On September 22, 2003, the first episode of the television sitcom Two and a Half Men premiered starring Charlie Sheen (Charlie Harper), Jon Cryer (Alan Harper), and Angus T. Jones (Jake Harper). The series followed the two and a half men as they Sheen’s character lives a hedonistic life. That lifestyle led to many dates with beautiful women as the series progressed.
After Sheen’s departure from the show, Ashton Kutcher (Walden Schmidt) filled the void playing a recently divorced billionaire. Sheen leaving didn’t stop the flow of estrogen on the show by any means. Since ending in 2015, what are those lovely ladies up to these days?
Kelly Stables – “Melissa”
A woman who had a recurring role on the show was Melissa, played by Kelly Stables. She was Alan Harper’s receptionist, who Charlie tried to get to fall for him. Eventually, she started a relationship with Alan. The relationship ends with Alan breaking up with her over a text.
Today, Stables is a recurring character on the TV show Superstore. She’s landed plenty of roles throughout her acting career as well. Stables has a husband, Kurt Patino and a son as well.
Jennifer Taylor – “Chelsea”
At the beginning of Charlie’s relationship with Jennifer Taylor’s character Chelsea, he strictly saw her as a one-night stand. Over time, that changed as Charlie began to grow feelings for her. As a result, Chelsea had the pleasure of becoming the first woman Charlie ever professed his love to. She ends up leaving him for Alan’s lawyer.
Taylor is now married to Paul Taylor. One of her most recent TV appearances comes from the hit series Shameless. Taylor also has two shows still in post-production.
Courtney Thorne-Smith – “Lyndsey McElroy”
Courtney Thorne-Smith played a slightly masculine character by the name of Lyndsey McElroy. She enjoyed drinking beer and was Alan’s on-and-off romantic partner. She had a serious drinking problem as well. She was very caring, but also a super flirt.
Smith played this role for five years and once it ended, she took a break from the Hollywood lifestyle. She did do a voice a character on the adult cartoon show Robot Chicken before appearing on Fresh Off The Boat.
Emmanuelle Vaugier – “Mia”
Emmanuelle Vaugier’s character Mia was a dance instructor who didn’t give Charlie the time of day. It wasn’t until she found out that Charlie had a nephew who was also interested in dancing that she decided to give Charlie a chance. The two almost get married but that fails when Charlie tells her his brother won’t move out.
The Canadian actress, model, and singer continued to thrive after appearing in this series. She locked down various roles and continues to make her career blossom.
Megan Fox – “Prudence”
During season one, Megan Fox plays a granddaughter who can’t be left alone at home. She ends up getting brought to Charlie’s beach house, where everyone was left stunned by her figure and looks, even Jake!
Fox might be one of the biggest stars on this list. A cameo in this show probably ranks towards the bottom of her career accomplishments. After appearing in huge blockbuster films like Ninja Turtles and Transformers, Fox has been relatively missing from the acting scene.
Up next, someone who appeared to be innocent but deep down had another side…
April Bowlby – “Kandi”
April Bowlby’s character portrayal on the series is that of a young, sweet, and somewhat innocent charmer. Beneath the surface, she enjoyed sleeping with older men, including Charlie. She somehow ends up getting Charlie, Alan, and Alan’s former lawyer too! In the end, she chooses to marry Alan but dumps him after accepting a new job.
These days, you can still catch Bowlby acting. She’s appeared in shows like The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva. The actress also gained some extra notoriety over her relationship with Josh Groban.
Holland Taylor – “Evelyn Harper”
Holland Taylor played Evelyn Harper, Charlie and Alan’s neglectful mother. Many argue that she could easily be the funniest character on the show. Both of her sons tried their hardest to avoid her as much as possible. She would also get with older men for their assets and money.
Taylor still powers through as a recognizable and respected figure in Hollywood. Her talent has allowed her to land jobs in the industry and we love to see her do what she does best.
Marin Hinkle – “Judith Harper-Melnick”
Marin Hinkle played Alan’s first wife, Judith Harper-Melnick. She was also the biological mother of Jake Harper. The relationship she had with Alan was so bad that she admitted to only being happy while pregnant with Jake! The two eventually divorce and she goes on to marry Jake’s pediatrician.
Today, Hinkle is still sharpening her acting chops. You might have noticed her in the CBS series, Madam Secretary. She also was in Homeland and Speechless. Hinkle has a successful marriage with Randall Sommer.
Allison Janney – “Beverly”
Alan met Allison Janney’s character Beverly via a dating site. He really wanted to impress her so he told Beverly that the beach house was all his. Upon feeling bad about her recent divorce issues, he comes clean and reveals that the house is Charlie’s.
How could you not recognize Allison Janney? She’s been in hit movies like Hairspray and Juno. The work she’s done in acting has earned her seven Primetime Emmy Awards, a Golden Globe, and Academy Award, and much more!
Brooke Shields – “Danielle Stewart”
Brooke Shields played a girl with a partying past, but that didn’t stop Charlie from setting her up with Alan. Alan tells Danielle Stewart that he’s going to change for her, something no other guy has told her. After Danielle tells Charlie, “I’ve slept with a lot of guys and even a few women and even with couples,” he all of a sudden wants her and fights Alan, causing her to leave.
Clearly, Shields was already a prominent actress before she appeared on this show. She grabbed her first lead role at the age of 12. You might have caught her on Law & Order: Special Victims Unit.
Jeri Ryan – “Sherri”
Sherri was a type of girl Charlie had never encountered before. She was very skilled at the art of playing hard to get and would constantly lead Charlie to have relations with her. He thought he was the one getting used so he plotted revenge and that’s what led to their downfall.
Jeri Ryan might be best known for her role on Star Trek: Voyager which helped her earn four Saturn Awards. Her latest work is a project called The Relic.
