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

Jon Cryer Reveals Frustrations About “Complicated” Relationship With Charlie Sheen in New Docuseries

Jon Cryer is sharing more about his complex history with Charlie Sheen, whom he worked with for many years and knew different 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 Why He Supported Charlie Sheen’s Documentary

Jon Cryer has shed light on his decision to support Charlie Sheen’s Netflix documentary by saying that he has come to a different understanding of their relationship in the past.

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 Consider a Face-to-Face Talk with Charlie Sheen

Jon Cryer has revealed that he would consider a face-to-face meeting with Charlie Sheen, despite rumors of the two former costars feuding. “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.’ But no, they didn’t shut me down, instead they came forward.”

The film reveals Charlie Sheen’s personality and his professional life, as well as the people who influenced him.

Charlie Sheen came a very long way from being a sitcom star

The son of Martin Sheen and brother of Emilio Estevez, Charlie Sheen became a household name after playing Charlie Harper on Two and a Half Men, where he starred along with Jon Cryer for eight seasons. However, his stint on the hit CBS sitcom ended very suddenly in 2011 when he became embroiled in a very public drug addiction battle and had a flying out with the show’s creator Chuck Lorre which resulted in his dismissal.

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: From Sitcom Star to Career Evolution

Jon Cryer’s role as Alan Harper in Two and a Half Men lasted for 12 seasons and he earned two Emmy Awards for his character, the neurotic brother of Charlie, who was a divorced man. After the show ended, he wrote a memoir in 2015 and appeared on a few TV shows such as NCIS, The Ranch, and Mom.

Recently, Cryer is known for a variety of roles. Most importantly, he was the villain Lex Luthor in Supergirl from 2019 to 2021. He was also one of the lead actors playing Jim Kearney in the sitcom Extended Family that was broadcasted from 2023 to 2024. As far as his private life is concerned, he has a daughter named Daisy whom he shares with his wife Lisa Joyner and a son, Charlie, from his previous marriage to Sarah Trigger.

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

Angus T. Jones first became famous as the young “half man” Jake Harper on the TV show Two and a Half Men and by the age of 17 was one of the highest-paid child actors on television. However, in 2013 he left the popular sitcom after deciding to live a more faith- based life and only came back briefly for the series finale 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

Ashton Kutcher entered the cast of Two and a Half Men at the start of season nine after Charlie Sheen’s exit. 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.

Regarding his personal life, Kutcher tied the knot with his That ’70s Show co-star Mila Kunis shortly after Two and a Half Men ended. The couple has two children, a daughter Wyatt and a son Dimitri.

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 also landed roles on TV shows The Affair, Red Band Society, Madam Secretary, Homeland and Speechless.

Her performance as Rose Weissman in The Marvelous Mrs. Maisel from 2017 to 2023 earned Marin Hinkle a lot of praise.

On the personal front, she has a son with her ex-husband Randall Sommer. His name is Ben.

Melanie Lynskey: A Journey from a ‘Two and a Half Men’ Rose to a Critically Acclaimed Actor

Initially a fan favorite on Two and a Half Men for her portrayal of Rose, the eccentric and unpredictable neighbor of the Harpers, Melanie Lynskey’s character had a twisted 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.

Outside of the sitcom, Lynskey has made a name for herself as a talented and versatile actress in film and television. Her movies include Sadie, Little Boxes, The Changeover and Pike River, while she has also been lauded for her performances in TV shows like Togetherness, Castle Rock, Mrs. America, Candy and Yellowjackets.

On the personal front, Lynskey had a baby girl with actor Jason Ritter in 2018, and the two tied the knot in 2020.

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

Amber Tamblyn stepped into Two and a Half Men as Charlie Harper’s long-lost illegitimate daughter, Jenny, in the last two seasons of the show. Her character helped to revitalize the sitcom in its last 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. She also chose to go a step further by directing and co-writing the film Paint It Black released in 2016.

On a different note, Amber Tamblyn said “I do” to actor and comedian David Cross in 2012 and, five years later, they became parents of a baby girl, Marlow.