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    Jon Cryer Details “Complicated Relationship” With Charlie Sheen

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    Watch: Jon Cryer Details “Complicated Relationship” With Charlie Sheen

    Jon Cryer is sharing two and a half truths about his relationship with Charlie Sheen. 

    The Two and a Half Men actor—who costarred alongside Charlie on the hit series for eight seasons—shared insight into being a part of The Three Musketeers star’s 2025 Netflix docuseries aka Charlie Sheen, despite their tumultuous relationship. 

    “It was interesting,” Jon said during his May 1 appearance on The View. “I had a lot of mixed feelings about being a part of it because obviously he’s a very complicated guy and we had a complicated relationship.”

    Charlie was terminated from the pair’s show in 2011 following his publicized battle with addiction. Looking back, Jon shared why he still takes issue with how the media portrayed his costar during the difficult time. 

    “Mostly I realized that I wasn’t mad at him anymore; I was still kind of mad at America,” the Pretty in Pink actor explained of his decision to take part in Charlie’s documentary. “Because when he went off the rails and went crazy, a lot of people seemed to enjoy that.” 

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    “I knew him as a friend, as a coworker, and so it was really painful to see all that and see that craziness and see a lot of people enjoying it,” the 61-year-old added. “So that’s part of why I kind of wanted to, obviously, say my side of the story.”

    Jon also noted that Charlie appreciated his involvement in the doc, adding that the Young Guns actor sent him a text saying, “Thanks for doing it.” 

    Photo by Kevin Winter/Getty Images for PCA

    As for whether Jon would be open to chatting face-to-face with Charlie in the future?

    “Yeah, I would,” he explained. “I mean, it’s funny because every now and then an article comes out that we’re arguing and it’s just not the case.”

    Jon’s comments come one week after Charlie, 60, revealed that he and the Supergirl actor had not connected since appearing on the two-episode Netflix doc.  

    “I don’t like to bother people,” the actor admitted to People in an interview published April 24, explaining how he would tell reporters that he’d reach out to Cryer but “never” does.

    Photo by Greg Gayne/CBS via Getty Images

    “But I think Jon would be open to that,” he continued. “Jon’s a lovely man and a very talented guy.”

    Still, he shared how grateful he was to have Jon in the documentary, which included detailed accounts about Sheen’s life from his family, friends, exes and former castmates.

    “It was very sweet, very cool that everybody showed up like they did, because they could have easily said, ‘Go f–k yourself. I’m not interested. I lived it. I don’t need to talk about it again,'” Charlie shared during a recent panel discussion about the project, per People. “And I would have been, ‘OK, that’s fine.’ But they didn’t, and they stepped up.”

    Keep reading to find out where the Two and a Half Men cast is today…

    Robert Voets/CBS via Getty Images, Charley Gallay/Getty Images for Project Angel Food

    Charlie SheenCharlie Sheen—the son of Martin Sheen and brother to Emilio Estevez—was one of the original “men” in Two and a Half Men, playing Charlie Harper in the first eight seasons of the CBS sitcom opposite on-screen brother Jon Cryer. The eighth season was cut short in 2011 amid Sheen’s battle with addiction.He famously clashed with executive producer Chuck Lorre in the press and social media, resulting in his dismissal from the series (and the coinage of phrases like “winning” and “tiger blood”). His character was killed off and later played as a ghost by Kathy Bates.After exiting Two and a Half Men, Sheen booked the TV version of Anger Management, which aired from 2012 to 2014. Since, he popped up on The Goldbergs and on the big screen in Scary Movie 5, Machete Kills and 9/11.In 2023, the actor—who shared in 2015 he is HIV-positive—made a cameo as himself on Lorre’s Max series Bookies. He released his memoir The Book of Sheen as well as the two-part documentary aka Charlie Sheen in 2025.Sheen, who revealed in 2015 that he is HIV-positive, has been sober since late 2017. He shares sons Bob Sheen and Max Sheen with ex-wife Brooke Mueller, daughters Sami Sheen and Lola Sheen with ex-wife Denise Richards and daughter Cassandra Estevez from a previous relationship.

    Sonja Flemming/CBS via Getty Images, Michael Tran/FilmMagic

    Jon CryerCryer starred in all 12 seasons of Two and a Half Men as Charlie’s divorcee brother Alan Harper.After the show, Cryer released a 2015 memoir and popped up on shows like Mom, The Ranch, NCIS, Robot Chicken and Lady Dynamite. Cryer then went on to play Lex Luthor on the TV series Supergirl from 2019 to 2021 as well as Jim Kearney on Extended Family, which ran from 2023 to 2024.Cryer shares daughter Daisy with wife Lisa Joyner as well as son Charlie with ex-wife Sarah Trigger.Though Cryer agreed to sit down for Netflix’s aka Charlie Sheen, the two aren’t exactly friends. “We don’t have a relationship anymore,” Cryer said on a January 2025 episode of Club Random With Bill Maher. “I wish him the best. We have some mutual friends still, and I’ve heard he’s been sober for a while, which is great to hear.”

