about his life in which the main inspiration is the testimonies of his family, friends and former colleagues.

The actor further acknowledged that he was moved when many people agreed to take part. “They were really sweet, it was a very nice gesture that everyone showed up as they did, ” he said at a panel, observing that they could have very well said no. “They could have replied, ‘Go f–k yourself…’ and I would have been, ‘OK, that’s fine.’ On the contrary, they didn’t close me down, they just came forward.”
On the film, we see both Charlie Sheen’s character and his professional life, as well as the people who have shaped him.

Charlie Sheen has travelled far beyond just being a sitcom star

After leaving the show, Sheen starred as the main character in the TV series Anger Management that was on air 2012 to 2014. He then made guest appearances in TV series The Goldbergs and movies like Scary Movie 5, Machete Kills and 9/11.

Nowadays, Sheen has been gradually coming back to the stage. He featured as himself in Lorre’s Max series Bookies in 2023, and in 2025, he came out with a memoir titled The Book of Sheen and also a two-part documentary called aka Charlie Sheen.

He made the big announcement about being HIV-positive in 2015, and since then he has been quite transparent about his way out of the situation. He credits his sobriety to late 2017 and he is a father of five. He has sons Bob and Max with his former wife Brooke Mueller, daughters Sami and Lola with Denise Richards, and daughter Cassandra from a past relationship.

Jon Cryer shifts beyond sitcom fame through gradual career changes

Out of nowhere, Jon Cryer stepped into the part of Alan Harper on Two and a Half Men – twelve years rolled by while he played that anxious, recently divorced guy beside his cooler brother Charlie. Recognition followed: two Emmys landed in his hands. Once the credits stopped rolling, he turned to pages instead of scripts, releasing a personal book by 2015. Small screen roles kept coming after that – spots on NCIS, then The Ranch, later showing up in Mom too.
These days, Cryer shows up in different parts on screen. Off camera, his life includes a daughter called Daisy, born during his marriage to Lisa Joyner. From an earlier time with actress Sarah Trigger, he has a son named Charlie. Although Cryer was a part of the Netflix documentary in 2025 titled Charlie Sheen, he has openly stated that Sheen and he are not friendly anymore. In an interview on Club Random With Bill Maher in early 2025, Cryer admitted they don’t have a personal relationship anymore but was very positive about Sheen’s sobriety and said, “I wish him the best.”

Angus T. Jones: The Journey of a Child Actor and His Decision to Live a Life Away from the Spotlight

Back then, fame found Angus T. Jones early – he played Jake Harper, the boy growing into manhood on Two and a Half Men. By seventeen, paychecks ranked him near the top among kid actors on TV. Then came 2013: beliefs shifted, choices changed, the show let go. A quiet exit followed, just a short return later when endings drew close in 2015.

After quitting the film industry completely, Jones went to the University of Colorado Boulder and also looked into running different types of businesses, including a media and events company with Justin Combs, son of Sean “Diddy” Combs.

He got down from the limelight for the most part but still managed to have a cameo appearance as himself on Chuck Lorre’s Max series Bookies in 2023. Even though he has been out of limelight mainly, Jones gave a creative change, for example, in a 2020 Instagram post he said “I do music now, go ahead and get used to it loves.”

Ashton Kutcher: Turning a Replacement Role into a Hollywood and Entrepreneurial Career

He was introduced as a wealthy and handsome Walden Schmidt who bought Charlie Harper’s house. Ashton Kutcher was part of the series till it went off air in 2015.

On finishing the sitcom, Kutcher kept the show going through his various television and film projects such as The Ranch, Vengeance and Your Place or Mine. Aside from acting, he has been building a venture capitalist career successfully. He has participation in major companies Airbnb, Uber etc.

Following Two and a Half Men ending, Kutcher tied the knot with Mila Kunis, his co-star on That ’70s Show. Their firstborn is a girl named Wyatt, afterward, they had a boy whom they named Dimitri.
Family life took shape quietly, away from the shows that made them known.

Conchata​‍​‌‍​‍‌​‍​‌‍​‍‌ Ferrell: Beloved ‘Two and a Half Men’ Star Laid to Rest After Her Iconic Role

Conchata Ferrell was a consummate character actor who accumulated a long list of credits, most often as a supporting player, in such productions as Erin Brockovich, Network, L.A. Law and E/R. The actress became a household name and darling of the TV audience for her portrayal of the no-nonsense housekeeper Berta in Two and a Half Men that got her two Emmy nominations.
After the series finale, Ferrell kept on working and her movie credits include Krampus and TV series Grace and Frankie, later did a reunion with Ashton Kutcher on The Ranch.
The actress died in October 2020 at the age of 77, and is remembered as one of the most compelling comedic supporting actors on ​‍​‌‍​‍‌​‍​‌‍​‍‌television.

Marin Hinkle: From Two and a Half Men to Award-Winning Roles

After Two and a Half Men finale Marin Hinkle (Alan’s ex-wife Judith) decided to keep on acting and soon became a well-known television and movie actress. She​‍​‌‍​‍‌​‍​‌‍​‍‌ was in Jumanji: Welcome to the Jungle and has been seen in TV shows like The Affair, Red Band Society, Madam Secretary, Homeland, and Speechless.
For her role of Rose Weissman in The Marvelous Mrs. Maisel, she was showered with many awards, from 2017 to 2023.
On the personal side, she has a son, Ben, with her ex-husband Randall ​‍​‌‍​‍‌​‍​‌‍​‍‌Sommer.

Melanie​‍​‌‍​‍‌​‍​‌‍​‍‌ Lynskey: A Former “Two and a Half Men” Player Turned Top Rated ​‍​‌‍​‍‌​‍​‌‍​‍‌Actress

At first, a fan favorite on Two and a Half Men because of her role as Rose, the strange and wild neighbor of the Harpers, a character that had a quite dangerous relationship with Charlie.

At one point, she even claimed he had died, but the series finale showed she had been secretly keeping him captive for several years.

Amber Tamblyn: Charlie’s Daughter on Two and a Half Men to a Multitalented Creative

Amber Tamblyn came on board the show Two and a Half Men as Charlie Harper’s daughter, Jenny, who was a long-lost illegitimate one, in the final two seasons of the series. Her role significantly contributed to the revival of the sitcom during its final years.

After the series’ end, Tamblyn did not limit herself to only films like You Hurt My Feelings, Y: The Last Man, Nostalgia and Girlfriend’s Day. What’s more, she didn’t stop at that, since she not only directed the film but also took part in writing Paint It Black released in 2016.
In a totally different direction, Amber Tamblyn married actor and comedian David Cross in 2012 and, five years later, they had a daughter, Marlow.