The TV sitcom Two and a Half Men was a hotbed of controversy while it was on the air, thanks in no small part to original series star Charlie Sheen. But regardless of what you think of the show or the behind-the-scenes madness, it did highlight the comedic skills of several beautiful actresses. And here’s what became of them once the show was done.
1. Melanie Lynskey as Rose
Melanie Lynskey’s Rose was Charlie’s stalker-turned-wife… and the woman who faked his death and kept him prisoner in her house for years. But even though she wasn’t the sort of person with whom you would actually want to be friends, she was an hilarious character and Lynskey put in a great performance as her.
Lynskey is still a successful actress, and she still looks great. However, she’s been open about her struggles with her body. In 2016 she told People magazine about how she had spent a long time “trying to conform to something that was not physically possible for me.” Eventually, she said, “I did have to truly become comfortable with myself, because you can’t fake it.”
2. Courtney Thorne-Smith as Lyndsey
Courtney Thorne-Smith loved being on Two and a Half Men. In 2012 she told TV show Entertainment Tonight, “It’s such an extraordinary gift to have this kind of writing. I thought by this point I’d be playing the mom and always shouting, ‘Hey kids!’ To get to play this great, funny, sexy, drunk, crazy character is incredible.”
These days, Thorne-Smith is playing Emma Fielding in the Hallmark Movies & Mysteries franchise of the same name. And ironically, considering her past comment about casting, she’s also on a show called Mom, which happens to involve a lot of the same crew members that Two and a Half Men did.
3. Judy Greer as Bridget
Judy Greer actually played two roles on Two and a Half Men. When Charlie Sheen was on the show she played Myra, one of his many romantic interests. But when the show was revamped and Ashton Kutcher was brought in, Greer was cast in the recurring role of his ex-wife Bridget.
Greer continues to be one of the most prolific and sought-after character actresses in the business. She’s been in movie blockbusters including Jurassic World and Ant-Man. She also wrote a book titled I Don’t Know What You Know Me From: Confessions of a Co-Star!, but plenty of people will know her primarily for Two and a Half Men.
4. Sophie Winkleman as Zoey
British actress Sophie Winkleman played a love interest of Walden’s, the magnificently named Zoey Hyde-Tottingham Pierce. She was almost Walden’s wife until it transpired she’d been cheating on him. There was a joke in the show about Zoey being a duchess in her homeland – and that’s actually a nod to Winkleman’s real life.
Winkleman holds the official title of Lady Frederick Windsor. She’s the wife of Lord Frederick of Windsor, the son of the Queen’s first cousin. She has two children with him as well, daughters named Isabella and Maud. And despite her being a member of the British royal family, she’s continued to act. Perhaps Meghan Markle could seek her advice?
5. Jennifer Taylor as Chelsea
Chelsea Melini, played by Jennifer Taylor, was another beautiful woman in Charlie’s never-ending line of them. She managed to become his fiancée for a little while, though, after he realized he was genuinely in love with her. Alas, it didn’t work out, and Charlie ended up dating her best friend instead.
Taylor has added more roles to her CV since then, but she thinks fondly of Two and a Half Men. In a 2018 interview with Jeremy Roberts she called it “one of the best things that ever happened to me” and said of Chelsea, “There’s a lot of me in her because she was pretty no-nonsense.”
6. Jeri Ryan as Sherri
Jeri Ryan was already famous for playing Seven of Nine on TV sci-fi drama Star Trek: Voyager before she was cast as Sherri on Two and a Half Men. Sherri was one of Charlie’s more memorable girlfriends – she was very much like him in many ways. But then they broke up, and she started seeing Alan instead.
Ryan is still a famous actress, but that’s more because of Star Trek rather than Two and a Half Men. In 2020 she reprised her role of Seven of Nine in Star Trek: Picard, to the delight of fans. That same year she appeared in the rebooted TV show MacGyver as well. She’s definitely keeping busy.
