Contents
- 20. Laura (Heather Locklear)
- 21. Paula (Paula Marshall)
- 22. Donna (Kimberly Quinn)
- 23. Gabrielle (Justine Eyre)
- 24. Ms. McMartin (Maggie Lawson)
- 25. Berta (Conchata Ferrell)
- 26. Courtney (Jenny McCarthy)
- 27. Liz (Teri Hatcher)
- 28. Tammy (Jaime Pressly)
- 29. Olivia (Krista Allen)
- 30. Cindy (Kristin Dattilo)
- 31. Kate (Liz Vassey)
- 32. Jamie (Paget Brewster)
- 33. Rachel Cannon as Chloe
20. Laura (Heather Locklear)
Healthier Locklear played Laura, Alan’s divorce attorney, while Alan and Judy were splitting up. Charlie tried courting her but seriously messed up after promising to make himself available to her at all times—a promise he couldn’t keep. Classic Charlie!
While she was a successful actor in her own right, Heather went through a very public divorce herself after the show, which compounded her health and took her away from the screen. She’s been in several shows since—Tyler Perry’s Too Close To Home and Franklin & Bash to name a few.
21. Paula (Paula Marshall)
Check out that imaginative name again! Maybe the show’s executive producer Chuck Lorre gives his female characters names whenever he needs to remember a new housekeeper. Otherwise, they seem to just go on their own. Paula was Alan’s love interest on the show.
She’s a married mom of one, wedded to another actor, Daniel Nucci. She’s appeared in a few hit shows, including House, Law and Order, The Mentalist, Switched at Birth, and Murder in the First.
22. Donna (Kimberly Quinn)
Just another one of Alan’s love puppets. After he got bored of Donna, played by Kimberly Quinn, Alan asked Charlie for advice on how to dump her without hurting her feelings. Needless to say, she got very upset! Whoopsie!
Outside the show, she’s an accomplished actor and director. She co-produces films with her husband, Theo Melfi, and has worked on projects with big stars like Jessica Alba and Tim Allen. As well as acting and directing, Kimberly also produces and writes. She’s an all-around talent machine!
23. Gabrielle (Justine Eyre)
After finding out that Charlie had denied him a woman in high school, Alan sought to get revenge by stealing his current property. He decided to take Gabrielle, Charlie’s then-girlfriend, for himself. Charlie gets upset, and Alan tells him he can have her back.
The beautiful Justine Eyre is both an actor and a model, and she’s been in a few other shows that you might recognize, including The Secret Life of the American Teenager, CSI: Miami, and Mad Men.
24. Ms. McMartin (Maggie Lawson)
When Alan and Walden decide to adopt a child, Ms. McMartin, played by Maggie Lawson) is sent to see if their home is a good environment to raise a kid in. Of course, Alan and Walden lie about their lives and home, and as a result, they lose their chance to adopt.
Maggie Lawson is no stranger to sitcoms. She starred in Inside Schwartz, Crumbs, and It’s All Relative, and she’s been in other shows such as Angel From Hell, The Great Indoor, and Psych. Needless to say, she’s had quite a successful career.
25. Berta (Conchata Ferrell)
This is probably one of the few women on the list that Charlie didn’t try to date. The hardworking housekeeper, Berta, played by Conchata Ferrell, always offers up her quick wit and gets laughs from the audience. She gets a kick out of seeing the boys struggle and squirm.
As a character actor, she’s received two Emmy award nominations. While she’s mostly been a main player on Two and a Half Men, she also had a part on Netflix’s The Ranch and other projects, and she starred in the crime-noir movie, Deported.
26. Courtney (Jenny McCarthy)
You can’t con a conner. Courtney, played by Jenny McCarthy, was in and out of Charlie’s life. During the course of the show, this so-called “former” con artist manages to make off with over $500,00 and Charlie’s Ferrari. In the end, it turns out that Courtney (whose real name is Sylvia) was working on behalf of her con artist mom and dad. What a twist!
