Charlie Sheen’s 5 Kids: All About Cassandra, Sami, Lola, Bob and Max

Charlie Sheen’s crew includes more than that Two and a half Men.

In fact, the actor — who has been married and divorced three times (to Donna Peele, Denise Richards and Brooke Mueller) — has five children of his own, ranging in age from 14 to 39. Sheen first became a father at the age of 19 when his daughter Cassandra was born with his high school girlfriend Paula Profit in 1984. Two decades later, he had daughters Sami and Lola with Richards in 2004 and 2005, and twin sons Bob and Max with Mueller in 2009.

But fatherhood has been fraught with custody and child support battles for Sheen, and he’s also dealt with his own personal issues over the years — including drug and alcohol addiction, an HIV-positive diagnosis and his infamous 2011 layoff. Two and a half Men. However, Sheen has often cited his children as his inspiration for getting sober.

One such moment occurred in 2011 when Sheen made a comeback after being diagnosed with HIV. The actor later recalled an incident where he was too drunk to take one of his daughters to an appointment – and knew he had to make a change.

“I forgot one morning that my daughter had a meeting that I promised to take her to, and I had already had a few drinks that day,” he told PEOPLE in December 2023, referring to his daughters Sami and Lola. “So I had to call my friend Tony to drive us. We got her on time but it broke my heart because she was in the back seat and I could just tell she was thinking, ‘Why isn’t Dad driving?’ So I came home and sat with it the rest of the day. And the next morning I just stopped.”

Charlie Sheen opens up about being a single dad to his teenage twins (Exclusive)

Sheen has now been sober since 2018, and people around him consider his recovery “remarkable.”

“I have a very consistent lifestyle now. It’s all about being a single dad and raising my 14-year-old twins, Max and Bob,” he told PEOPLE exclusively.

Currently, Sheen is taking steps to protect his teenagers, filing an ex parte petition in January 2024 with new child custody provisions that include his ex-wife Mueller’s sobriety. While the former couple currently share joint legal custody of Max and Bob, Sheen will get full custody of the twins if Mueller returns, according to court documents obtained by PEOPLE.

Here’s everything you need to know about Charlie Sheen’s five children.

Cassandra Estevez, 39

Charlie Sheen with daughter Cassandra at the premiere of “The Mighty Ducks” in 1992.

Sheen had his first child, Cassandra Jade Estevez, with his high school girlfriend Paula Profit on December 12, 1984 – when Sheen was just 19 years old.

In September 2010, Sheen was there to walk his oldest daughter down the aisle when Estevez married her childhood sweetheart Casey Huffman. “He was obviously very proud of her,” the couple’s wedding planner, Jill La Fleur, told PEOPLE. “He had a big smile on his face.”

Three years later, in July 2013, Estevez made Sheen a grandfather when she and Huffman welcomed their own daughter, Luna Huffman.

“Hey Luna, welcome to my planet!” Shine chirped at the time of his granddaughter’s birth.

Sheen has praised Cassandra for years, particularly when he revealed his HIV-positive status to her in November 2015. “She’s tough like her dad,” Sheen said in an interview with Matt Lauer on Today. “She was a rock star in that regard.”

Sami Sheen, 20

Sami Sheen. Sami Sheen on Instagram

Sheen’s second daughter — and first with Richards — Sami Sheen was born in Los Angeles on March 9, 2004. Over the years, the 20-year-old has appeared on several television shows with her parents, including a 2004 episode of Two and a half Menreality series from 2008 Denise Richards: It’s complicated and The Real Housewives of Beverly Hills.

In September 2021, Sami posted a series of TikToks revealing that she had dropped out of high school and moved in with her father — a move that led to a “strained relationship” between the teenager and her mother, Richards.

However, by June 2023, Sami had moved into her own apartment, and a source told PEOPLE, “Denise helped her get everything set up and decorated and settled in. Now they’re really closer than ever. Denise really wants to keep the girls close to her.” He doesn’t want to push them away.”

All about Denise Richards and Charlie Sheen’s daughter Sami Sheen

Sami Sheen and Charlie Sheen. Sami Sheen on Instagram

A few months after Sami turned 18, she started posting content on OnlyFans, a subscription platform for mostly adult content. In a Q&A on her Instagram Stories announcing her new venture, Sami told followers she’s focusing on body positivity on the platform.

“The only thing that’s important is to make sure you agree with what you’re posting and remember that all bodies are beautiful,” she explained.

While Sami’s mother Richards has been supportive of her OnlyFans career – saying she admires her daughter’s “confidence” – her father feels differently. In June 2022, Sheen told E! News that he “has not forgiven” his daughter’s decision to join the platform. “But since I can’t prevent it, I urged her to be elegant, creative and not sacrifice her integrity,” he added.

Lola Sheen, 18

Selfie of Lola Sheen. Lola Sheen on Instagram

Sheen had his third and second child with Richards, Lola Rose Sheen, on June 1, 2005. She was born just three months after Richards filed for divorce from Sheen in March 2005.

Now 18-year-old Lola leads a rather private life, especially when it comes to social networks. Although she rarely posts, the teenager shared snaps from her adventures in Lake Tahoe and Hawaii, as well as her glam edit.

Lola Sheen and Charlie Sheen in 2017 Charlie Sheen Instagram Denise Richards and Charlie Sheen Relationship Timeline

Sheen has praised his youngest daughter on social media in the past, calling her “sweet and sparkly” on Instagram in April 2017. Richards has also marked Lola’s milestones on Instagram – recently wishing her a happy 18th birthday.

“Happy 18th birthday my Lola girl! I can’t believe you’re 18… it went by so fast.. I’m so proud of you and you’re amazing and beautiful and I love your heart so much,” the actress wrote. “You’re starting a new chapter and the best is yet to come. I love you so much and I’m so happy you’re celebrating in your favorite place.”

Bob and Max Sheen, 15

Bob and Max Sheen. Charlie Sheen Instagram

Sheen became a father to a boy when his third wife, Brooke Mueller, gave birth to twin sons, Bob and Max Sheen, on March 14, 2009. The boys were born six weeks premature and Max remained in hospital due to difficulty gaining weight and joined his twin brother at home in April 2009.

Less than two years later, Mueller and Sheen filed for divorce, and the twins were later removed from Mueller’s custody when they were 4 years old due to her allegedly strange behavior. During this time, the boys were temporarily placed in Richards’ custody because Sheen was unable to care for them.

Today, however, Max and Bob live full-time with their father, who raised them as a single father. “I’ve mostly raised my 14-year-olds,” he told PEOPLE in December 2023. “Their mom has been trying to figure out some things on her end, so she’s not in the story too much right now.”

“They’re really cool, really smart and really fun,” the actor added of his boys.

Although Sheen rarely shares photos of Bob and Max, the trio attended a Miami Marlins vs. Los Angeles Angels baseball game — where they were able to meet Marlins second baseman Jazz Chisholm Jr. after the game — in April 2022.

“What a day!” Sheen tweeted following the game. “Thank you so much @j_chisholm3 for the incredible thrill of watching you play today and the honor of meeting you afterward! My sons Bob and Max will never forget their “first” game.”

In January 2024, Sheen was granted an emergency order to get sole custody of his sons if Mueller fails a drug test. The former couple currently have joint legal custody of Max and Bob and previously agreed that Sheen would get sole custody if Mueller returns for a review in 2022.

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Source: HIS Education