Where Charlie Sheen and Jon Cryer Stand 10 Years After Two and a Half Men

Watch:Charlie Sheen Shares Plea for Two and a Half Men Costar Jon Cryer

When it comes to the real story of Charlie Sheen, you probably haven’t heard half of it.

While there have been plenty of headlines about his life, the actor is telling his side in the upcoming Netflix documentary aka Charlie Sheen and including accounts from his family, friends, exes and former castmates, including his Two and a Half Men costar Jon Cryer.

“It was really cool to hear from his perspective,” Sheen recently told People. “He was in the line of fire with all that stupid s–t going on, and it was affecting him and his family and his career and all that. I can’t debate anything that he said.”

It appears he can’t get a hold of him, either. While Sheen noted he wrote to Cryer to thank him for what he shared “so honestly and very compassionately” in the doc, he didn’t hear back. 

“I’m thinking I wrote to the wrong number,” the Anger Management star added. “It’s not like Jon did not respond. He’s super responsible like that. So if you’re reading this, Jon, DM me your new number!”

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Charlie Sheen Shares Plea for Two and a Half Men Costar Jon Cryer

Then again, the two haven’t exactly stayed in contact in recent years.

“We don’t have a relationship anymore,” Cryer said on a January 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.”

Of course, their relationship wasn’t always so frayed. After Two and a Half Men premiered in 2003, they “had a great first few years on the show,” Cryer told People TV in 2020. “It was incredibly smooth. We had a lovely time. It was working really well.”

Until it wasn’t.

“He was sober when we started. He was very proud of his sobriety,” Cryer continued. “But then after his marriage to Denise Richards collapsed, I think he started using again. At first, he could handle it, and he was still incredibly professional and still lovely by the way to everybody on the set. But you could just see that stuff was wearing on him.”

E.J. Camp/CBS via Getty Images

In the years after he and Richards finalized their very public divorce in 2006, Sheen continued to make headlines, with a 2009 arrest for an incident involving now-ex wife Brooke Mueller (he pled guilty to misdemeanor assault and spent a month in rehab), his 2011 public breakdown and a continued battle with addiction.

“It was crazy because it became one of the first internet s–tstorms,” Cryer added. “And there’s all that, plus the fact that all of our jobs are tied into this guy. And we’re all his friends.”

In March 2011, Sheen was fired from Two and a Half Men, and Cryer will never forget his former castmate’s words to him.

“The day he got fired my publicist said, ‘Well, do you want to put out a public statement because you guys were so close?'” the Pretty in Pink alum said on a 2015 episode of The Meredith Vieira Show. “And I was in the midst of writing the public statement—’it’s been an honor to work with Charlie all these years’—when my publicist said, ‘Oh wait, oh wait. It’s just come over the wire. He’s called you a traitor, a turncoat and a troll.’ And I was like, ‘OK, let’s put a pin in that statement of support.'”

Greg Gayne/Warner Bros Tv/Chuck Lorre Prod/Kobal/Shutterstock

While the show continued on—with Ashton Kutcher stepping in until the series ended in 2015—Cryer and Sheen’s bond did not. 

“When you’re friends with Charlie Sheen, you have to decide how much of that you can have in your life,” the Supergirl actor told Larry King in 2014. “I wouldn’t say we’re not friends because that entails that I’m angry at him and don’t like him. It’s not that. I can’t really have him in my life.”

Although, he said they did reunite a few years later and that Sheen apologized.

“It was great to see him after all of the craziness,” Cryer told CBS Sunday Morning in 2015, “because we did have something great together.”

But for those wondering if they’d ever do something like a reboot, Cryer has his reservations.

“When Two and a Half Men was happening, Charlie was like the highest paid actor in television—probably ever,” he said on a 2024 episode of The View. “There has been nobody that has surpassed the enormous amount of money he was making. And yet, he blew it up. I love him, I wish him the best, he should live in good health for the rest of his life, but I don’t know if I want to get in business with him for any length of time.”

And while Sheen understands Cryer may still have concerns, he insists he’s changed since becoming sober nearly eight years ago.

“I think he’s justified to feel that way, because that’s kind of the historical pattern, but that’s not the case today,” Sheen told People. “And I’m going to go out of my way to make him wrong every single day.”

aka Charlie Sheen premieres on Netflix Sept. 10. Until then, keep reading for more celebrity feuds.

Tan France vs. Bobby Berk

Bobby (pictured second from left) addressed rumors of a falling out with Tan (middle) in January 2024, two months after he announced his exit from Queer Eye after eight seasons.

