Charlie Sheen comes from a famous family — and he’s passing on the torch to daughters Cassandra Estevez, Sami Sheen and Lola Sheen, and twin sons Bob and Max Sheen.
The Two and a Half Men alum became a father for the first time in 1984 when he welcomed Cassandra with his high school sweetheart, Paula Speert. Their relationship came full circle in 2010 when Charlie walked his eldest daughter down the aisle to wed her own childhood sweetheart, Casey Huffman. Three years later, the Scary Movie 3 star became a grandfather when Cassandra and her husband welcomed their daughter, Luna.
“It’s impossibly a most wondrous day,” Charlie gushed to TMZ about the birth of his first grandchild. “My bucket list is a thimble!”
During his marriage to Denise Richards — the Wall Street star and Real Housewives of Beverly Hills alum were married from 2002 to 2006 — Charlie went on to welcome two more daughters: Sami, born in 2004, and Lola, born in 2005. Despite his many ups and downs with the Wild Things actress — as well as his highly publicized behavior in the public eye — Richards ensures that their daughters are protected from hearing about the actor’s more controversial moments.
“There’s a lot that the kids don’t know about their dad and I want to keep it that way,” Richards said on a 2020 episode of RHOBH. “Even though he’s Charlie Sheen, that is still to them their dad. I never talk badly about him and I want him to be part of their lives because I met a lot of the women that Charlie entertained and a lot of them had father-daughter issues. And I do not want that to be our girls.”
One year later, Sami made headlines when she left high school and went to live with her dad amid drama with Richards.
“Sam’s amazing. I love her and all my children unconditionally,” Charlie exclusively told Us at the time via his rep, Jeff Ballard. “We’re having a ball. GED here we come!”
Though the father-daughter duo later butted heads over Sami’s decision to join OnlyFans — while having her mom’s full support — Charlie ultimately agreed with Richards and championed Sami’s new pursuit.
“Now more than ever, it’s essential that Sami have a united parental front to rely upon, as she embarks on this new adventure,” the Anger Management alum exclusively told Us through Ballard. “From this moment forward, she’ll have it abundantly.”
In addition to his three daughters, Charlie is also the father of twins Bob and Max, born in 2009, with ex-wife Brooke Mueller. “They’ve made me a better man,” the Rookie actor told In Touch two months after their birth.
While he and Mueller have had their own share of drama and custody issues, in 2022, they ultimately came to a custody agreement over their sons.
“Mr. Sheen and Ms. Mueller recognize together the great benefit to their children in peacefully, privately coming to terms focused on the family’s overall best interests,” Charlie’s attorney, Gregory J. Pedrick, Esq., told Us in a statement at the time. “They should be applauded for making that happen.”
Keep scrolling to get to know Charlie’s five children:
