Charlie Sheen's 5 Kids: A Guide to His Famous Family

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, Charlie 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 — whom he was married to from 2002 to 2006  — Charlie went on to welcome two more daughters: Sami, born in 2004, and Lola, born in 2005. 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:

The Ferris Bueller’s Day Off star was 19 years old when his high school sweetheart gave birth to Cassandra. Charlie later walked his eldest daughter down the aisle at her 2010 wedding, and became a grandfather when Cassandra and her husband welcomed a baby girl in 2013.

Sami, born in 2004, is Charlie’s eldest daughter with Richards. In 2022, she dropped out of high school and went to live with her dad amid tension with her mom.

Despite Charlie’s initial disapproval of Sami’s decision to join OnlyFans, he ultimately backed Richards’ approval of their daughter’s endeavor. “Now more than ever, it’s essential that Sami have a united parental front to rely upon, as she embarks on this new adventure,” he exclusively told Us at the time. “From this moment forward, she’ll have it abundantly.”

Lola, Charlie’s second daughter with Richards, was born in June 2005 — three months after the reality star filed for divorce from Charlie. The two briefly reconciled before ultimately calling it quits in 2006.

Charlie and Mueller welcomed their twins in March 2009.

Bob and Max were seen on a rare outing with their famous father in April 2023, per photos obtained by Page Six, looking all grown up and identical to their dad.