Why Charlie Sheen Hasn’t Reached Out to Two & a Half Men’s Jon Cryer

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Charlie Sheen and Jon Cryer don’t exactly have a winning relationship these days.

Even though both Charlie Sheen and Jon Cryer appear in the 2025 documentary aka Charlie Sheen, Sheen says they haven’t spoken since it came out.

You know, I’m a pretty private person, and I really dislike imposing on others. I recently shared with People magazine that I’ve often told reporters I’d connect with Jon Cryer, but honestly, I just never get around to actually doing it. It’s just my way of politely letting people know without making a firm commitment I might not keep.

The speaker, who is 60 years old, added that Jon would likely be receptive to the idea. They described him as a kind and gifted person.

He’s still thankful that Jon Cryer, age 61, participated in his documentary. The film features in-depth stories about Sheen’s life, shared by his family, friends, former partners, and colleagues from past shows.

Honestly, it just meant the world to me that everyone involved actually wanted to revisit this stuff. I kept thinking, they could have totally just said, ‘No way, I’m done with this,’ and I would have completely understood! I’d have been like, ‘Okay, fair enough.’ But they didn’t! They really showed up, and it just… it meant everything that they were willing to talk about it again. It was amazing.

During the same discussion, the former Spin City cast member jokingly admitted that his relationship with Cryer has been somewhat strained.

He addressed the crowd, saying, “Jon isn’t here tonight, is he?” Then, expressing his confusion and eventual acceptance, he continued, “I was shocked, but I’ve moved past it. I’m just wondering what’s going on with Jon.”

After eight seasons on Two and a Half Men, Charlie Sheen was fired in 2011, and Jon Cryer ended their working relationship. Sheen publicly criticized Cryer, calling him a “turncoat,” “traitor,” and “troll” for not offering support during his struggles with addiction.

As a huge fan, it was so strange when Charlie Sheen left! But the show really persevered. Angus T. Jones, thankfully, stayed on, and they brought in Ashton Kutcher, which helped them keep going for three more seasons. It wasn’t the same, of course, but I was glad they didn’t just cancel it!

When Charlie Sheen was fired, my publicist asked if I wanted to release a statement since we were close. I had actually started writing one – something about how great it had been working with him – when my publicist suddenly interrupted. She told me Sheen had just publicly called me a traitor, a turncoat, and a troll. So, I decided to hold off on releasing that nice statement.

And while Sheen eventually got sober, he and Jon did not reconcile.

In a 2025 appearance on Club Random With Bill Maher, Jon Cryer revealed that he and Charlie Sheen are no longer in contact. He expressed well wishes for Sheen and mentioned they still have friends in common. Cryer also shared he’s happy to hear Sheen has been sober for some time.

As for the rest of the Two and a Half Men cast? Keep reading to find out where they are today.

Charlie Sheen, son of Martin Sheen and brother of Emilio Estevez, starred as Charlie Harper on the CBS sitcom Two and a Half Men for its first eight seasons, alongside Jon Cryer. In 2011, his struggles with addiction led to his departure from the show after a public conflict with executive producer Chuck Lorre. This resulted in his character being written off the series, with a brief appearance as a ghost played by Kathy Bates.

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

Charlie Sheen appeared as himself in a cameo role on the Max series Bookies in 2023. 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 publicly revealed his HIV-positive status in 2015 and has been sober since late 2017. He has five children: sons Bob and Max with ex-wife Brooke Mueller, daughters Sami and Lola with ex-wife Denise Richards, and a daughter, Cassandra Estevez, from a previous relationship.

As a lifestyle expert, I’ve always admired Jon Cryer’s versatility! Most people remember him as Alan Harper on Two and a Half Men, and he really carried that show for all twelve seasons. But what a lot of people don’t realize is how consistently he’s worked since then! He’s popped up in everything from comedies like Mom and The Ranch to even Robot Chicken and Lady Dynamite. More recently, he’s had some fantastic roles playing Lex Luthor on Supergirl and Jim Kearney on Extended Family.

On a personal note, Jon’s a family man – he and his wife, Lisa Joyner, have a daughter, Daisy, and he also has a son, Charlie, with his ex-wife, Sarah Trigger.

It’s interesting to hear about his relationship with Charlie Sheen, too. While he participated in the Netflix documentary aka Charlie Sheen, they aren’t close anymore. He’s said they don’t really have a relationship now, but he genuinely wishes Charlie well and is happy to hear he’s doing better and staying sober. It’s a testament to Jon’s character that he can maintain that positive outlook even with past complexities.

Angus T. Jones is best known for playing Jake Harper on the TV show Two and a Half Men, becoming the highest-paid child actor on television at age 17. He left the show in 2013 after becoming deeply religious, though he did appear in the series finale 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 largely stays out of the public eye, but shared on Instagram in 2020 that he’s now focused on making music.

Ashton Kutcher, known for his role in That ’70s Show, became part of Two and a Half Men starting with season nine. He joined the show after Charlie Sheen left and remained until the series ended in 2015. Kutcher played Walter Schmidt, a wealthy man who bought the house previously owned by the character Charlie Harper after 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. He’s also 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 show ended in July 2015. They have two children: a daughter named Wyatt and a son named Dimitri.

Conchata Ferrell often appeared in memorable supporting roles in television and film, including appearances in Erin Brockovich, Network, L.A. Law, and E/R (a show separate from ER). She became widely known for her role as the sarcastic 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.

Following the conclusion of her role as Judith on the CBS sitcom, Marin Hinkle appeared in the film Jumanji: Welcome to the Jungle. She also had roles in several TV series, including The Affair, Red Band Society, Madam Secretary, Homeland, and Speechless. From 2017 to 2023, she played Rose Weissman on The Marvelous Mrs. Maisel. Hinkle and her ex-husband, Randall Sommer, have a son named Ben.

Melanie Lynskey is remembered by viewers of Two and a Half Men for her role as Rose, the quirky neighbor of the Harpers. Her character initially told everyone Charlie had passed away in season nine, but the series finale shockingly revealed she’d actually been holding him captive for four years.

Melanie Lynskey is an accomplished actress, well-known for her work in films such as Sadie, Little Boxes, The Changeover, and Pike River. She’s also appeared in popular TV series including Togetherness, Castle Rock, Mrs. America, Candy, and Yellowjackets. In 2018, she and Jason Ritter welcomed their daughter, and they married in 2020.

Amber Tamblyn played Jenny, Charlie’s previously unknown daughter, during seasons 11 and 12 of the show. Since then, she’s been in several projects including the films You Hurt My Feelings, Y: The Last Man, Nostalgia, and Girlfriend’s Day. She also wrote and directed the 2016 film 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, the mother of Alan and Charlie. Since then, she’s appeared in several other popular TV series, including The Morning Show, The Chair, Hollywood, and Mr. Mercedes. She’s also added several films to her resume, such as 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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2026-04-24 23:50