Two and a Half Men’s Charlie, Alan, and Jake had one of the most exciting bachelor lifestyles together. Stretching over the course of 13 years and 12 seasons, the show saw many adventures and many talented actresses, some of whom were relatively unknown at the time when they appeared on the show. But these women who helped make the series what it is have used their talent in many other remarkable ways, too.
1. Kimberly Quinn as Donna
After meeting Alan on a blind date in the season five episode, “Dum Diddy Dum Diddy Doo,” the two have a brief relationship before Alan, bored with the romance, abruptly breaks it off. Donna is played by Kimberly Quinn, also known for her roles in the FX series Terriers and ABC Family show, Twisted.
While Quinn has had numerous roles in various television shows since 1995, it appears as though the former Two and a Half Men guest star has decided to transition towards film acting. Her most recent short film, The Take Off, was released in 2018 and two of her upcoming films Follow Me, and The Starling (which she also gets a producer credit on) are due to be released in the near future.
2. Kelly Stables as Melissa
Melissa is Alan’s former receptionist and later girlfriend, whose tumultuous relationship with the Harper brothers takes place throughout seasons six, seven, and eight. The actress who played Melissa, Kelly Stables, is no stranger to television acting, and is known for her roles as Eden Konkler on The Exes and Kelly on Superstore.
Stables’ career isn’t just relegated to the small screen though. The St. Louis, MO native has been acting on the silver screen since 2002 after she landed her first role in the Spider-Man film starring Tobey Maguire. Stables’ most recent film role was in 2014’s Horrible Bosses 2, however, as it looks like the actress chose to focus on television and voice acting.
3. April Bowlby as Kandi
Actress April Bowlby plays Kandi, Alan’s sweet and innocent second ex-wife. While the character isn’t exactly portrayed as the brightest bulb in the drawer, she is able to maintain a positive relationship with Alan after their divorce, unlike his drama-filled relationship with ex-wife number one, Judith.
Previously a model, the Vallejo, CA native secured the role of Kandi within months after first appearing in audition rooms in Hollywood. Since then, Bowlby has become very familiar with the glow of the limelight and one of her her latest projects, the 2019 television show Doom Patrol, features her starring as Rita Farr, aka Elasti-Girl, in the DC universe.
4. Megan Fox as Prudence
Before starring next to Shia LaBeouf in the blockbuster hit Transformers, Megan Fox played Berta’s flirtatious granddaughter in one episode of the first season of Two and a Half Men. In that episode, Berta, very protective of her adventurous granddaughter, forces her to follow her around everywhere and becomes progressively more annoyed as the guys are unable to leave her side.
Fox’s career didn’t take off until after her role in 2007’s Transformers and its sequel Transformers: Revenge of the Fallen. Recently, in 2014 and 2016, Fox played the role of April O’Neil, the Ninja Turtles’ first human ally in the Teenage Mutant Ninja Turtles movies, and has roles in no less than three upcoming films whose release dates fans are excitedly anticipating.
5. Courtney Thorne-Smith as Lyndsey McElroy
Alan first meets Lyndsey McElroy after her son, Eldridge, is discovered to have convinced Jake to try and steal beer from Charlie. Whereas Alan’s intent was to tell on Eldridge, he quickly forgets about the beer incident after becoming enamored by Lyndsey and the two begin dating. She then becomes a major character in the series from season seven onward.
Film Industry Digest lists the actress behind Lyndsey, Courtney Thorne-Smith, as one of those Hollywood gems who “hasn’t gotten the type of credit that she deserves.” Her knack for working on successful shows non-stop from 1992 to 2015 hasn’t gone unnoticed by everyone though, and today Thorne-Smith has chosen to stay with television, appearing in back to back television roles for the past 3 years.
6. Marin Hinkle as Judith Harper-Melnick
One of the more complicated relationships of the show, Marin Hinkle plays Alan’s first ex-wife and Jake’s biological mother, Judith Harper-Melnick. While their behavior towards each other is often cold, the series hints that Alan may still harbor suppressed feelings for his ex, particularly when he begins having dreams of her.
