Charlie Sheen and Denise Richards’ Ups and Downs Through the Years

More than a decade after saying “I don’t,” ex-spouses Charlie Sheen and Denise Richards are still in each other’s orbits. “It’s surreal when you start to see your kids become adults. It makes me cry,” Richards confessed in an April 2018 episode of RHOBH, referring to her and Sheen’s daughters: Sam and Lola. (Richards also has an adopted daughter Eloise.) “I just feel like I f--ked up a lot with their dad. I don’t want them to look back at their childhood and remember [arguments].” She added: “My girls have been through a lot. How I chose to relate to the dysfunction that was going on with their father was to hide it from the kids. I don’t know if I did a disservice or not. … It just made me realize how fast it goes. Life is so short and their childhood is so short.” [sendtonews type="float" key="aHxBDV3Twn-2835828-14453"] Following his relationship with Richards, Sheen married Brooke Mueller in 2008. The former couple welcomed twins Bob and Max in 2009, split in 2010, and finalized their divorce in 2011. In 2014, he got engaged to former adult film star Brett Rossi but split from her later that year. In February 2019, the Anger Management alum exclusively told Us Weekly he was single and was resolved to not walk down the aisle again. “Marriage again? Yeah, that’s ‘no,’ all caps,” he said at the time. “When you’re really bad at something, there’s no reason to keep pursuing it.” Relive Sheen and Richards’ relationship before, during and after their marriage in the gallery below.

Sheen gave his then-fiancée of less than a month a smooch after winning a Golden Globe Award for Best Performance by an Actor in a Television Series-Musical/Comedy for his role in Spin City on January 20, 2002. "I still care for him very much and want him well," Richards told Matt Lauer in the summer of 2011. "He's a survivor and if anyone can pull themselves together, it’s Charlie."

Sheen and Richards appeared at the Undercover Brother premiere at Universal Citywalk in Universal City, California, looking happy and smiling on May 30, 2002. The couple married shortly after on June 15, 2002. Richards admitted to Lauer in 2011 that she was trying to shield her daughters from Sheen's public troubles. "I was just lying to them about so much and covering up things and totally lying," Richards said. "It was just getting too confusing that I had to sit down with them."

Richards and Sheen appeared at the Scary Movie 3 premiere in Westwood, Calif. on October 20, 2003. Richards, who was pregnant with their daughter Sam, looked stunning in a sexy, black floral dress while Sheen wore a black and blue suit. "I want to have a great relationship [with Sheen]," Richards told Jeanne Wolf on June 26, 2012. "He's the father of our daughters and we maintain a good friendship. I like being around him and I think it's important for our kids."

The pregnant couple arrived at the L.A. premiere of The Big Bounce at the Mann's Village on January 29, 2004 in Westwood, Calif. "I have a sense of humor about everything," Richards told Wolf about Sheen's past antics. "I don't like toxic energy and I don't harbor grudges. You move past stuff. I don't think it's healthy to hang on to stuff."

Richards had a recurring role on Two and a Half Men as Sheen's ex who comes back into his life with a little more baggage than when she left. "Denise was very clear with Charlie that he had to be on his best, best behavior if they were to [maintain a healthy relationship]," a source told Us. "She didn't want to put the girls through another nightmare."

A pregnant Richards and Sheen attended the 11th Annual Screen Actors Guild Awards on Febraury 5, 2005. The actress filed for divorce from Sheen in March 2005. They briefly reconciled, but Richards filed again in April 2006. "Oh, he likes 20-year-olds," Richards told Wolf in 2012 of the prospect of the actors getting back together. "I'm past his age range!"

Sheen and Richards grabbed dinner at Da Tommaso in New York City on October 13, 2011. "He's doing well," Richards told Wolf about Sheen in 2012. "He's focused on his show [Anger Management on FX] and the kids and he is who he is, he makes no bones about it, and I also think that's why a lot of people like him and are attracted to him."

Richards tweeted this photo of Sheen, her daughters and herself striking a family pose. "She still looks f--cking great," Sheen said in a June 2012 issue of Rolling Stone. "Do I want to [have sex with her]? Yeah! Does she? Don't know."

Sheen, Richards and daughters Sam and Lola took in a Mets-Yankees game at the Mets' Citi Field around the time the actress guest-starred on Anger Management. "It was more awkward for everyone on set watching," Richards later said of filming her scenes. "We looked around and were like, 'Everyone is staring at us.'"

In a Father’s Day 2015 Twitter rant, Sheen called Richards the “worst mom alive” and an “evil terrorist sack of landfill rash” who “couldn't act hot in a fire or wet in a pool.” Afterward, the actress retweeted a Leeza Gibbons quote reading, “The less you respond to negative people, the more peaceful your life will become.”

“Charlie, when I married him, he wasn’t a bad boy,” Richards said on a November 2015 episode of the podcast “Allegedly With Theo Von and Matthew Cole Weiss,” explaining that her former groom wasn’t struggling with drugs when they walked down the aisle. “He was sober for almost four years. He was a very different person. His lifestyle was very, very different. He was a former bad boy, I guess.”

Richards sued her ex-husband in January 2016, claiming he had abandoned a trust he had created for his kids and that he had sent them obscene texts about her. For his part, Sheen told TMZ that the lawsuit was “a desperate attempt to get more money.”

