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
12 Hilary Duff
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
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
7 Allison Janney
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
2 Megan Fox
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.