Charlie Sheen's character on Two and a Half Men was promiscuous and racked up a list of exes over his eight seasons.
Two and a Half Men was one of the most popular shows on CBS, drawing between 13 and 16 million viewers per season. It made stars from the cast and earned a host of TV awards. The show frequently had superstar guests, who came into Charlie's life, often as a love interest.
Two and a Half Men revolved around Charlie Harper (played by Charlie Sheen), a promiscuous jingle writer whose brother, Alan Harper, and nephew, Jake Harper, move into his Malibu beach house after Alan’s wife filed for divorce. Over the first eight seasons, many famous women played Charlie Sheen's love interests, but where are they now?
16. Melanie Lynskey As Charlie's Stalker
Melanie Lynskey played Charlie's neighbor, Rose in Two and a Half Men. She had a relationship with Charlie and later became obsessed with him. She is frequently scene climbing over the balcony and into Charlie's house.
Although she is many viewers' favorite character, Lynskey has been outspoken about disliking her time on Two and a Half Men. She has revealed that the show paid her the lowest SAG fee possible and realized after the first season that her character wasn't the right role for her. The New Zealand-born actress has also spoken openly about working to change her contract.
Luckily, the actress has gone on to roles more suited to her skills. She currently stars in Yellowjackets and appeared in HBO's The Last Of Us. For her work as Shauna in Yellowjackets, she won the 2022 Critics' Choice Award for Best Actress in a Drama Series and has been nominated twice for the Emmy Award for Outstanding Lead Actress.
15. April Bowlby As Charlie Harper's Fling And Then Alan's Wife, Kandi
April Bowby plays Kandi in a recurring role in Two and a Half Men. She is first introduced in season 3 as one of Charlie Harper's flings but soon starts dating his brother Alan. Her character appears dim-witted but actually manages to get a good deal out of her divorce.
Bowlby plays Rita Farr on the show Titans and its spin-off series Doom Patrol. She has also appeared on Big Bang Theory, Mom, and You're The Worst. She appeared as Barney Stinson's obsessive ex Meg in How I Met Your Mother, and has made appearances in CSI, Psych, and CSI: NY.
14. Rebecca MacFarland As Bartender Leanne
Leanne is the bartender at Pavlov's who is there to give Charlie Harper advice on Two and a Half Men. It's hinted at throughout the show that the pair hook up. She revealed she turned her life around after waking up in Charlie's bed with a cab fare taped to her head.
She appeared in 19 Faking It episodes and in True Blood, Grey's Anatomy and Bones. Alongside acting, she is a keen mixed-media artist and shares her artwork on her social media page.
13. Lucy Lawless As Pamela
Lucy Lawless starred as Pamela in a 2005 episode of Two and a Half Men. In the season 2 episode, Charlie Harper pretends to be gay when attending a party hosted by an ad executive. While at the party, he meets Lawless' character and tries to sleep with her without the executive knowing he is straight.
Lawless is most famous for playing Xena The Warrior Princess. More recently, she has had small roles in dramas, including Top of the Lake and Burn Notice, and has lent her voice to animations like Adventure Time and The Simpsons. Recently, she has dedicated her life to charity work and ecoactivism.
12. Teri Hatcher As Judith's Sister Liz
Teri Hatcher plays Judith's sister Liz in Two and a Half Men. She makes a memorable appearance in season 1 at Jake's 11th birthday party. It also revealed that Alan asked her out before his future wife and that Liz and Charlie hooked up at their sibling's wedding reception.
Hatcher has had a long and successful career but is best known for appearing in Desperate Housewives. In recent years, she has made YouTube videos and appeared on cooking shows. She still makes brief appearances on TV shows, including Supergirl, Jane by Design, and Fantasy Island. She has a recurring role in The Odd Couple as Matthew Perry's love interest.
11. Brooke Shields As Charlie Harper's Neighbor Danielle
Brooke Shields plays Danielle in a season 4 episode, who moves next door to Charlie Harper. The pretty brunette causes a rift between the brothers who both want to date her. Although originally set up on a date with Alan by Charlie, he soon decides he is interested. The last time we see her she is falling over Jake's skateboard.
Shields recently appeared in Law & Order: Special Victims Unit 19th season, and voiced Beverly Goodman in the Adult Swim animated series Mr. Pickles and its spin-off Momma Named Me Sheriff. Shields was also the subject of the 2023 documentary, Pretty Baby: Brooke Shields, which dealt with the sexualization she felt as a young model.
10. Denise Richards As Lisa, Charlie Harper's Ex
Charlie Sheen's then-wife appeared on the show as Lisa in seasons 1 and 2. She was Charlie Harper's ex, who formally lived with him before the show until he refused to commit, and they broke up. They try to rekindle their relationship in season 2, but it doesn't work out.
Richards and Sheen have had a heavily publicized relationship after marrying in 2002. They have two children together and have had custody battles over the years. In 2018, Richards joined the cast of The Real Housewives of Beverly Hills and a year later, she joined the cast of The Bold and the Beautiful. She also regularly appears in projects on Lifetime and Christmas movies.
9. Jennifer Taylor As Charlie Harper's True Love
Jennifer Taylor's character, Chelsea, is probably one of the only women Charlie Harper has ever loved on Two and a Half Men. She appears in season 6, and her character plays a huge role in season 7 after Charlie proposes to her. Taylor actually appears in the pilot episode as the woman Jake and Charlie speak to at the grocery store, and in season 5, she stars as a woman Charlie flirts with.