“I want people to know that Tan and I—we will be fine,” he told Vanity Fair. “There was a situation, and that’s between Tan and I, and it has nothing to do with the show. It was something personal that had been brewing—and nothing romantic, just to clarify that.”

In March 2024, Tan responded to allegations that he had campaigned to replace Bobby on Queer Eye with his friend Jeremiah Brent.

“Netflix and the production companies did a full-on casting. I didn’t put my friend up for the job. They ended up getting it because they were the best person for the job,” he said on Instagram. “But I didn’t get them hired by getting rid of somebody else.”

Shannen Doherty vs. Alyssa Milano

Following years of rumors of a feud between the two, on a December 2023 episode of her podcast Let’s Be Clear, Shannen’s former Charmed costar Holly Marie Combs alleged that Alyssa had once made an ultimatum to a show producer to choose between herself and Shannen, which ultimately led to the latter leaving the show in 2001.

In February 2024, Alyssa said on Instagram, “I did not have the power to get anyone fired” and that “this was so long ago that any retelling of these stories from anyone is just revisionist history.”

A day later, Shannen said at a panel event at MegaCon Orlando, “There is no revisionist history happening in the truth that I know we told.”

Shannen passed away in July 2024 after a yearslong battle with cancer.

Sharon Osbourne vs. Ashton Kutcher

In September 2023, while playing a game called Stir the Pot with her daughter Kelly Osbourne on E! News, Sharon said the That ’70s Show alum was the rudest celebrity she had ever met, branding him, a “rude, rude, rude, rude little boy” and a “dastardly little thing.”

He did not respond to her remarks publicly.

Five years prior, Sharon told Larry King that when Ashton appeared on The Talk in 2014, he had an “attitude” after she got his name wrong.

“He goes, ‘What are you, what have you done in this industry?'” she recalled. “And I was like, ‘Kid, don’t start with me, because I’m gonna eat you up and s–t you out.’ So I was just like, ‘You don’t know what you’re dealing with, kid.'”

Maren Morris & Cassadee Pope vs. Brittany Aldean

In August 2022, Cassadee and Maren traded harsh words with Brittany, wife of fellow country star Jason Aldean, after she shared an Instagram Reel of herself applying makeup on Aug. 23, writing, “I’d really like to thank my parents for not changing my gender when I went through my tomboy phase. I love this girly life.”

JoJo Siwa vs. Candace Cameron Bure

During a 2022 TikTok challenge, JoJo Siwa described Candace Cameron Bure as the “rudest” celebrity, later explaining that she felt snubbed when Bure once refused to take a picture with her on a red carpet. Shortly after the dig, however, the Full House alum apologized: “I kind of broke your 11-year-old heart. I didn’t take a picture with you. Ugh! I feel crummy, I feel—JoJo, I’m so sorry.”

The two made amends. But months later, Candace was asked if she expects the Great American Family network, of which she serves as chief creative officer, to feature same-sex couples as leads in holiday movies. She said no, adding, “I think that Great American Family will keep traditional marriage at the core.”

JoJo, who came out as a member of the LGBTQ+ community in 2021, wrote on Instagram that the actress’ comment is “rude and hurtful to a whole community of people.”

Courtney Love vs. Olivia Rodrigo

Back in June 2021, Courtney Love accused Olivia Rodrigo of copying her band Hole‘s album cover for a promotional photo without giving credit. Olivia responded, “Love u and live through this sooooo much.” Courtney then replied, “Olivia – you’re welcome. My favorite florist is in Notting Hill, London! Dm me for deets! I look forward to reading your note [winking face emoji].”

Henry Winkler vs. Tom Hanks

During an appearance Watch What Happens Live, the Happy Days actor was asked why he didn’t get along with the Forrest Gump star on the set of the 1989 flick Turner & Hooch.

“I was directing that movie for 13 days and then I was called into [producer] JeffKatzenberg‘s office and he said, ‘You have everything with you? Go home,'” he said.

Winkler did, however, seem to get along with Hanks’ four-legged co-star. “I got along great, great with that dog,” he said. “Love that dog.”

He also refused to admit if he’s even seen the flick. 

Heidi Montag vs. Lauren Conrad

“You know what you did!”

Fans of The Hills will remember that iconic line, delivered by Lauren on the season three premiere. Their feud began when Heidi started dating her now-husband SpencerPratt,andhit its peak when Lauren accused Heidi and Spencer of starting a rumor that she had made a sex tape with Jason Wahler.

Dwayne Johnson vs. Tyrese Gibson

The costars reignited their ongoing feud when Tyrese publicly called out Dwayne on Instagram after the Fast and Furious 9 release date was pushed back to April 2020. That same day, it was announced that a Fast and Furious spinoff starring Dwayne and Jason Statham would hit theaters in 2019. The following month, Tyrese threatened to quit Fast 9 if Dwayne was in the movie.

