Playing out like a modern-day Odd Couple, Two and a Half Men charmed viewers with the ongoing antics of hedonistic bachelor Charlie (Charlie Sheen), who gets saddled up with his high-strung brother Alan (Jon Cryer) and his nephew Jake (Angus T. Jones) after Alan’s divorce.
Over 12 seasons, the hit CBS sitcom found massive success, scoring 40-plus Emmy nominations, including Outstanding Comedy Series, and helped Cryer win in his respective category. But for a while, the off-screen drama stole the spotlight, causing one and a half of the original men to leave.
After name-calling Men creator Chuck Lorre, demanding a raise despite being the then-highest-paid TV actor, and conducting bizarre interviews (remember “Tiger Blood?”), Sheen was fired and replaced by Ashton Kutcher for the final four seasons. But some grudges don’t last forever in Hollywood, as Lorre and Sheen have reportedly reconciled and united on the Max series, Bookie.
Join Entertainment Weekly as we look back at the Two and a Half Men cast to see where they are now.
Charlie Sheen (Charlie Harper)
Like his brother Emilio Estevez, Charlie Sheen followed the footsteps of his famous father Martin Sheen right into an acting career. He first emerged in ensemble films like Platoon (1986), Young Guns (1988), and Eight Men Out (1988) before starring in the 1991 action movie spoof Hot Shots! (and 1993’s Hot Shots! Part Deux), which also featured his future Two and a Half Men sibling Jon Cryer.
Other notable Sheen film appearances include Wall Street (1987) with his father, The Three Musketeers (1993), the Major League movies (1989, 1994), and the Scary Movie franchise (2003, 2006, 2013). In 2000, Sheen began filling in for Michael J. Fox on the ABC political sitcom Spin City — playing the first of many characters named Charlie — and took to the medium so well that his follow-up role on Two and a Half Men brought him success… until his well-documented railing got himself fired.
“There are a lot of great memories [on Two and a Half Men]. Years of great memories, when we were cooking with gas and we were delivering something that people were really invested in, really enjoying, and were really connected to,” Sheen told Deadline while looking back on the series in December 2023. “I mean, we were working really hard on that show, in every aspect of the production, from the writers room to the crew, to the cast. Everybody. We knew what we had, and the value of taking the time to create it properly.”
Sheen left the show in 2011 after 178 episodes and quickly went on to star on Anger Management, which ran for three seasons on FX. Since then, he’s made a few TV guest appearances, including his two-episode stint on Bookie with his old boss, Chuck Lorre.
Sheen has five children, including two with ex-wife Denise Richards, and two with ex-wife Brooke Mueller.
Jon Cryer (Alan Harper)
Prior to Men, Jon Cryer was best known for his portrayal as the offbeat Duckie in the 1986 John Hughes teen movie Pretty in Pink, which he followed with not-quite-as-successful teen movies like Morgan Stewart’s Coming Home (1987) and Hiding Out (1987). He also appeared in the 1987 film Superman IV: The Quest for Peace. Additionally, he starred and wrote a few movies — The Pompatus of Love (1996) and Went to Coney Island on a Mission from God… Be Back by Five (1998) — and had TV roles on the series Partners, Getting Personal, and The Trouble With Normal before finding a long-term gig with Two and a Half Men.
Being the only main cast member to stay throughout all 12 seasons of Two and a Half Men, Cryer wound up winning two Emmys for his work on the seminal series: Outstanding Supporting Actor in a Comedy Series in 2009 and Outstanding Lead Actor in a Comedy Series in 2012. Reflecting on his former costar’s 2011 breakdown, Cryer told The View in 2024, “[Charlie Sheen] blew it up… I wish him the best, he should live in good health for the rest of his life, but I don’t know if I want to get in business with him for any length of time.”
Post Men, Cryer’s most prominent role has been Lex Luthor, who he has portrayed on the CW Arrowverse series like Supergirl, The Flash, and Batwoman. In 2015, he released a memoir, So That Happened. Since December 2023, he stars alongside Abigail Spencer on the NBC sitcom Extended Family, in which he plays a man who cohabitates with his ex-wife (Spencer) to raise their kids post-divorce.
Cryer has two children, one with wife Lisa Joyner, and one with ex-wife Sarah Trigger.
Angus T. Jones (Jake Harper)
Like Charlie Sheen, Angus T. Jones eventually derided the series that had made him a star. The then-child actor had made a few movies like See Spot Run (2001), Dinner With Friends (2001), The Rookie (2002), and Bringing Down the House (2003) before getting cast on Men at 10 years old — becoming the most well-paid child actor in TV with an eventual salary of $350,000 an episode.
In 2012, then-19-year-old Jones made a video for a Christian group in which he pleaded with people to stop watching the show, saying: “I’m on Two and a Half Men, and I don’t want to be on it. Please stop watching it and filling your head with filth.” He left the show soon afterward. Jones later apologized for his rant and made a brief appearance on the series’ generally low-regarded two-part finale.
He appears to have left the entertainment industry after Men, with only two additional credits to his name: Horace and Pete and Bookie, the latter marking a Men reunion with Sheen and Chuck Lorre.
