Part of the appeal of Two And A Half Men was always its hot guest stars. A steady parade of girlfriends, ex-girlfriends, one-night stands, flirty strangers, teachers and foils marched through the show’s 12-season run. It would be hard to find an episode (there were 262 in total) that didn’t feature a guest appearance by a hot actress.
While one of the show’s title characters was a kid, the series was driven in large part by sex appeal. That’s one of the reasons the kid – played by Angus Jones, a devoted Christian – eventually left the show, claiming moral disagreement with the series.
For eight seasons, the program was propelled by Charlie Sheen‘s persona, drawing comedy out of his hedonistic character (not coincidentally named “Charlie”) and the clash with his straight-arrow brother Alan, played by John Cryer. Eventually, Sheen’s persona overpowered the show and he forced himself off in very public dispute/meltdown (WINNING!). The final four seasons featured Ashton Kutcher as a replacement (his character, Walden, moved in with Alan), but the show’s general tone had been established. Now, with the sheer number of sexy guest actresses, to make this list, it is not enough to be beautiful. Special points are given for that something special – actresses that are a cut above the usual “Hot Girl at Party #3.” These actresses are talented, funny and accomplished, along with also being outrageously attractive.
14. Jenny McCarthy
Before she was a daytime talking head and the face of the vaccines-cause-autism movement, Jenny McCarthy was actually known as a working Hollywood actress. During this period of time, before her appearance on The View and before her marriage to Donnie Wahlberg, she was also considered one of the hottest of working Hollywood actresses, a star who began a career in Playboy and made her name through a series of comic/sexy appearances on TV and in movies. Two and a Half Men marked the tail end of this period. McCarthy appeared in eight episodes total, starting in season five and lasting until season nine. She plays a con artist and love interest for Charlie.
13. Teri Hatcher
Teri Hatcher came to prominence as one of the title characters in the 1990s superhero romance Lois & Clark: The New Adventures of Superman. Her career sputtered a bit after the show was cancelled in 1997, but revived when she was cast as the girl-next-door beauty on Desperate Housewives. It was while this hit show was ramping up that Hatcher appeared in a first season episode of Two and a Half Men. She appeared as the sister of Alan’s first wife. A competitive streak almost pushes her to sleep with Alan, while her sister makes a move on Charlie. In the end, both of the women bail out of their encounters.
12. Hilary Duff
Hilary Duff made her name as a child actress on the Disney TV show Lizzie McGuire. After the show was cancelled in 2004, she worked steadily in forgettable movies and in guest spots on TV series, such as Joan of Arcadia, Ghost Whisperer and Community. This run included an episode in Two and a Half Men‘s tenth season. Duff plays Stacey, a younger girlfriend of Walden. He eventually ditches her in favor of her grandmother, played by Marilu Henner.
11. Miley Cyrus
The title of the show is Two and a Half Men. Most of the women on this list play love interests to the two full men in the title. Miley Cyrus is an exception. She plays a love interest for Jake (the title’s half-man). At the time, Cyrus, who was not yet 20 years old when she appeared on the show, was in the middle of transitioning from squeaky-clean Disney starlet – star of the Hannah Montana franchise – to a more adult performer. She appeared on two episodes in season 10. The episodes aired in 2012, shortly after the release of Cyrus’ movie LOL. A year later, the actress and singer would become a lightning rod for controversy when her twerking appearance on the MTV Music Awards generated a torrent of internet scolding.
10. Brooke Shields
Brooke Shields might be the biggest name that has ever appeared on a one-episode stint on Two and a Half Men. This is especially true early in the run. Shields rose to prominence in the late 1970’s and 1980’s as a model and early film appearances in movies like Pretty Baby and The Blue Lagoon. These movies were extremely sexually explicit given that she was teenager at the time. The roles made Shields an early, if somewhat uncomfortable, sex symbol. By the time she appeared on Men, in an episode in season four, Shields’ sitcom, Suddenly Susan, had been over for several years and her star had dimmed. On the episode, she plays Danielle, a girl that is set up on a date with Alan but ends up causing friction between the brothers.
9. Missi Pyle
A busy actress who has never had that one breakout role, Missi Pyle has appeared in a string of sexy/funny roles in movies and on TV. Her film credits include Dodgeball, 50 First Dates and Harold & Kumar Escape from Guantanamo Bay. On TV, she has appeared on Friends, Frasier and (more recently) Inside Amy Schumer and The Mindy Project. Pyle first appeared on Two and a Half Men in its second season as Miss Pasternak, Jake’s teacher and a love interest for Charlie. The character also appeared several times later in the show, including an episode in season six where Miss Pasternak was recast with a different actress (more on that later in the list).