Tyrese then opened up about the feud, telling Van Lathan on The Red Pill podcast, “I have yet to talk to The Rock to this day, and we will have a conversation.” He shared that he did have a conversation with the former wrestler’s producing partner, but not the actor himself.

“I found myself being the messenger on behalf of various people associated to the franchise, but stupid me was the only one who went public about those feelings, which is my own fault,” Tyrese said. “It’s not professional, it’s not cool.”

Taylor Swift vs. Katy Perry

No more bad blood here.

Taylor and Katy had been in a feud for years, even allegedly inspiring Taylor’s song “Bad Blood.” The drama, which reportedly started over a backup dancer and competing tours, came to an end after Perry sent Taylor a literal olive branch before her Reputation Tour kickoff.

“So I just got to my dressing room and found this actual olive branch,” Taylor said in an Instagram video. “This mean so much.”

Taylor captioned the video, “Thank you Katy.”

Kim Cattrall vs. Sarah Jessica Parker

Sex and the City costars Kim and SJP had dodged feud rumors for years. But they were reignited after Kim decided not to return for a third movie and made comments about her costar that raised eyebrows.

“What was your reaction to Kim Cattrall telling Piers Morgan that you were never friends just colleagues?” Andy Cohen asked SJP on a Sept. 2017 episode of Watch What Happens Live.

As she explained, “Just…heartbroken. I mean that whole week, you and I spoke about it because I was just…I don’t know I found it really upsetting because that’s, you know, that’s not the way I recall our experience.”

“So…it’s sad but I’m kind of…I don’t know, I always think that what ties us together is this singular experience is the thing. It was a professional experience but it became personal because it was years and years of our lives. So I’m hoping that that sort of eclipses anything that’s been recently spoken,” she continued. “That many years spent doing something so special that people had a connection with is such a privileged.”

And though they didn’t film scenes together, Kim did make a small appearance on And Just Like That.

 

Madonna vs. Elton John

The iconic singers have been feuding since 2004. While accepting the Classic Songwriter Award at the Q Awards that year, Elton said to attendees, “Madonna, best f–king live act? F–k off! Since when has lip-syncing been live? Sorry about that, but I think everyone who lip-syncs in public on stage, when you pay like 75 quid to see them, should be shot.”

Shonda Rhimes vs. Katherine Heigl

The former Grey’s Anatomy star sparked a feud with the series creator in 2008 when she removed her name from the Emmy Awards consideration. The actress stated that her reason for the move was because she wasn’t “given the material to warrant a nomination.”

Shonda later opened up about Katherine’s decision during an interview with Oprah Winfrey on Oprah’s Next Chapter in 2012. “On some level it stung and on some level I was not surprised,” she said. “When people show you who they are, believe them. I carry that [mantra] with me a lot. It has served me well.”

Nicki Minaj vs. Cardi B

It was the New York Fashion Week fight heard ’round the world when Nicki and Cardi got into a heated altercation at the Harper’s Bazaar Icon party. The following month, Cardi opened up about the catalyst for the fight with Nicki.

“For a while now she’s been taking a lot of shots at me,” Cardi said in W magazine’s Art Issue. “I spoke to her twice before, and we came to an understanding. But she kept it going.”

The real spark of the fight came when Cardi saw that Nicki had allegedly liked and then unliked a tweet about Cardi’s parenting skills, which Nicki has denied.

“I was going to make millions off my Bruno Mars tour, and I sacrificed that to stay with my daughter,” Cardi continued. “I love my daughter. I’m a good-ass f–king mom. So for somebody that don’t have a child to like that comment? So many people want to say that party wasn’t the time or the place, but I’m not going to catch another artist in the grocery store or down the block.”

Kanye West vs. Taylor Swift

Tension betweenKanye and Taylor first started in 2009, when the “Stronger” rapper took the stage during her acceptance speech at the MTV Video Music Awards. Years later, the two would make up and even become friends, but that came to an end in 2026 after the release of his song “Famous,” in which he name-checks the “End Game” singer.

In February 2025, one day before the Grammys, Kanye updated his Instagram to follow only Taylor. He added no further comment, and the fellow musician did not respond publicly to the move.

Mariah Carey vs. Jennifer Lopez

“I don’t know her.”

It’s been over 15 years sinceMariah and J.Lo’s “feud” has been going on. It all started when the Queen of Christmas was asked to give her opinion on several singers during an interview. When asked her opinion on Jennifer, she replied, “I don’t know her.”

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