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

Charlie Sheen welcomed his first child, Cassandra, when he was 19 years old

Charlie Sheen's crew includes more than just 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 welcomed 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 both custody and child support battles for Sheen, and he's also dealt with his own personal troubles over the years — including drug and alcohol addiction, an HIV-positive diagnosis and his infamous firing in 2011 from Two and a Half Men. However, Sheen has often cited his children as being his inspiration for getting sober.

One such moment came in 2011 when Sheen relapsed following his HIV diagnosis. The actor later recalled an incident where he was too intoxicated to take one of his daughters to an appointment — and knew he needed to make a change.

"One morning I'd forgotten my daughter had an appointment I'd promised to drive her to, and I'd already had a couple of pops that day," he told PEOPLE in December 2023, referring to his daughters Sami and Lola. "So had to call my friend Tony to take us. We got her there on time, but it broke my heart because she was in the backseat and I could just tell she was thinking, 'Why isn't dad driving?' So I got home and sat with that for the rest of the day. And the next morning I just stopped."

Related: Charlie Sheen Opens Up About Being a Single Dad to His Teenage Twin Boys (Exclusive)

Sheen has now been sober since 2018, and those around him view his recovery as "extraordinary."

"I have a very consistent lifestyle now. It's all about single dad stuff, and raising my 14-year-old twin boys Max and Bob," he told PEOPLE exclusively.

Currently, Sheen is taking steps to protect his teenage boys, filing an ex parte motion in January 2024 with new stipulations around child custody involving his ex-wife Mueller's sobriety. While the former couple currently share joint legal custody of Max and Bob, Sheen will obtain full custody of the twins in the event of Mueller's relapse, per court documents obtained by PEOPLE.

Here's everything to know about Charlie Sheen's five kids.

Cassandra Estevez, 39

Sheen welcomed his first child, Cassandra Jade Estevez, with his high school girlfriend Paula Profit on Dec. 12, 1984 — when Sheen was just 19.

In September 2010, Sheen was there to walk his eldest daughter down the aisle when Estevez married her childhood sweetheart Casey Huffman. “He was clearly 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 a daughter of their own, Luna Huffman.

"Hey Luna, welcome to my planet!" Sheen tweeted at the time of his granddaughter's birth.

Sheen has spoken highly of Cassandra over the 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 about it."

Sami Sheen, 20

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 Men, the 2008 reality series Denise Richards: It's Complicated and the Real Housewives of Beverly Hills.

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

By June 2023, however, Sami had moved into her own place, with a source telling PEOPLE, "Denise helped her get set up and decorate everything and get settled in. They're really closer than ever now. Denise really wants to keep her girls close to her. She doesn't want to push them away."

Related: All About Denise Richards and Charlie Sheen's Daughter Sami Sheen

A few months after Sami turned 18, she began posting content on OnlyFans, a predominantly adult content subscription platform. In a Q&A on her Instagram Stories announcing her new venture, Sami told followers that she focuses on body positivity on the platform.

"Only thing that matters is making sure you're comfortable with what your posting & remembering 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 did "not condone" his daughter's decision to join the platform. "But since I'm unable to prevent it, I urged her to keep it classy, creative and not sacrifice her integrity," he added.

Lola Sheen, 18

Sheen welcomed his third child and second 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.

The now-18-year-old Lola leads a rather private life, particularly when it comes to social media. Though she rarely posts, the teen has shared snaps from adventures in Lake Tahoe and Hawaii as well as getting her glam done.

Related: Denise Richards and Charlie Sheen's Relationship Timeline

Sheen has praised his youngest daughter on social media in the past, calling her "adorable and ebullient" on Instagram in April 2017. Richards has also commemorated Lola's milestones on Instagram — most 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 & you are amazing & beautiful & I love your heart so much," wrote the actress. "You’re beginning a new chapter & the best is yet to come. I love you so much & so happy you’re celebrating at your favorite place ever."

Bob and Max Sheen, 15

Sheen became a father of boys when twin sons Bob and Max Sheen were born to his third wife, Brooke Mueller, on March 14, 2009. The boys were born six weeks premature, and Max remained hospitalized due to difficulty gaining weight and joined his fraternal 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 erratic behavior. During this time, the boys were temporarily placed in Richards' custody as Sheen was unable to care for them.

Today, however, Max and Bob live full-time with their father, who has been raising them as a single dad. "I've mostly been raising my 14-year-old boys," he told PEOPLE in December 2023. "Their mom has been trying to figure some stuff out on her end, so she's not in the picture too much right now."

"They're really cool, really smart, and really funny," the actor added of his boys.

While Sheen rarely shares photos of Bob and Max, the threesome did attend a Miami Marlins baseball game against the Los Angeles Angels — where they were able to meet Marlin's second baseman Jazz Chisholm Jr. following the game — in April 2022.

"What a day!" Sheen tweeted following the game. "Thank you so much @j_chisholm3 for the mind blowing thrills 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 failed a drug test. The former couple currently have joint legal custody of Max and Bob and previously agreed that Sheen would receive sole custody should Mueller relapse in a 2022 revision.

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