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Charlie Sheen is best known as a successful actor, but he’s also, more importantly, a doting father of five. The busy dad has welcomed three daughters and two sons over the course of one relationship and two marriages, and has often gushed over them during public appearances and in media interviews. “I love all my children unconditionally. We’re having a ball,” he once told Us Weekly when discussing his relationship with them and praising one of his daughters’ accomplishments.

Find out more about Charlie’s children and their backgrounds below.

Cassandra

Cassandra Jade Estevez is Charlie’s oldest child. She was born to him and his high school sweetheart Paula Profit in 1984 when he was just 19. Unlike some of Charlie’s other children, Cassandra has chosen to stay out of the spotlight, but she reportedly once pursued acting. She is also known to have reportedly maintained a close relationship with her grandfather, Martin Sheen, and her uncle Emilio Estevez and seems to be on good terms with her dad.

She reportedly married and welcomed a daughter named Luna in 2013. Luna is Charlie’s first grandchild.

Sami

Sami Sheen is Charlie’s second child and first with his ex-wife Denise Richards, whom he was married to from 2002 until 2006. She was born in 2004 and has appeared on television and on casual and professional outings with her parents. She was featured on The Real Housewives of Beverly Hills when her mom was one of the main cast members in 2009 and 2010. After Charlie and Denise’s split, she eventually went from living with her mom to living with her dad, and once called the experience “lovely.”

“Sami is a teenager, who didn’t like her mother’s rules,” a source exclusively told Hollywood Life about the move in 2021. “Like any mother and household, there are rules in Denise’s. She and Charlie have rules and styles of parenting and [they] didn’t see eye to eye. Sami decided she liked Charlie’s rules better and wanted to go and live with her father. Denise is incredibly saddened by all of this, but knows she is doing her best as a mother.”

In 2022, it was reported that Sami went back to living with Denise, and she made headlines when she revealed she made an OnlyFans account, which is a subscription service fans can pay for to see exclusive content, which could include racy photos, from a user. Charlie expressed his disapproval about the decision, in a statement to Us Weekly. “She is 18 years old now and living with her mother. This did not occur under my roof,” he said. “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.”

Meanwhile, Denise’s rep told Hollywood Life, “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.”

Lola

Lola Sheen is Charlie’s third child and second with Denise. She was born in 2005, when Denise and Charlie started having marital issues and the former even got a restraining order on the latter. The couple got divorced just a year after Lola was born and the teen has split spending time with both her mom and dad ever since. “Lola splits time between both Charlie and Denise’s homes,” an insider exclusively told us, “but Denise has been the primary caretaker for the girls for years. She’s an incredible mother who loves her kids and would do anything in the world for them.”

Lola got her driver’s license in 2022 and sometimes appears in her parents’ Instagram posts along with her other siblings. In 2017, Charlie shared an adorable pic of him and her sitting in a car and smiling. “good thing we’re‬ ‪not in the U.K., ‪or my adorable‬ and ebullient 11 year old daughter,‬ Lola,‬ ‪wound be driving!‬ ‪ ❤️©❤️‬ ‪ #ProudPapa,” he wrote in the caption. 

Max & Bob

Twins Max Sheen and Bob Sheen are Charlie’s youngest children and only sons. They were born in 2009 to the former Two and a Half Men star and his ex-wife Brooke Mueller, whom he was married to from 2008 until 2011. Sadly, the boys’ custody arrangements have changed a fair amount over the past few years after Charlie had legal troubles and Brooke reportedly struggled with drug addiction. At one point, Denise was even given custody of Max and Bob. Brooke reportedly checked into a rehab facility in Aug. 2019 while the boys were in the care of her parents.

After going through a custody battle for the twins, it seems things eventually got better between Charlie and Brooke when it was reported they came to an undisclosed financial agreement in regard to child support. Max and Bob are sometimes seen spending time with their dad. One of the most recent outings happened when Charlie and one of the boys went shopping in Malibu, CA on June 14, 2022. They appeared relaxed as they walked beside each other and showed off their similar features.