7. Missi Pyle as Ms Pasternak
Character actress Missi Pyle played Dolores Pasternak, Jake’s ex-stripper schoolteacher. She had a memorable run on the show: first she suspended Jake, then she started dating Charlie who persuaded her into favoring Jake instead, and then she got dumped by him. That’s life in a sitcom for you.
In 2016 Pyle remembered her time on the show to website The AV Club. She said, “It was just a fun little character to play, and then four years later, they ask me to come back to do an arc, but I got offered a Broadway show. I just felt like I had to do the Broadway show, so I ended up not being able to do that arc.” She still maintains a very successful career.
8. Heather Locklear as Laura
Melrose Place star Heather Locklear played Laura in Two and a Half Men, Alan’s divorce lawyer with whom Charlie quickly became enamored. But as soon as he began neglecting her, she changed the divorce settlement, and things ended amusingly badly. In real life, however, Locklear and Charlie Sheen are friends.
In fact, Locklear came out in support of Sheen after he went public with his HIV diagnosis in 2015. She wrote on her Instagram account, “My heart hurts. Prayers for Charlie and his family.” Locklear continues to make headlines for various controversies, some even including another Charlie Harper ex, Denise Richards.
9. Denise Richards
Denise Richards married Charlie Sheen in 2002 and had two kids with him, so it seemed a sweet idea for her to cameo on Two and a Half Men as one of Charlie’s exes. But then she became his ex in real life when she filed for divorce in 2005. Since then their relationship has been complicated to say the least.
Richards is now married again, to healing center CEO Aaron Phypers, and told Us Weekly magazine in May 2020 that she had reached an amicable co-parenting agreement with Sheen. She was also on the reality show Real Housewives of Beverly Hills until 2020, when she made her exit amid a storm of controversy.
10. Ming-Na Wen as Linda
Ming-Na Wen’s Linda was another romantic interest for Charlie, and they met under awkward circumstances. Firstly they encountered each other on a difficult double date and then later on Charlie was hauled in front of a judge for a DUI and it turned out to be Linda. Needless to say, the relationship didn’t work out.
But Wen has done a lot more than just Two and a Half Men. She was the voice of Mulan in Disney’s animation of the same name, she was in ER and Agents of S.H.I.E.L.D. to name just two shows – and she also happens to be in her 50s now. But she absolutely doesn’t look it.
11. Paget Brewster as Jamie
Paget Brewster’s character Jamie Eckleberry followed an old comedy trope. She was the overweight girl from high school who Charlie and Alan picked on and bullied – but then she reappeared as an adult looking thin and gorgeous. Charlie and Alan both tried to get her attention, but she unsurprisingly turned them both down.
Brewster has done plenty of high-profile work since Two and a Half Men, including the TV shows Community and Criminal Minds plus voice work on American Dad and DuckTales. She’s also embraced aging – her hair began turning grey in 2019, and she posted pictures of it to her social media account.
12. Brooke Shields as Danielle
The famously beautiful Brooke Shields has had a complicated, fascinating life in showbiz, and a role in Two and Half Men is just a small part of it. She played a girl-next-door, Danielle, in Season Four of the show. Charlie and Alan fought over her, but neither of them got her in the end.
Shields has done plenty of work since then. She played the mother of Miley Cyrus – who was also a Two and a Half Men guest star – in the Hannah Montana movie. And in 2014 she published a book in order to set the record straight about her life as a child star.
13. Jenny McCarthy as Courtney
Jenny McCarthy was already a big name before she starred in Two and a Half Men. She was a former Playboy model whose face was a familiar one on TV. On Two and a Half Men she played another blonde bombshell, Courtney Leopold, a trickster who dated Charlie but also took all his money.
Jenny McCarthy is still on TV a lot: she’s been on The View, The Masked Singer and also happens to be married to Donnie Wahlberg. There was a reality TV show documenting their relationship, too. But McCarthy is now more infamous than famous since she’s a vocal leader of the dangerous anti-vaccination movement.
