Charlie Sheen
Charlie Sheen 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. Sheen entered drug treatment and the eighth season was cut short.
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, Sheen popped up on The Goldbergs and on the big screen was in Scary Movie 5, Machete Kills and 9/11.
The dad of five came out as HIV positive in 2015.
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.
Cryer released a book about his career in show business and has popped up on Mom, The Ranch, NCIS, Robot Chicken and Lady Dynamite among others.
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 voiced his desire to leave the series after forging down a religious path in real life. Jones eventually left the series, but returned for the series finale in 2015.
Jones attended University of Colorado Boulder after leaving the sitcom and eventually joined and entertainment company with Sean Combs' son, Justin Combs. His last credited acting role is in Louis C.K.'s Horace and Pete in 2016.
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.
Since the end of Men in 2012, Kutcher voiced himself on Family Guy, appeared on Shark Tank and jumped to Netflix as an executive producer and star of The Ranch. He also reprised his That '70s Show role in the recent That '90s Show. He married 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
Marin Hinkle played Alan's ex-wife, Judith, on Two and a Half Men.
After the show ended, she 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 also starred in Amazon's Emmy-winning series The Marvelous Mrs. Maisel.
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 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 quite active on the big screen, with roles in Sadie, Little Boxes and The Changeover. On TV, she appeared in Girlboss, Wet Hot American Summer: Ten Years Later, Summer Camp Island, Castle Rock and, most recently, Showtime's Yellowjackets.
Amber Tamblyn
Amber Tamblyn joined the cast for seasons 11 and 12 as Jenny, Charlie's long-lost illegitimate daughter.
In 2016, she directed and co-wrote Paint It Black and since the CBS comedy ended, she appeared on Community, Comedy Bang! Bang!, Lip Sync Battle and Drunk History.
Holland Taylor
Holland Taylor starred in all 12 seasons of Two and a Half Men as Evelyn, Alan and Charlie's mother.
Taylor has been quite active since Men ended, appearing in Mr. Mercedes, The Orville, Speechless and Good Behavior.