Charlie Sheen
Charlie Sheen—the son of Martin Sheen and brother to Emilio Estevez—was one of the original "men" in Two and a Half Men, playing Charlie Harper in the first eight seasons of the CBS sitcom opposite Jon Cryer as his on-screen brother. The eighth season was cut short in 2011 amid Sheen's battle with addiction.
He famously clashed with executive producer Chuck Lorre in the press and social media, resulting in his dismissal from the series (and the coinage of the phrases "winning" and "tiger's blood"). His character was killed off and later played as a ghost by Kathy Bates.
After exiting Two and a Half Men, Sheen booked the TV version of Anger Management, which aired from 2012 to 2014 and produced 100 episodes over two seasons. Since, he popped up on The Goldbergs and on the big screen in Scary Movie 5, Machete Kills and 9/11.
In 2023, the actor—who shared in 2015 he is HIV-positive—made a cameo as himself on Lorre's Max series Bookies. He released his memoir The Book of Sheen as well as aka Charlie Sheen in 2025.
Sheen, who has now been sober for years, shares sons Bob Sheen and Max Sheen with ex-wife Brooke Mueller, daughters Sami Sheen and Lola Sheen with ex-wife Denise Richards and daughter Cassandra Estevez from a previous relationship.
Jon Cryer
Jon Cryer starred in all 12 seasons of Two and a Half Men as divorcee Alan Harper, brother to Charlie, father to Jake and friend to Walden.
After the show, he released a memoir and popped up on shows like Mom, The Ranch, NCIS, Robot Chicken and Lady Dynamite among others. Cryer then went on to play Lex Luthor on the TV series Supergirl from 2019 to 2021 as well as Jim Kearney on Extended Family, which ran from 2023 to 2024.
Cryer shares daughter Daisy with wife Lisa Joyner as well as son Charlie with ex-wife Sarah Trigger.
Though Cryer agreed to sit down for aka Charlie Sheen, the two aren’t exactly friends. "We don’t have a relationship anymore," Cryer said on a January episode of Club Random With Bill Maher. "I wish him the best. We have some mutual friends still, and I’ve heard he’s been sober for a while, which is great to hear."
Angus T. Jones
Angus T. Jones played the "half man" in Two and a Half Men, Jake, Alan Harper's son. He became the highest paid child actor on TV at age 17, but then left the series in 2013 after forging down a religious path. However, he did return for the series finale in 2015.
Jones attended University of Colorado Boulder after leaving the sitcom and, at one point, teamed up with Sean Combs' son Justin Combs for a media and events company.
In 2023, he made a cameo as himself on creator Chuck Lorre's Max series Bookies.
Jones continues to lead a life out of the spotlight, but noted in a 2020 Instagram post, "I do music now, go head and get used to it loves."
Ashton Kutcher
Ashton Kutcher joined Two and a Half Men in season nine after Sheen's famous exit and stayed through the end of the series. He played billionaire Walter Schmidt and his character purchased Charlie Harper's house following the character's death.
After Two and a Half Men wrapped in 2012, Kutcher appeared on shows like The Ranch as well as in movies like Vengeance and Your Place or Mine. He's also a venture capitalist, having invested in companies like Airbnb and Uber.
Kutcher married his costar from That '70s Show Mila Kunis in July 2015. The two have two kids, daughter Wyatt and son Dimitri.
Conchata Ferrell
Conchata Ferrell popped up in supporting roles throughout her career, including Erin Brockovich, Network, L.A. Law and E/R (not to be confused with ER). On Two and a Half Men, she played Berta, the housekeeper, and received two Emmy nominations for her work on the CBS sitcom.
After Men ended, Ferrell appeared in Krampus, Grace and Frankie and reunited with Kutcher on The Ranch. She died in October 2020 at 77 years old.
Marin Hinkle
After the show ended, Marin Hinkle—who played Alan's ex-wife Judith— appeared in Jumanji: Welcome to the Jungle on the big screen, and on The Affair, Red Band Society, Madam Secretary, Homeland and Speechless on the small screen. She then landed the role of Rose Weissman on The Marvelous Mrs. Maisel, which ran from 2017 to 2023.
Hinkle shares a son, Ben, with her ex-husband Randall Sommer.
Melanie Lynskey
Melanie Lynskey is best known to Two and a Half Men fans as Rose, the strange next-door neighbor of the Harpers. She had a relationship with the character Charlie, and she later claimed he died in season nine. In the finale, it was revealed she kept him prisoner for four years.
Lynskey is known for her roles in films like Sadie, Little Boxes, The Changeover and Pike River plus her TV performances in shows like Togetherness, Castle Rock, Mrs. America, Candy and Yellowjackets.
Lynskey welcomed a daughter with Jason Ritter in 2018, and the couple wed two years later.
Amber Tamblyn
Amber Tamblyn joined the cast for seasons 11 and 12 as Jenny, Charlie's long-lost illegitimate daughter.
Since the end of Two and a Half Men, the Sisterhood of the Traveling Pants alum has appeared in You Hurt My Feelings, Y: The Last Man, Nostalgia, and Girlfriend's Day. She also directed and co-wrote the 2016 film Paint It Black.
Tamblyn wed David Cross in 2012 and they welcomed daughter Marlow five years later.
Holland Taylor
Holland Taylor starred in all 12 seasons of Two and a Half Men as Evelyn, Alan and Charlie's mother.
Afterwards, The Practice alum appeared in several more TV shows, including The Morning Show, The Chair, Hollywood, and Mr. Mercedes. Her list of film credits has also grown to include Motherland, Quiz Lady, The Stand In, Bombshell and Gloria Bell.
Taylor has been in a long-term relationship with Sarah Paulson.