14. Jenna Elfman as Frankie/Dharma
Jenna Elfman was actually on Two and a Half Men twice, once in 2004 and again in 2011. The first time around she played Frankie, a car-smashing woman over whom Charlie and Alan fought. But on her return she played Dharma, her character from the TV show Dharma and Greg, in a crossover.
Both Dharma and Greg and Two and Half Men are gone from the schedules now, but Elfman has plenty else to occupy her. She played Naomi on Fear the Walking Dead, the successful spin-off zombie show The Walking Dead and also made an appearance in the rebooted version of The Twilight Zone.
15. Hilary Duff as Stacey
Ex-child star Hilary Duff announced via Twitter that she would be playing a role in Two and a Half Men. She tweeted on April 2, 2013, “So excited to be joining the cast of Two and a Half Men this week! I get to play a crazy drunk girl, funnnn!!!” This was an appropriate way to announce her character, who turned out to be a phone-obsessed date.
Duff isn’t as big as she was in her teenage years, but she’s maintained a pretty steady career since becoming an adult. Guest appearances such as her Two and a Half Men one helped a lot with that, of course. And there may yet still be a reboot of her smash-hit TV show Lizzie McGuire one day.
16. Teri Hatcher as Liz
Back in 2004 before the phenomenon that was Desperate Housewives made her a household name, Teri Hatcher appeared on Two and a Half Men as Liz. Liz was the sister of Alan’s ex-wife Judith, and she caused a whole lot of chaos among the main characters, but she only ever appeared in one episode of the show.
Desperate Housewives was a big deal for Hatcher, and ever since it finished she’s faded from the spotlight a bit. She’s constantly dogged by rumors that she’s difficult to work with, which can’t help matters at all. Her most recent high-profile role was in the show Supergirl, but that didn’t last long either.
17. Mila Kunis as Vivian
Just after Mila Kunis and Ashton Kutcher announced they were engaged, it also came out that Kunis would be appearing opposite her new fiancé on Two and a Half Men. She would play a beautiful young woman with whom Kutcher’s Walden fell in love just as he was supposed to be proposing to his girlfriend.
Kunis and Kutcher packed the episode full of references to their real-life relationship – there was even one about That ’70s Show, in which the two famous actors were co-stars prior to falling in love. Though Vivian and Walder might not have stayed together, Kunis and Kutcher did, and they’re parents to two kids now.
18. Miley Cyrus as Missi
Former Disney star Miley Cyrus appeared on Two and a Half Men in 2012 when she was a 20-year-old. She was playing the very attractive Missi, and it seemed like a bit of an attempt to shed her previously wholesome image. She showed up in a bikini and flirted with the guys.
Cyrus’ attempts to seem more grown-up only got wilder from there. At the 2013 MTV Video Music Awards she took part in some very sexual routines on stage, shocking audiences who remembered her from her Hannah Montana days. She’s calmed down a bit since, but she’s still known as a bit of a wild child.
19. Megan Fox as Prudence
Before she shot to fame with the Transformers movies, Megan Fox popped up in a guest role on the very first season of Two and a Half Men. She played Prudence, the young granddaughter of Charlie’s housekeeper Berta. It must have been obvious to many at that point that she was only a step away from megastardom.
Fox is considered to be one of the best-looking women in the entire world. She’s spent a long time fighting to get out of the box Hollywood put her in, though. These days she accepts roles which have substance to them and has expressed anger about being portrayed as a feeble airhead in her earlier days.
20. April Bowlby as Kandi
April Bowlby played one of the most memorable romantic interests on Two and a Half Men. She was the beautiful but not particularly bright Kandi, a woman for whom Alan falls. She married him in Las Vegas only to divorce him before too long; however, she and Alan remained friends after the fact.
Bowlby continued to pop up on Two and a Half Men right up until it ended in 2015. For a while she did guest roles on TV shows such as The Big Bang Theory, but come 2019 she became part of the DC television series Doom Patrol, playing Rita Farr. It was a massive success with critics.