Jon Cryer Details “Complicated Relationship” With Charlie Sheen

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

Jon Cryer, who worked with Charlie Sheen on Two and a Half Men for eight seasons, has spoken about participating in Charlie Sheen’s upcoming 2025 Netflix documentary, aka Charlie Sheen, even though they had a difficult relationship.

Jon described his experience as ‘interesting’ during an appearance on The View in May. He admitted to having conflicted emotions about participating, explaining that he and the person involved had a complex relationship.

In 2011, Charlie was let go from their show after his struggles with addiction became public. Recently, Jon explained why he still feels upset with how the media covered his colleague during that challenging period.

The actor from Pretty in Pink explained that he’d mostly moved past being angry with the documentary’s subject. He was still upset with how America reacted, though, because many people seemed to delight in the subject’s downfall when he started behaving erratically.

Knowing him both as a friend and colleague made it really upsetting to witness everything that happened and see people seemingly enjoying it. That’s a big reason why I felt it was important to share my perspective.

Jon mentioned that Charlie was grateful for his help with the documentary. Charlie even texted him a simple ‘Thanks for doing it.’

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

“Yes, I would,” he said. “It’s strange, because sometimes you’ll see articles claiming we’re fighting, but that’s just not true.”

Jon made these statements a week after Charlie, age 60, shared that he hadn’t spoken to the Supergirl actor since they both appeared in the two-part Netflix documentary.

The actor told People magazine that he hates bothering others, which is why he’d often tell reporters he would contact Jon Cryer, even though he never actually did, in an interview published on April 24th.

He added that he believed Jon would likely be receptive to the idea, describing him as a kind and skilled person.

He also expressed his appreciation for Jon’s involvement in the documentary, which featured in-depth stories about his life told by his family, friends, former partners, and colleagues.

Charlie recently explained that he was really touched by the support everyone showed for the project. He acknowledged that people could have easily refused to participate, saying they’d already experienced it and didn’t want to revisit it, and he would have understood. However, he was grateful they chose to get involved and offer their support instead.

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

Charlie Sheen, son of Martin Sheen and brother of Emilio Estevez, starred as Charlie Harper in the first eight seasons of the hit CBS sitcom Two and a Half Men, alongside Jon Cryer. The show’s eighth season was cut short in 2011 due to Sheen’s struggles with addiction.

He famously had public disagreements with the show’s executive producer, Chuck Lorre, which led to his firing and the creation of catchphrases like “winning” and “tiger blood.” His character was written off the show and later appeared as a ghost played by Kathy Bates.

After leaving Two and a Half Men, Sheen went on to star in the television adaptation of Anger Management, which ran from 2012 to 2014. More recently, he’s made appearances on The Goldbergs and in the films Scary Movie 5, Machete Kills, and 9/11.

In 2023, Charlie Sheen, who publicly shared his HIV diagnosis in 2015, made a brief appearance as himself on the Max series Bookies. He followed this with the release of his memoir, The Book of Sheen, and a two-part documentary called aka Charlie Sheen in 2025.

Sheen has been sober since late 2017. He has five children: sons Bob and Max with his ex-wife Brooke Mueller, daughters Sami and Lola with ex-wife Denise Richards, and a daughter, Cassandra Estevez, from a previous relationship.

Jon Cryer is best known for playing Alan Harper on all twelve seasons of Two and a Half Men. Since then, he’s appeared in several other shows, including Mom, The Ranch, NCIS, Robot Chicken, and Lady Dynamite. He also took on the role of Lex Luthor in Supergirl (2019-2021) and Jim Kearney in Extended Family (2023-2024).

Cryer has two children: daughter Daisy with wife Lisa Joyner, and son Charlie with ex-wife Sarah Trigger.

Despite participating in the Netflix documentary aka Charlie Sheen, Cryer revealed he and Charlie Sheen are no longer close. In a January 2025 interview on Club Random With Bill Maher, Cryer stated, “We don’t have a relationship anymore.” He added that he wishes Sheen well and is happy to hear about his sobriety, sharing they still have some friends in common.