8. Judy Greer
Chuck Lorre must really like Judy Greer. After her first appearance in the show’s fourth season, the series’ creator brought her back, eventually having her play two other characters, bringing her total character count to three. And who can blame Lorre? Greer is one of the top girl-next-door best-friend actresses around. She’s so well-known for not being quite well known that she wrote a book called I Don’t Know What You Know Me From: Confessions of a Co-Star. Greer first appeared in a two-episode stint as one of Charlie’s short-lived girlfriends. The actress returned in season nine in a more substantial role as Walden’s ex-wife, Bridget. As a kicker, Greer did semi-cameo in season nine as a lesbian who looks a lot like Bridget.
7. Allison Janney
Allison Janney is a different type than most of the other names on this list. True, she’s not a sexpot, but she’s still a stunner in her own way. In addition, she gets extra credit for having some of the best overall acting chops of any of the series’ guest stars. Janney appeared in a season four episode as a woman Alan met on dating site. The character turns out to have some quirks, such as tying him to the bed and leaving him there. At the time, Janney was best known for her role on The West Wing, which had recently ended when her episode aired. Apparently, her guest spot was a memorable one, at least for Two and a Half Men creator Chuck Lorre. Janney currently stars on Mom, which was co-created by Lorre.
6. Paget Brewster
Until she finally caught on as a lead role on the crime thriller series Criminal Minds, it seemed as if the talented Paget Brewster would be a permanent guest star. She began her career strong, with a six-episode guest spot on Friends, but quickly settled into a series of one-off roles and leading stints in doomed short-lived series. Part of that run was an appearance in the second season of Two and a Half Men. Brewster played an old childhood friend of Charlie and Alan’s who was once a plain-Jane but had blossomed into a sexy temptress. In the episodes, she leads on both the main characters before finally leaving them both flat.
5. Denise Richards
When Two and a Half Men started, Charlie Sheen was married to an actress who was almost universally acknowledged as one of the hottest in Hollywood: Denise Richards. With Sheen trying to get his new series off the ground, it’s no surprise that he asked his famous wife for a guest spot. Richards appeared in the tenth episode of the series as a former flame who is getting married to another man. She returns for a second appearance in season two. Over the next few years, it seemed like happy times for Sheen and Richards as they had two children and Two and a Half Men became one of the most popular series on TV. However, by 2006, Richards had filed for divorce. Sheen’s life would get increasingly complicated from there, eventually culminating in his high profile departure from the show in 2011.
4. Ming-Na Wen
Ming-Na Wen has had a busy Hollywood career, starting with her first breakout role in The Joy Luck Club and including providing the voice of the heroine in Disney’s Mulan franchise. She is best known for a long run on ER, though in recent years, her most high-profile role has been on Agents of S.H.I.E.L.D. In between, she had an extended guest spot on Two and a Half Men. She appeared in 5 episodes, starting in the fifth season. Wen appeared as a judge who goes from overseeing Charlie’s drunk-driving hearing to becoming his girlfriend. She eventually breaks up with him after he publicly embarrasses her.
3. Alicia Witt
Alicia Witt is an underrated actress. She was a child actress in the movie Dune and has worked steadily since the early 1990s, including memorable guest spots on The Sopranos and on Justified. On Two and a Half Men, Witt spent one episode as Miss Pasternak, taking over the role from Missi Pyle. Early in the show, Charlie dates Miss Pasternak, Jake’s teacher, but eventually dumps her. In Witt’s season six appearance, Miss Pasternak has lost her teaching job and has taken a gig as a stripper (well, technically, she’s working in a bikini club), under the name Desiree Bush. Charlie and Alan ask her to move in with them, leading to all the hilarity you’d expect.
2. Megan Fox
Megan Fox is generally considered one of the most beautiful actresses of her generation. Her acting skills have occasionally been in doubt, but when your biggest break comes as a human prop in a giant-robot-explosion movie, it’s safe to say you’re not being asked to do much. While Fox has become a major Hollywood sex symbol over the last decade, credit has to go to Two and a Half Men for realizing the potential early. Fox’s appearance took place way back in season 1, well before Transformers and before she began her run on the TV show Hope & Faith. In fact, the episode aired in January 2004, before Fox had even turned 18, and about 6 weeks before the release her first real movie role in Confessions of a Teenage Drama Queen.
1. Mila Kunis
It’s not a surprise that the hottest guest performer in the history of Two and a Half Men would be the finance of the show’s star. Well, it might have been surprising if the hottest guest star in the show’s history had been Jon Cryer’s finance. But it’s not surprising that Mila Kunis, then engaged to Ashton Kutcher, would top the guest-star rankings. The star of That 70s Show and Forgetting Sarah Marshall appeared in a season 11 episode as a traveler who makes Walden question whether he really loves his girlfriend. Since the appearance, which aired in April, 2014, Kunis and Kutcher have gotten married and had a daughter. Kunis had announced the pregnancy just 3 weeks before her guest spot aired.