After the show ended in 2015, Hinkle went on to make quite a name for herself, and earned critical acclaim for her role as Rose Weissman on the Amazon Prime Video series, The Marvelous Mrs. Maisel. The show itself has been the recipient of numerous accolades, with Hinkle receiving an Emmy nomination for Outstanding Supporting Actress in 2019 for her work on the show.
7. Jennifer Taylor as Chelsea Melini
Chelsea Melina wasn’t just Charlie Harper’s ex-fiancé, she was one of the few women on the series who he truly loved. Chelsea (played by Jennifer Taylor) and Charlie’s relationship took place in season six and throughout most of season seven. Ultimately, her story line ended after she broke off the engagement with Charlie – and starts dating Alan’s attorney instead.
Before getting the role on Two and a Half Men, actress Jennifer Taylor was planning on quitting acting and moving back to Florida to become a teacher instead, but the role ended up changing those plans. She is still living in Los Angeles with her husband and two children and most recently appeared in the 2018 film, God’s Not Dеаԁ: A Light in Darkness.
8. Emmanuelle Vaugier as Mia
With multiple acting credits in television, film, and video games to her name, Emmanuelle Vaugier’s almost 25 year career includes her role in 10 episodes on Two and a Half Men. There Vaugier played Mia, Charlie’s ex-fiancé who tries to pressure him into living a healthier lifestyle in season three, causing the relationship to inevitably fall apart.
More recently, Vaugier took a role in the TV movie, Killer Ending, which premiered in 2018. But she hasn’t always been a television star. Vaugier’s noteworthy film accolades include appearances in the popular horror franchise Saw. Additionally, the Canadian-born actress starred alongside legendary actors Michael Caine and Robert Duvall in 2003’s Secondhand Lions.
9. Allison Janney as Beverly
Academy Award winning actress, Allison Janney made a brief, one episode appearance on Two and a Half Men’s season four as one of Alan’s love interests. On that one fateful episode, Alan invites Beverly over to Charlie’s place, but instead of being truthful, he lies tells her it’s his in order to impress her.
Who wouldn’t be tempted to lie in order to impress the one and only Allison Janney? Not only has she won an Oscar, but this incredibly accomplished actress is also the recipient of seven Emmy Awards, a BAFTA, and a Golden Globe. Most recently, Janney had roles in three 2019 films, Bad Education and The Addams Family, and Bombshell alongside Margot Robbie and Charlize Theron.
NEXT: She might not have been recognizable then, but this actress’ career took off after this spotlight appearance.
10. Jeri Ryan as Sherri
Considered by Charlie to be the female version of himself, Sherri is a formidable woman who is able to manipulate both Charlie and Alan by skillfully playing hard to get. She is only featured in three episodes, two in season two and one in season nine.
It might be a surprising realization, but the actress behind Sherri, Jeri Ryan, is actually less known for roles in comedy series but rather for playing the Borg drone, Seven of Nine, in the acclaimed Star Trek: Voyager. Ryan’s performance was so good that she was nominated four times for a Saturn Award (winning once) and will reprise her role in the upcoming CBS series, Star Trek: Picard.
11. Brooke Shields as Danielle Stewart
Played by Brooke Shields, Danielle Stewart appears in season four’s episode, “That’s Summer Sausage, Not Salami.” Danielle is Charlie and Alan’s wealthy next door neighbor. Charlie attempts to set Alan up on a date with her, and is forced to act as his brother’s dating coach after the latter fails to woo her independently.
Actress Brooke Shields is known primarily for her work in television and has been in starring roles since she was a kid. At age 18, she was forced by her parents to put her acting career on hold in order to attend the prestigious Princeton University where she graduated with a degree in Romantic Languages. More recently, Shields has had appearances in a number of high-profile television shows, including Law and Order: SVU and Jane the Virgin.
12. Kimberly Williams-Paisley as Gretchen Martin
Appearing as a recurring character throughout season eleven, Gretchen Martin used to date Alan thinking he was “Jeff Strongman,” his alter ego. In reality, the talented and versatile Kimberly Williams-Paisley’s three decades in Hollywood include multiple credits as an actress, directer, producer and writer.
Williams-Paisley has been acting since 1990 and hasn’t stopped since. Her most recent work includes a role in the 2019 television movie, Witness to Murder. This busy actress is also set to star in an unannounced role in the upcoming drama film, The Violent Heart.
