'Two and a Half Men': These Were The Best Guest Stars

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'Two and a Half Men'

While Two and a Half Men is loved to this day for its main cast, the show is also well-known for its hilarious and random guest stars. Many of these A-list actors portrayed love interests for "Charlie," "Alan," and "Walden," but some filled regular roles on the popular sitcom too. From TV icons to the cast's off-screen partners, Two and a Half Men welcomed many unforgettable guest stars. Find out the very best ones in this gallery!

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#11: Mila Kunis

Ashton Kutcher welcomed a special visitor when his wife Mila Kunis guest starred in season 11. She played "Vivian," with whom "Walden" grows infatuated. Ironically, Kutcher's off-screen partner rebuffs his advances in the episode!

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#10: Gary Busey

Gary Busey made a brief but memorable cameo in Two and a Half Men season 9. The colourful actor appeared as a psych-ward patient next to "Alan" when he's hospitalized following a breakdown over the death of "Charlie."

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#9: Denise Richards

It was a family affair on Two and a Half Men when Denise Richards guest starred in seasons 1 and 2. Charlie Sheen's off-screen wife portrayed "Lisa" on the sitcom, a girlfriend and ex of "Charlie Harper." He tries to win her back after learning she's getting married, only to still find himself unable to commit to a relationship. The married couple also split in real life in 2005, a few years after Richards guested on Two and a Half Men.

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#8: Cloris Leachman

TV royalty Cloris Leachman was among the many icons to guest star on Two and a Half Men. She memorably played "Norma," an elderly neighbour of the "Harpers," with whom both "Alan" and "Charlie" get romantically involved.

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#7: Sean Penn

Sean Penn brought star power to Two and a Half Men's season 2 premiere. The actor appeared as himself, along with Elvis Costello and Harry Dean Stanton, as a member of an exclusive support group that "Charlie" belongs to. "Alan" desperately wants to join the group — but he doesn't turn out to be a great fit.

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#6: Ming-Na Wen

Two and a Half Men fans really wanted "Charlie Harper" to clean up his act when he dated "Linda" in season 5. She was a judge who demanded that "Charlie" respect her. Actress Ming-Na Wen played the part, but "Charlie" of course blows it by embarrassing her at an awards ceremony.

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#5: Jason Alexander

Seinfeld star Jason Alexander made a return to TV comedy in Two and a Half Men season 9. In the show's 200th episode, he played "Dr. Goodman," the oddball doctor of "Alan Harper" who treats him following a heart attack.

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#4: Jenny McCarthy

Actress and model Jenny McCarthy captivated Two and a Half Men fans in several episodes across seasons 4 and 5. She played "Courtney" AKA con artist "Sylvia," another of the many short-lived relationships for "Charlie Harper." Despite "Courtney" trying to scam him, "Charlie" couldn't help but be drawn to the former Playboy model.

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#3: Arnold Schwarzenegger

Arnold Schwarzenegger was one of many surprises in Two and a Half Men's series finale in season 12. "The Terminator" himself appeared as "Lt. Wagner" in the show's last episode, hearing "Alan" and "Walden" recount fears of "Charlie Harper" returning to seek vengeance. Christian Slater and John Stamos also made cameos in the bizarre yet unforgettable finale.

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Two and a Half Men fans kept up with the sitcom over the years due to the chemistry between cast members Charlie Sheen, Jon Cryer, and Angus T. Jones (and, later, Ashton Kutcher). But another part of the show's charm came in the performances of many guest stars over its 12-season run, which fans continue to enjoy in reruns today.

Two and a Half Men: The Best Guest Stars

Of course, womanizer "Charlie Harper" dated dozens of women—many of them short-lived guest stars—during his seasons as a cast member. But "Alan," "Walden," and even "Evelyn" were in relationships with partners played by A-list guest stars.

At other times, popular celebs made cameo appearances on Two and a Half Men, drawing laughs for the randomness of their presence (like Gary Busey). Others, such as Michael Clarke Duncan, Jason Alexander, and even Arnold Schwarzenegger, filled general roles on the sitcom over the years. The cast's off-screen partners even made more than a few appearances on the show, too.

Two and a Half Men aired for 12 seasons and a total of 262 episodes before it concluded in 2015. Find out the show's very best guest stars in our gallery!