Bygones? Sheen didn’t attend Richards’ September 2018 wedding to Phypers but sent his congratulations to the happy couple. “[He] wishes them nothing but happiness!” Sheen’s rep told Entertainment Tonight at the time.

In a March 2019 episode of The Real Housewives of Beverly Hills, Richards said she invited Sheen to her wedding. “Even if he did bring a prostitute as his date, I wouldn’t care. It’s just, it is what it is,” she said. “No matter what’s gone down with Charlie and I, I invite Charlie to anything having to do with the kids and I.”

During the Real Housewives of Beverly Hills season 9 reunion, the reality star mentioned that Sheen was “supportive” of her involvement with the Bravo show and that she had moved closer to him to offer assistance following his HIV diagnosis. “A lot of people judged me for that, but I wanted him to be the best dad he could be, for him, for our girls,” she said.

In an episode of the “Daddy Issues” podcast, Richards revealed she “had to do” her 2008 E! reality show, Denise Richards: It’s Complicated, to earn money during her divorce from the Machete Kills star. “[Sheen] said he wanted to bleed me dry, and he did,” she added. “Those legal fees add up quite fast.”

The exes’ relations took a turn for the worse in September 2019 when Richards filed court documents claiming that Sheen owed her $450,000 in back child support and that he had “squandered over $24,000,000 from the sale in his interest in Two and a Half Men to pay his personal debts and to support his extravagant lifestyle at the expense of support payments for his children.” The Hot Shots actor responded to the legal action in a statement to The Blast  saying, “D and her legal posse traffic only in fiction. … My day in court is painfully overdue. She is behaving like a coward and the truth will prevail.”

Richards and Sheen were at a good place in their coparenting relationship, despite the former couple’s custody drama unfolding on season 10 of The Real Housewives of Beverly Hills a month prior. “Communication's great with him,” Richards told Us exclusively on May 4. “He doesn't watch the shows, so I don't even think he knows [what’s airing], but he knows obviously when you file something in court that it's public, and he and I have dealt with this stuff for, gosh, 14, 15 years. We try to keep it separate from things, but he hasn't even said anything other than very positive. It's all good.”

After Sami made headlines for alleging via TikTok that she was “trapped in an abusive household” and “would go days without eating or sleeping” because she was “insanely depressed” in 2020, Sheen confirmed that his and Richards’ eldest daughter moved in with him and dropped out of high school.

“Sam’s amazing. I love her and all my children unconditionally,” Sheen's rep, Jeff Ballard, told Us. “We’re having a ball. GED here we come!”

According to a source, Richards, who had not yet publicly acknowledged her daughter’s video, was “saddened” by the station.

”Denise set normal rules that any parent would be setting. She’s a mom and a parent and there are rules. She didn’t want to follow the rules,” the source said. “Charlie didn’t support implementing Denise’s rules. He has a different way of parenting and Sami decided to live with her dad. Denise loves her daughter very much.”

The former couple continued to disagree on child support payments after a judge ruled that Sheen no longer had to pay Richards after Sami moved in with him. While the actor celebrated his “extremely fair” win while leaving court in October 2021, a source told Us that Richards felt her ex wanted her to miss the hearing. “She wasn’t there because she is working out of state which Charlie was well aware of and Denise was never served this court date. He did this on purpose,” the source said at the time.

While the source claimed that Richards hasn’t received money from Sheen for child support in “at least four years,” his attorney told the judge that the actor was overpaying in recent years.

During an appearance on the “Jeff Lewis Has Issues” podcast, the Wild Things star explained that she and her ex have “always been on different pages from the beginning” when it comes to parenting.

“I just don't agree with certain things. But that's OK," she said about her relationship with Sheen. "You can agree to disagree. There are certain rules and I enforce them. And [at Sheen’s], there’s different rules at that house and that’s okay.”

After Sami joined the NSFW site OnlyFans, Sheen hinted that he believed Richards was to blame for his eldest daughter's decision. “She is 18 years old now and living with her mother,” he told Us at the time. “This did not occur under my roof. I do not condone this but since I’m unable to prevent it, I urged her to keep it classy, creative and not sacrifice her integrity.”

He later changed his tune after the Drop Dead Gorgeous actress defended Sami and OnlyFans in a lengthy Instagram post, saying that Richards made "salient points" about the app. “Now more than ever, it’s essential that Sami have a united parental front to rely upon, as she embarks on this new adventure,” Sheen told Us. “From this moment forward, she’ll have it abundantly.” 

When Richards made her own debut on the platform a few days later, her ex offered his support in another statement, saying, “Go get ’em, Denise.” An insider also told Us that the duo had worked things out after their brief spat. “She and Charlie have made peace now and understand each other,” the source explained. “He’s saying more power to them both and isn’t going to cause any fuss.”

“I’m always in a good place with him,” Richards exclusively told Us of her coparenting relationship with Sheen following their conflicting views over daughter Sami’s OnlyFans venture. “I think it’s great to be able to support one another and to not have judgment of what something may or may not be.”

Nearly two decades after their messy split, Richards supported her ex-husband at the premiere of his Netflix doc, aka Charlie Sheen. The exes posed together on the red carpet.