13. Judy Greer as Bridget Schmidt
In season nine of Two and a Half Men, Charlie Sheen’s character, Charlie Harper, is replaced by Ashton Kutcher playing Walden Schmidt. Walden is accompanied by ex-wife Bridget Schmidt who, while appearing to be sweet and innocent, soon shows a more devilish side and quickly becomes the antagonist of the season.
When it comes to actress Judy Greer, it seems as though this Hollywood star is never far from a major film or television set. In 2019, Greer had starring and supporting roles in more than a few films and TV shows, including the animated series Archer, Playing with Fire, and Kidding alongside Jim Carrey.
14. Sophie Winkleman as Zoey Hyde-Tottingham-Pierce
Much like her real-life counterpart Sophie Winkleman, the Two and a Half Men character with the mouthful of a name, Zoey Hyde-Tottingham-Pierce was born in the United Kingdom. Unlike the actress, Zoey, Walden’s ex-girlfriend, is an attorney at law. She was his first love interest since his split from his ex-fiancé, Bridget Schmidt.
Born in Primrose Hill, London, actress Sophie Winkleman is also known as Lady Frederick Windsor, as she is married to Lord Frederick Windsor, the Queen’s second cousin. Being part of the royal family hasn’t stopped Winkleman from acting however, and in 2019 she appeared in two British television series, Endeavour and Sanditon.
NEXT: Most people aren’t aware that this famous star once had an appearance on Two and a Half Men.
15. Melanie Lynskey as Rose
One of the main characters of the show, Rose becomes obsessed with Charlie after a brief romantic encounter and eventually advances to moving in next door. After that, she starts to stalk Charlie at every opportunity. After eight years, Rose’s persistence pays off and she runs off to Paris with Charlie. Post his off-screen death, Rose sets her sights on a new man – Walden Schmidt.
The Two in a Half Men star is played by award winning actress, Melanie Lynskey who is, a prominent figure in the independent film industry. Recently, the New Zealand-born actress had a starring role as Molly Strand on the 2018 Hulu series, Castle Rock and is currently filming an upcoming 2020 series, Mrs. America.
16. Ming-Na Wen as Linda Harris
Throughout season five, Linda Harris, played by Ming-Na Wen, is a judge who becomes enamored with Charlie and decides to give him a second chance. She later becomes Charlie’s girlfriend, but the relationship is short lived, and Linda leaves Charlie after seeing a compromising photo of him in the newspaper.
Actress Ming-Na Wen is best known for her work in television, but animated film fans are most likely to know her as the voice behind Disney favorite Mulan. More recently, Wen seems to have had a busy 2019, having acting credits in multiple TV series and one short film. Fans of the actress are gearing up to watch her in the upcoming Disney+ series, The Mandalorian, which takes place in the Star Wars universe.
17. Heather Locklear as Laura
Appearing in the 21st episode of season one, Laura Lang is Alan’s expensive, Beverly Hills based divorce attorney, who after a brief and sudden romantic relationship with Charlie, takes revenge by trying to mess up Alan’s divorce proceedings.
Before her guest appearance on Two and a Half Men, Heather Locklear was already an award winning actress, having won four Golden Globes consecutively for her work on Melrose Place (1993-1999). After a brief break from television and cinema, Locklear returned to focus on acting, with her most recent role being a recurring guest-star role on Tyler Perry’s TLC drama, Too Close to Home.
18. Gail O’Grady as Mandi
Gail O’Grady played the very brief role of Mandi, Kandi’s mother. Mandi has a two episode-long passionate relationship with Charlie during season three of Two and a Half Men, before their it was discovered by Alan, his first ex-wife Judith, and Mandi herself.
Acting since 1986, Gail O’Grady has landed a number of lead roles on television series and TV movies. Her work has even earned her three Primetime Emmy Award nominations. O’Grady doesn’t seem as though she’s slowing down any time soon , however, and she was recently featured on TV movie, Identity of a Cheerleader, and also as a recurring character on Criminal Minds.
19. Miley Cyrus as Missi
Described as quirky and odd, albeit well-meaning and kind, Missi is Jake’s girlfriend who he eventually goes AWOL from the army for. After confessing his feelings for her, Missi, feeling uncomfortable, tells Jake that she isn’t ready for a real relationship and convinces him to go back to the army.