This former playmate is an actor, television host, and author. She’s most well known these days for espousing dangerous and disproven ideas about vaccines. McCarthy now holds a spot on The Masked Singer as a judge.
27. Liz (Teri Hatcher)
This iconic actress has been known for two major television roles: first as Lois Lane on Lois & Clark: The New Adventures of Superman and as Susan on Desperate Housewives. She appeared on Two and a Half Men as Judith’s “sleazy” sister.
She finally got her breakthrough after appearing on Seinfeld, and from 2005 to 2009, she won a Golden Globe for her work on Desperate Housewives, as well as three Screen Actors Guild Awards and a Primetime Emmy nomination for Outstanding Lead Actress.
28. Tammy (Jaime Pressly)
Although her arms are covered in tattoos, Tammy, played by Jaime Pressly, is a soft and sweet soul. She played Jake’s girlfriend, but she might have been old enough to be his mother. Tammy had three kids of her own in the show, one of which Jake slept with, which is a psychotic thing to do if you ask us.
Jaime went on to do quite well for herself in Hollywood. With a Golden Globe and a Screen Actors award under her belt, as well as two Emmy Award nominations, she has nothing to prove. She’s best known for her work in The Oogieloves in the Big Balloon Adventure as Lola.
29. Olivia (Krista Allen)
Olivia, played by Krista Allen, is one of Charlie’s ex-girlfriends. She only had a brief appearance on the show when, discussing her and Charlie’s relationship, she splashed a drink all over Charlie’s shirt, humiliating him.
In real life, Krista is a stand-up comedian and well-known actress. She’s known for her work in Hollywood movies such as Anger Management and Final Destination, as well as her work on TV in Baywatch and Days of Our Lives.
30. Cindy (Kristin Dattilo)
As someone that actually rejected Charlie, Cindy, played on the show by Kristin Dattilo, is something of an outlier to the other women on this list. Her rejection sent Charlie into a period of terrible longing. As one of his first crushes—perhaps this explains why Charlie is so on the lookout to beat down affection, having been unable to get the girl he wanted.
Other than taking a little break to raise her kids, Kristin has pulled out an unstoppable career in the entertainment industry with appearances in such shows as Friends, The Chris Isaak Show, CSI: Crime Scene Investigation, 90210, Dexter, Veronica Mars, and Beverly Hills.
31. Kate (Liz Vassey)
Charlie met Kate, played by Liz Vassey, at Jake’s soccer game, and the two hit it off. She meets him later, as a different character, in a hilarious scene in which Charlie needs a mole removed from his behind. Guess who walked into the doctor’s office?
After that debacle, it’s easy to see why Charlie might get shy. After her appearance on Two and a Half Men, she worked on CSI: Crime Investigation as Wendy Simms. She stayed on CSI for five years. She also worked on a web series called Nikki and Nora.
32. Jamie (Paget Brewster)
Paget Brewster played Jamie, the kid that Charlie and Alan had bullied in school. They called her names, like Eckleberry hound. All that changed when they found out that she was attractive, however. Of course, then they tried to hit on her, but naturally, she knocked them both back.
She found her niche on the CBS crime drama Criminal Minds as Special Agent Emily Prentiss. Her most recent work was The Witch Files. Her last work in films was the spooky The Witch Files movie and Hypochondriac. She’s also set to star in How I Met Your Father, the sequel to the popular How I Met Your Mother series.
33. Rachel Cannon as Chloe
Who remembers this crazy scene? After dumping her because he felt Chloe, played by Rachel Cannon, was being too clingy, Charlie begins to get jealous when she starts getting hit on by the attractive handyman. He even goes as far as picking up “trendy” clothes in order to impress her and going to the guy’s house.
Charlie eventually fires the poor guy, but he wins Chloe’s heart. Recently Rachel hasn’t been seen as much, but she had roles in Fresh Off The Boat, The Big Bang Theory, and Mad Men. She’s a self-described entrepreneur and mentor; maybe she doesn’t have a whole lot of time for acting