Cassandra Estévez
Charlie welcomed his first child Cassandra with his high school girlfriend Paula Profit in 1984 when he was only 19 years old.
While Cassandra has mostly stayed out of the spotlight, she was escorted down the aisle at her 2010 wedding to Casey Huffman by the Two and a Half Men star.
Sami Sheen
Charlie and now-ex-wife Denise Richards welcomed their eldest daughter together on March 9, 2004 two years after they wed.
Sami first entertained the limelight when she appeared on Denise's 2008 E! reality series Denise Richards: It's Complicated as a child.
Over a decade later, she made a name for herself in 2022 when she became an OnlyFans model shortly after turning 18. And the young star's career move has proved to be quite lucrative ever since.
“It opened so many doors for me,” Sami told People in February 2025, “and I've met really cool people doing it, and it's been really rewarding being my own boss and making my own hours and being able to do the things I've always wanted to do.”
Lola Sheen
Lola, who was just 3 when It's Complicated premiered, grew up to be very different than her boundary-pushing older sister.
Born June 1, 2005, she is a woman of God and a devout Christian.
“I can't explain it other than it literally was supernatural,” the restaurant hostess told People in an interview published Feb. 2025 after getting baptized in the church. “Jesus rescued me and he completely rewired my mind. He became my Savior, but also my best friend.”
The teen also shared how religion saved her from the darkness of depression.
“I felt so lost and hopeless, and was just doing my best to make it to the next day,” she admitted on Instagram. “He gave me a light, when I couldn’t find my own, and rescued me from the darkness. Jesus saved me from battling severe anxiety, and gave me a peace that makes no sense.”
Eloise Richards
Following her divorce from Charlie, newly-single Denise adopted her youngest daughter Eloise as an infant in 2011. In 2016, she was diagnosed with a deletion in chromosome 8 which caused developmental delays in walking and speech.
"Eloise is a bright light," the proud mom told People in March 2025. "She just loves everything, and she just embraces it and is just so happy. And the older girls see it too. Sometimes if they go at each other, [Eloise will] just be like... And I'm like, 'I know.' And then they laugh, and then they can kind of get past whatever stupid thing they're fighting about."
Bob Sheen & Max Sheen
Charlie and third wife Brooke Mueller welcomed twin boys Bob Sheen and Max Sheen on March 14, 2009. The couple divorced less than two years later, with Bob and Max living with Denise during their parents' contentious split.
In 2023, Charlie got candid about raising his youngest children as a single dad.
"Their mom has been trying to figure some stuff out on her end, so she's not in the picture too much right now," he told People at the time. "They're really cool, really smart, and really funny."
While they mostly stay out of the spotlight, the twins made a rare appearance at their mom's 47th birthday celebration in August 2024.
The Estévezes
Let's not forget that Charlie (real name Carlos Estévez) was born into a famous family. His dad is legendary actor Martin Sheen (born Ramon Estévez), whose Hollywood career spans more than six decades.
Charlie's older brother Emilio Estévez also followed in their father's footsteps having starred in classic films like The Breakfast Club, St. Elmo's Fire, Mission Impossible and The Mighty Ducks.
The stars also share brother Ramon Estévez and sister Renée Estévez.