At only 26 years old, Miley Cyrus has already released her seventh studio album, “She is Miley Cyrus,” which debuted as three, six-song EPs throughout 2019. Cyrus also had a leading role on an episode of Netflix’s popular science fiction series, Black Mirror. More recently, Cyrus teamed up with fellow songstresses Ariana Grande and Lana Del Rey for the theme song of the 2019 film Charlie’s Angels.
20. Denise Richards as Lisa
In spite of being obviously in love with her, Charlie is unable to maintain a relationship with Lisa since she wants a committed relationship, something that Charlie is unable to do. Featured in just two episodes in seasons one and two, Charlie makes a few attempts at showing her that he’s changed, which she sees through immediately.
Not only did Denise Richards’ Lisa date Charlie Sheen’s Charlie, but in real life the two actors were an actual couple for several years, and have two daughters together. When she’s not busy being a mom of three, Richards maintains a bustling acting career, appearing in hits like The Bold and the Beautiful, The Secret Lives of Cheerleaders, and Jane the Virgin.
21. Missi Pyle as Miss Pasternak
One of Charlie’s many girlfriends, Missi Pyle’s character is Miss Pasternak, Jake’s fifth grade teacher who suspends him after he gives her a rude gesture. Two and a Half Men was hardly Missi Pyle’s first guest appearance on a popular series however, having also worked on popular shows like Heroes, Frasier, and Friends.
Considered to be a very versatile actress, Pyle has taken roles in everything from comedies, to horror flicks, and even award-winning dramas. Her 2019 work involved appearances in the drama biopic Walk. Ride. Rodeo, along with horror film, Ma. This was in addition to her television work with Drunk History and Bob Hearts Abishola.
22. Krista Allen as Olivia Pearson
Olivia Pearson has a very brief appearance on Two and a Half Men. While it is revealed that she and Charlie had dated at one point, the relationship is never shown. Rather, after meeting at a party, the two engage in a very serious conversation which quickly breaks down and results in Olivia throwing a drink in Charlie’s face before storming off.
Model/actress Krista Allen is known both for her film appearances as well as her work in television. She appeared on the television series Days of Our Lives, as well as the popular show Baywatch along with her roles in the films The Final Destination and Anger Management. Recently, her career has involved more TV movies releasing Party Mom in 2018 and I Almost Married A Serial Killer in 2019.
23. Jaime Pressly as Tammy
Only appearing in two episodes in season ten, Tammy nonetheless shocked fans (not to mention Alan and Walder) after she began dating Alan’s son Jake, despite being nearly double his age. The two inevitably fell out and Tammy found solace with Schmidt, who is closer to her in age and in maturity.
Born in Kinston, North Carolina, Jaime Pressly is known for both film and TV work but found her greatest career successes working in television, namely the NBC sitcom My Name is Earl. Her work on the show earned her an Emmy Award as well as numerous other prestigious nominations.
24. Teri Hatcher as Liz
Appearing in one episode aptly named, “I Remember The Coatroom, I Just Don’t Remember You,” Liz pretends not to remember Charlie after a brief encounter. This seriously bothers him since Charlie is used to having the upper hand in relationships with women and not the other way around.
Liz is played by Teri Hatcher, who is most recognizable for her portrayal of Lois Lane on the series Lois & Clark: The New Adventures of Superman, as well as Susan on Desperate Housewives. Acting isn’t Teri Hatcher’s only skill, though – she’s also a talented cook, and has even won an episode in season 17 of the popular Food Network cooking competition, Chopped.
25. Holland Taylor as Evelyn Harper
Appearing in 98 episodes, Holland Taylor played Evelyn Harper, the self-absorbed and conceited mother of Charlie and Alan. Two and a Half Men got lucky hiring Taylor, a Primetime Emmy Award winning actress for her work playing Judge Roberta Kittleson in The Practice. The famed actress has also lit up the theater stage with her work, and was nominated for a Tony in 2013.
Nowadays the Two and a Half Men star is still very active in film and television. The actress is set to appear in two upcoming films in 2020, including the classic Bill & Ted sequel, Bill & Ted Face the Music. Together with partner, award winning actress Sarah Paulson, Holland Taylor is a true powerhouse.
