Let’s talk about Charlie Sheen. As part of Hollywood's most iconic families, Charlie has not only made a name for himself in the entertainment world but also as a dad. Best known for his role in Two and a Half Men, Charlie is a proud father to five children—Cassandra, Sami, Lola, Max, and Bob. Each of these kids has a unique story, shaped by Charlie's high-profile romances. Keep reading to learn more about his incredible family and the lives of his children.

Meet Charlie Sheen’s Firstborn, Cassandra Estevez

Charlie Sheen, the son of legendary actors Martin and Janet Sheen, became a dad for the first time in 1984. He welcomed his eldest daughter, Cassandra, with his high school sweetheart, Paula Profit. At just 19 years old, Charlie was already stepping into fatherhood. But here’s the thing—he’s always kept Cassandra out of the spotlight, protecting her from the chaos that often comes with being part of a famous family.

Cassandra, now grown, has a family of her own. In July 2013, she became a mom to her daughter Luna, with her husband, Casey Huffman. When Luna was born, Charlie couldn’t hide his excitement. He told TMZ at the time, “It’s impossibly a most wondrous day.” And let’s just say, becoming a grandpa was definitely a momentous occasion for the New York native.

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The Dynamic Duo: Sami and Lola, Charlie Sheen’s Daughters with Denise Richards

After a brief marriage to his first wife, Donna Peele, Charlie met actress Denise Richards on the set of Good Advice in 2000. Their whirlwind romance led to marriage in 2002, and soon after, they started a family. In 2004, Sami was born, marking the beginning of their blended family journey.

Fast forward to 2022, and Sami made headlines when she announced her decision to join OnlyFans, a subscription-based platform for adult content. Now, this decision didn’t sit well with Charlie. In a statement to Us Weekly, he expressed that while he didn’t condone her choice, he urged her to “keep it classy, creative and not sacrifice her integrity.” But hey, Sami’s mom, Denise, was all about supporting her daughter’s decision, even joining the platform herself.

Charlie Sheen Kids: Actor's Children, Blended Family — Eric Charbonneau/Shutterstock

Denise stood firm in her belief that Sami’s decision wasn’t about whose house she lived in but about trusting her judgment. She expressed, “Sami is 18, and this decision wasn’t based on whose house she lives in. All I can do as a parent is guide her and trust her judgment, but she makes her own choices.”

Not long after Sami’s birth, Lola came along in 2005, making Sami a big sister. However, Charlie and Denise’s marriage didn’t last, and they parted ways later that year. Their divorce was finalized in 2006, but the bond they share through their daughters remains strong.

Introducing the Twins: Max and Bob with Brooke Mueller

In 2008, Charlie married his third wife, Brooke Mueller. Their union was short-lived, but it brought two beautiful additions to Charlie’s family—twin boys Max and Bob, born in 2009. These little ones haven’t shown any signs of following in their dad’s acting footsteps just yet, but who knows what the future holds for them?

Max and Bob have been spotted out and about with their famous father over the years. Even though Charlie and Brooke’s marriage ended in 2010, with their divorce finalized in 2011, the twins continue to enjoy a close relationship with their dad.