If you haven't checked in on the Sheen household lately, things look a whole lot different than they did during the "winning" era. Honestly, it’s wild how fast time moves in Hollywood. One minute you’re reading about custody battles and the next, Charlie Sheen is basically a "soccer dad" to a pair of teenage boys while his older daughters navigate the messy world of TikTok and reality TV.
People are constantly Googling charlie sheen kids ages because, frankly, the math is getting confusing. He has five kids spanning three different decades. We’re talking about a range from "just starting high school" to "solidly middle-aged."
Let’s break down exactly who these kids are, how old they are right now in 2026, and why the family dynamic is more complicated than a scripted sitcom.
The Big Sister: Cassandra Jade Estevez (41)
Most people forget about Cassandra. She’s the eldest, born way back in 1984. If you’re doing the math, Charlie was just 19 when he had her with his high school sweetheart, Paula Profit.
Cassandra is 41 years old now.
Unlike her younger siblings, she has mostly stayed out of the spotlight. She’s been married to her husband, Casey Huffman, since 2010. She also made Charlie a grandfather over a decade ago when she had her daughter, Luna. It’s kinda surreal to think of Charlie Sheen as a grandpa to a pre-teen, but here we are. Cassandra has always been the "rock" of the family, reportedly staying close to her dad even during his most turbulent years.
💡 You might also like: Why the Jordan Is My Lawyer Bikini Still Breaks the Internet
The Richards Era: Sami and Lola
This is where the public drama usually lives. Charlie’s marriage to Denise Richards was legendary for its highs and very public lows. They have two daughters who are now full-blown adults making their own headlines.
Sami Sheen (21)
Sami was born on March 9, 2004, making her 21 years old.
She’s probably the most "famous" of the bunch right now. She’s been very vocal about her life on social media and even joined OnlyFans a few years back, which—as you can imagine—caused quite a stir with her dad at first. Lately, things have been a bit rocky. As of early 2026, Sami has been featured on the Bravo show Denise Richards & Her Wild Things, where she admitted she hasn't really spoken to Charlie in months. She’s also been caught up in some public TikTok drama involving her younger sister.
Lola Rose Sheen (20)
Lola followed shortly after on June 1, 2005. She is currently 20 years old.
While she used to be the more private sister, she’s recently been dragged into the spotlight due to a public feud with Sami. There were some wild accusations floating around about Lola supposedly dating Sami's ex-boyfriend—something Lola flatly denied on TikTok before deleting the posts. Despite the sisterly spat, Lola is reportedly much closer to Charlie than Sami is right now, even calling their relationship a "blessing."
The Twins: Bob and Max Sheen (16)
The youngest of the pack are the twin boys Charlie shares with Brooke Mueller. Bob and Max were born on March 14, 2009.
They are currently 16 years old.
📖 Related: Pat Lalama Journalist Age: Why Experience Still Rules the Newsroom
For a long time, these boys were at the center of a massive custody tug-of-war. Because of Brooke’s struggles with sobriety and Charlie’s own past issues, they spent time being cared for by Denise Richards and their grandparents.
However, the 2026 update is actually pretty grounded:
- Single Dad Life: Charlie has been the primary caregiver for the boys for several years now.
- Normalcy: He’s described them as "really cool, really smart, and really funny."
- Interests: Bob has apparently shown an interest in filmmaking, while both boys mostly stay off social media, which is probably a smart move considering their family history.
- Sobriety Impact: Charlie’s eight-plus years of sobriety have seemingly allowed him to be the present father these boys needed during their mid-teens.
Why the Age Gaps Matter
The massive spread in charlie sheen kids ages—from 16 to 41—means Charlie has lived through several different "versions" of fatherhood.
He was a kid himself when Cassandra was born. He was at the height of his Two and a Half Men fame when Sami and Lola were toddlers. And he was arguably at his lowest point when the twins were babies.
Raising 16-year-old boys as a 60-year-old sober man is a world away from the chaos of 2011. He’s often joked that having teenagers at his age feels like having "roommates" who don't pay rent. It’s a relatable sentiment, even if your dad isn’t a world-famous actor.
👉 See also: Why Sexy Pictures of Mariah Carey Are Actually a Masterclass in Branding
Reality Check: The 2026 Family Dynamic
Don’t let the "sober dad" headlines fool you into thinking it's all sunshine and roses. The Sheen-Richards-Mueller blended family is still messy.
The recent falling out between Sami and Lola shows that the trauma of growing up in the paparazzi lens doesn't just vanish. Sami has been open about the fact that her childhood was "pretty bad" for the first 13 years. That’s a lot of baggage to unpack in your early 20s.
Meanwhile, Brooke Mueller has been more present lately, celebrating birthdays with the twins, but the court documents still lean heavily in Charlie's favor regarding custody, provided he maintains his sobriety.
What to Watch Next
If you're following the Sheen family saga, here is how you can stay updated on the latest developments without getting lost in the tabloid noise:
- Check TikTok for Sami and Lola: Most of their "real" updates happen in short-form video. It’s where they vent and where the actual news usually breaks first.
- Monitor Bravo: With Denise Richards back in the reality TV game, more details about the girls' relationship with Charlie are likely to surface in upcoming episodes.
- Look for the Documentary: Charlie has teased a documentary that covers his life and recovery; this will likely be the first time we see the twins, Bob and Max, speak for themselves as young adults.
The most important takeaway? Charlie Sheen's kids aren't kids anymore. They are a group of Gen Z and Millennial adults trying to figure out their own identities outside of their father's "tiger blood" legacy.