    Chuck Lorre Prod/Kobal/Shutterstock, Desiree Stone/Getty Images

    Angus T. JonesAngus T. Jones played the “half man” in Two and a Half Men, starring as Jake, Alan Harper’s son. He became the highest paid child actor on TV at age 17, but then left the series in 2013 after forging down a religious path. However, he did return for the series finale in 2015.Jones attended University of Colorado Boulder after leaving the sitcom and, at one point, teamed up with Sean Combs‘ son Justin Combs for a media and events company.In 2023, he made a cameo as himself on Lorre’s Max series Bookies. Jones continues to lead a life out of the spotlight, but noted in a 2020 Instagram post, “I do music now, go head and get used to it loves.”

    Cliff Lipson/CBS via Getty Images, Alberto E. Rodriguez/Getty Images

    Ashton KutcherThat 70s Show alum Ashton Kutcher joined Two and a Half Men in season nine after Sheen’s infamous exit and stayed through the end of the series in 2015. He played billionaire Walter Schmidt, who purchased Charlie Harper’s house following the character’s death.After Two and a Half Men wrapped, Kutcher appeared on shows like The Ranch as well as in movies like Vengeance and Your Place or Mine. He’s also a venture capitalist, having invested in companies like Airbnb and Uber. Kutcher married his costar from That ’70s Show Mila Kunis months after the series wrapped in July 2015. The married duo are parents to daughter Wyatt and son Dimitri.

    Cliff Lipson/CBS via Getty Images; Walter McBride/FilmMagic

    Conchata FerrellConchata Ferrell popped up in supporting roles throughout her career, including Erin Brockovich, Network, L.A. Law and E/R (not to be confused with ER). As wisecracking housekeeper Berta on Two and a Half Men, she received two Emmy nominations.After Men ended, Ferrell appeared in Krampus, Grace and Frankie and reunited with Kutcher on The Ranch. She died in October 2020 at 77 years old. 

    Cliff Lipson/CBS Photo Archive via Getty Images, Jon Kopaloff/Getty Images

    Marin HinkleAfter the CBS sitcom ended, Marin Hinkle—who played Alan’s ex-wife Judith— appeared in Jumanji: Welcome to the Jungle on the big screen, and as part of The Affair, Red Band Society, Madam Secretary, Homeland and Speechless on the small. She then landed the role of Rose Weissman on The Marvelous Mrs. Maisel, which ran from 2017 to 2023. Hinkle shares son Ben with her ex-husband Randall Sommer.

    Monty Brinton/CBS via Getty Images; Randy Shropshire/Deadline via Getty Images

    Melanie LynskeyMelanie Lynskey is best known to Two and a Half Men fans as Rose, the Harper’s kinda strange next-door neighbor. After having a relationship with Charlie, she claimed in season nine that he had died. But in the series finale, it was revealed she kept him prisoner for four years.Lynskey is known for her roles in films like Sadie, Little Boxes, The Changeover and Pike River, plus her TV performances in shows like Togetherness, Castle Rock, Mrs. America, Candy and Yellowjackets. Lynskey welcomed a daughter with Jason Ritter in 2018, and the couple wed two years later.

    Monty Brinton/CBS via Getty Images; Jamie McCarthy/Getty Images for Tribeca Festival

    Amber TamblynAmber Tamblyn joined the cast for seasons 11 and 12 as Jenny, Charlie’s long-lost illegitimate daughter.Since the end of Two and a Half Men, the Sisterhood of the Traveling Pants alum has appeared in You Hurt My Feelings, Y: The Last Man, Nostalgia, and Girlfriend’s Day. She also directed and co-wrote the 2016 film Paint It Black.Tamblyn wed David Cross in 2012 and they welcomed daughter Marlow five years later.

    Sonja Flemming/CBS via Getty Images; Roy Rochlin/Getty Images for Literacy Partners

    Holland TaylorHolland Taylor starred in all 12 seasons of Two and a Half Men as Evelyn, Alan and Charlie’s mother.Afterwards, The Practice alum appeared in several more TV shows, including The Morning Show, The Chair, Hollywood, and Mr. Mercedes. Her list of film credits has also grown to include Motherland, Quiz Lady, The Stand In, Bombshell and Gloria Bell.Taylor has been in a relationship with Sarah Paulson since 2015.

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