Angus T. Jones is best known for playing Jake Harper on the TV show Two and a Half Men, the son of Alan Harper. He became the highest-paid teenage actor on television, but he left the show in 2013 after becoming deeply religious. He did, however, make a final appearance in the show’s last episode in 2015.

After leaving the sitcom, Jones went to the University of Colorado Boulder and later started a media and events company with Justin Combs, the son of Sean Combs.

In 2023, he made a brief appearance as himself on the Max series Bookies.

Jones generally keeps a low profile, but in 2020, he announced on Instagram that he was pursuing a career in music, saying, “I do music now, go head and get used to it loves.”

Ashton Kutcher, known for his role in That ’70s Show, joined Two and a Half Men in its ninth season after Charlie Sheen left the show. He stayed with the series until it ended in 2015, playing Walter Schmidt, a wealthy man who bought the house after Charlie Harper’s character died.

Following the end of Two and a Half Men, Ashton Kutcher starred in shows like The Ranch and films such as Vengeance and Your Place or Mine. Beyond acting, he’s a successful venture capitalist with investments in companies like Airbnb and Uber.

Kutcher married his That ’70s Show co-star, Mila Kunis, a few months after the series concluded in July 2015. They have two children together: a daughter named Wyatt and a son named Dimitri.

Conchata Ferrell often appeared in memorable supporting roles in films and TV shows like Erin Brockovich, Network, L.A. Law, and E/R (a different show than ER). She became widely known for her role as the funny and outspoken housekeeper, Berta, on Two and a Half Men, which earned her two Emmy nominations.

Following the conclusion of Men, Ferrell acted in Krampus and Grace and Frankie, and later worked with Kutcher again on The Ranch. She passed away in October 2020 at the age of 77.

Oh my gosh, Marin Hinkle is amazing! I totally knew her from ‘Two and a Half Men’ as Alan’s ex, Judith, but she’s been everywhere since then! I was so excited to see her in ‘Jumanji: Welcome to the Jungle’ in theaters, and she’s popped up in so many great shows – ‘The Affair,’ ‘Red Band Society,’ ‘Madam Secretary,’ ‘Homeland,’ and even ‘Speechless’! But honestly, her role as Rose Weissman in ‘The Marvelous Mrs. Maisel’ is just perfection. I was obsessed with that show from 2017 to 2023, and she was a huge part of why! I also read she has a son, Ben, with her ex-husband, Randall Sommer. She’s just incredible, I could talk about her forever!

Melanie Lynskey is recognizable to viewers of Two and a Half Men as Rose, the somewhat quirky neighbor of the Harpers. Her character had a relationship with Charlie and initially told everyone he had passed away in season nine. However, the show’s finale revealed that she had actually been holding him captive for four years.

Melanie Lynskey is a well-known actress who has appeared in films like Sadie, Little Boxes, The Changeover, and Pike River. She’s also starred in TV series including Togetherness, Castle Rock, Mrs. America, Candy, and Yellowjackets. In 2018, she and Jason Ritter had a daughter, and they got married in 2020.

Amber Tamblyn played Jenny, Charlie’s previously unknown daughter, on seasons 11 and 12 of the show. Since finishing her work on Two and a Half Men, she’s been in films like You Hurt My Feelings, Y: The Last Man, Nostalgia, and Girlfriend’s Day. She also wrote and directed the 2016 movie Paint It Black. Tamblyn married David Cross in 2012, and they have a daughter named Marlow, born in 2017.

Holland Taylor is well known for her role as Evelyn Harper on all twelve seasons of Two and a Half Men. Since then, she’s appeared in popular TV series like The Morning Show, The Chair, Hollywood, and Mr. Mercedes. She’s also added several films to her resume, including 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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2026-05-02 22:18