Meet Charlie Sheen’s five kids with three different wives

Away from the spotlight, the Two and a Half Men star is a father to five children from his three marriages to Donna Peele, Denise Richards and Brooke Mueller. Charlie cited his children as one of the main reasons he chose to get sober. “I have a very consistent lifestyle now. It’s all about single dad stuff, and raising my 14-year-old twin boys Max and Bob,” he told People. In light of the actor’s new documentary, HELLO! takes a closer look at the lives of Charlie Sheen’s five children.

Charlie welcomed his first child with his high school girlfriend Paula Profit in December 1984 when he was just 19-years-old. The doting father walked his daughter, Cassandra, down the aisle in September 2010 when she married Casey Huffman. The couple welcomed their daughter, Luna in July 2013. “She’s tough like her dad,” Charlie shared about his daughter during an interview on TODAY.

The star welcomed his daughter, Sami, with his ex-wife, Denise, in March 2004. The 21-year-old has graced the screen alongside her parents in a 2004 episode of Two and a Half Men, the 2008 reality series Denise Richards: It’s Complicated and the Real Housewives of Beverly Hills. Following her 18th birthday, Sami began posting content on OnlyFans. “Only thing that matters is making sure you’re comfortable with what you’re posting and remembering that all bodies are beautiful,” she explained of her decision. 

However, Charlie shared that he did “not condone” his daughter’s decision to join the platform. “But since I’m unable to prevent it, I urged her to keep it classy, creative and not sacrifice her integrity,” he told E! News. 

During an episode of Denise Richards & Her Wild Things in April 2025, Sami admitted that she and her father “haven’t really spoken much in the past five months.” “It goes in very big chunks with him,” she said. “I think for the first 13 years of my life, it was pretty bad, and then we were okay for a couple years, and now it’s just like, okay.”

Charlie welcomed his second child with Denise in June 2005 – three months after the actress filed for divorce. Unlike her sister, Lola often refrains from the spotlight. However, she hosts her own podcast called Heavenly Bonded.

The star shares twin boys with his third wife, Brooke. The former couple welcomed Bob and Max in March 2009 – six weeks premature. The twins live full-time with their father and were removed from their mom’s custody when they were four years old. “I’ve mostly been raising my 14-year-old boys,” Charlie told People in December 2023. “Their mom has been trying to figure some stuff out on her end, so she’s not in the picture too much right now.” “They’re really cool, really smart, and really funny,” he added.

Charlie and Brooke share joint legal custody of their twins, but a 2022 agreement states that Charlie would receive sole custody in the event of a relapse on Brooke’s part.