Taylor has made numerous guest appearances in TV shows including Shameless, The Young and The Restless, NCIS and Burn Notice. Her most recent high-profile role was in the faith-based God's Not Dead: A Light in Darkness.
8. Jenny McCarthy As Charlie Harper's Future Stepsister
Jenny McCarthy plays Courtney Leopold, Charlie Harper's girlfriend and future step-sister in eight episodes throughout several seasons of the show. She tricks Charlie into a relationship, so she can blackmail him into buying her a Ferrari. Throughout her appearances, she asks him for money, and he later learns she is a con artist.
She later criticized Charlie Sheen for not being “upfront” about his HIV diagnosis. Sheen's team confirmed he was diagnosed after the filmed scenes together and could not have passed it on. McCarthy has more recently been known for her outspoken personality and appearances on The View. She also currently appears as a judge on The Masked Singer.
7. Katherine LaNasa As Lydia, Who Reminds Charlie Harper Of Her Mother
The former ballet dancer appeared in 4 episodes as Lydia, Charlie Harper's ex, who reminds him of his mother. On Two and a Half Men, after Charlie cancels his wedding to Mia, he dates Lydia who shares many characteristics with his mother. They have the same job, dress the same, and talk to him the same way! She falls out with Charlie's cleaner Berta, who threatens to quit her job unless he dumps Lydia.
LaNasa continues to appear on the small screen regularly. In 2016, LaNasa had a recurring role in Devious Maids and was a series regular on the Bravo's Imposters. In 2018, she played the villainous Ada in Dynasty and was a series regular on Katy Keene. Other credits include Truth Be Told, Lie To Me and Longmire.
6. Rachel Cannon As Chloe
Rachel plays Charlie Harper's ex, who leaves him for a handyman, played by Enrique Iglesias. A jealous Charlie tries to dress more youthful to win her back, but his money actually wins her over in the end.
Rachel Cannon is best known for playing Deidre in Fresh Off The Boat. She also made guest appearances in Mad Men, Major Crimes and 2 Broke Girls. She is also a savvy businesswoman and entrepreneur.
5. Jeri Ryan As The Female Version Of Charlie, Sherri
Jeri Ryan plays Charlie's villainous ex Sherri in season 2. Sherri likes to play hard to get and annoys Charlie Harper because he realizes he isn't in control of the situation. Charlie begrudgingly refers to her as the female version of himself. She later dates Alan and is one of the exes who appear at Charlie's funeral in season 7.
Jeri Ryan is best known for playing Seven of Nine in Star Trek: Voyager and more recently Picard. She has had an illustrious TV career, including roles in Dark Winds, MacGyver and Bosch. She appeared in 42 episodes of Body of Proof and 28 episodes of Shark.
4. Ming Na Wen As Judge Linda Harris
Ming Na Wen appears in both seasons 5 and 7, playing Charlie's ex Linda Harris. Her character first meets Charlie on a double date set up by Alan, but his behavior repulses her.
When Charlie is caught by the police for drunk driving, Linda is the judge on his case. Charlie likes her enough to wait, but ultimately their bedroom activity is ruined by Rose. When Charlie gets high in season seven, Linda is one of the ex-girlfriends he sees.
Ming Na Wen has had a long and illustrious career on screen and doing voice work. Many people know her from Agents of SHIELD and The Mandalorian but she has also appeared on Hacks, Fresh Off The Boat and Adventure Time.
3 Emmanuelle Vaugier As Charlie's Fiance
The Canadian actress plays Mia, Charlie's ex-fiancee on Two and a Half Men. The dance teacher first meets Charlie in season 3, where he pretends Jake loves dancing. She tries to make Charlie's lifestyle healthier, which causes a rift between them. They almost marry in Vegas but split after learning Alan won't move out.
Charlie tries to win her back over the next seasons. In season 7, she goes to Charlie with help with her singing career. He sees her during a drug-induced hallucination and she goes to his funeral in season 9. In the final episode, Mia gets a large check and an apology from Charlie.
Vaugier regularly makes guest appearances on popular TV shows like Supergirl, Magnum P.I and Mistresses. Vaugier was in a relationship with Two and a Half Men producer Chuck Lorre between 2010 and 2012.
2. Jodi Lyn O’Keefe As Satanist Isabella
Jodi Lyn O'Keefe had the recurring role of Isabella, Charlie's girlfriend, in seasons 3, 7, and 9. Isabella is a Satanist who tries to convince Charlie to join her covenant. Alan believes she has cursed him, and she tries to have a séance with Jake. She also tries to have a 'prophecy baby' with Charlie, drawing a pentagram on his stomach. She is ultimately scared away by Evelyn.
She has a lead role in VH1's Hit The Floor and played Jo on The Vampire Diaries. Her guest appearances include roles on Lucifer, Legacies and Castle.
1. Missy Pyle As Miss Pasternak
Charlie Sheen's character on Two and a Half Men, Charlie Harpere, falls for Jake's teacher, Dolores Pasternak (who is played by Pyle in all appearances, bar the last one where Alicia Witt plays her.) Charlie starts to date the 5th grade teacher after she suspends Jake for giving her the finger. She appears in season 6 as an exotic dancer after losing her job as a teacher. She believes Charlie is a gift from God and they should marry.
Pyle is a successful actress on the big and small screen. She played the coach in Jumanji: Welcome to the Jungle, and appeared in Gone Girl and Just Before I Go. Her TV work includes Y: The Last Man, season 2 of Dirty John and Impulse.