Kimberly Williams-Paisley – “Gretchen Martin”
After one of Alan’s ex-girlfriends begins dating another guy, he decided it would be a bright idea to date that guy’s sister, Gretchen Martin. She becomes a recurring character as she keeps up a relationship with Alan’s alter ego, Jeff Strongman. She eventually calls him out on all his lies and dumps Alan.
You might recognize Kimberly Williams-Paisley from Nashville or According to Jim. She appeared in the later episodes of Two and a Half Men, so after the show, she slowed down acting a bit. She’s probably too busy focused on her marriage with Brad Paisley.
Judy Greer – “Bridget Schmidt”
As Ashton Kutcher’s character gets into the swing of things, the audience soon finds out about his past aka his divorce with Bridget Schmidt. He loved her so much that he was willing to take his life for her. After she discovers that he’s dating someone else, she tries to get him back but it was too late.
Judy Greer is a well-established director, actress, model, and author. Greer has also done great work as a voiceover actress for animated shows like Archer and StoryBots.
Did you know that there was a royal involved in the show??
Sophie Winkleman – “Zoey Hyde-Tottingham-Pierce”
After his divorce, Walden got really cozy and close with Zoey Hyde-Tottingham-Pierce. The pair dated for two seasons and would have gotten engaged had she not rejected Walden’s marriage proposal. Walden later discovers she was dating another man behind his back, and as revenge, he gave her daughter a vicious dog for her birthday.
In real life, Sophie Winkleman is royalty! She’s married to Lord Frederick Windsor, the son of Prince Michael of Kent, Queen Elizabeth II’s first cousin. That’s a long-winded introduction. You can refer to her as Lady Frederick Windsor.
Melanie Lynskey – “Rose”
Melanie Lynskey’s character Rose ended up becoming a regular on the show and one of the audience’s favorites. Charlie thought it was only a one night stand, but it escalated to an obsession. Charlie eventually falls for her and they decide to get married, but Charlie’s character passes away before they make it official.
Hailing from New Zealand, Lynskey plays roles where she is soft-spoken, quirky, and flawed. After this show, she went on to win multiple awards in other acting opportunities.
Ming-Na Wen – “Linda Harris”
Charlie dated pretty much every type of woman. Linda Harris was a judge who he first met after Alan planned a double date. Charlie liked her a lot but she found him to be very repulsive due to his lifestyle.
Ming-Na Wen has a pretty great stat sheet as far as her acting resume goes. Her face might not look familiar, but her voice might be. Wen did the voiceover for Mulan. Her most current role is as Melinda May in Agents of S.H.I.E.L.D.
Heather Locklear – “Laura”
While Alan was going through a rough patch trying to get his divorce settled, something happened. In true Charlie fashion, he messed things up by sleeping with Alan’s attorney, Laura. After Charlie broke his promise being available to her whenever she wanted, she sabotaged Alan’s divorce proceedings.
Even before appearing on the show, Heather Locklear was a well-established name. She’s fought through a publicized divorce and a few health issues. Locklear is ready for more roles, as she’s appeared on Fresh Off the Boat in 2017.
Gail O’Grady – “Mandi”
Remember Kandi from earlier? Well, this is her mother, Mandi, played by the great Gail O’Grady. She first appears when she comes looking for Kandi, but ends up getting intimate with Charlie for the whole day! Kandi and Mandi looked so much alike, the neighbors mistook them for twins.
O’Grady is a producer and an actress. She’s booked tons of lead roles for television movies that ultimately led to her gaining three Primetime Emmy Award nominations. In her personal life, she’s gone through six marriages, all of which have not worked out.
Paula Marshall – “Paula”
Alan meets Paula at a nightclub and the two have chemistry right away. Soon enough, Paula gets comfortable enough to reveal that she used to be a man named Paul. Still, Alan wasn’t bothered. Then, Paula says she wants to be in an open relationship after introducing Alan to her ex-wife Rachel. Rachel and Paula end up giving it another try and leaving Alan in the dust.
Paula Marshall has a lengthy resume of great guest appearances on TV. She’s been in House, Murder in the First, Law and Order and The Mentalist. Marshall has a daughter named Maya as well.
Missi Pyle – “Miss Pasternak”
“I don’t think limits,” a famous quote from the fastest man in the world, Usain Bolt. That must have been Charlie’s inspiration because it didn’t matter who the woman was, he would pursue her. That included Miss Pasternak, Jake’s teacher. Charlie starts dating her and she begins to give Jake good grades without him earning it. Then, Charlie found out she was mentally ill so he dumped her.
In the real world, Missi Pyle is quite accomplished. She’s been in Charlie and the Chocolate Factory, 50 First Dates, and more blockbusters! She keeps busy by working on multiple projects.
Kimberly Quinn – “Donna”
Alan starts dating Donna after a blind date that presumably ended in the bedroom. Unfortunately, the spark fizzled out quickly for Alan who wanted to break up with Donna because he was bored. The only problem was that he was afraid of hurting her feelings.
Donna was played by actress Kimberly Quinn. Outside of Two and a Half Men, Quinn has appeared on many other TV shows such as Grey’s Anatomy and CSI: NY. You might recognize her best as Gretchen on FX’s Terriers or as Tess Masterson on Twisted.
Tammy Lauren – “Shannon”
Alan meets Shannon at Judith and Herb’s wedding in season four. Shannon turns out to be Herb’s ex-fiancée who was in his life before he met Judith. To get back at them, Shannon has a crazy idea to sleep with Alan in the coat closet, despite the fact that Alan wasn’t too keen on the idea.
Shannon was portrayed by Tammy Lauren, who had a prolific television career throughout the ’80s and ’90s before she appeared on Two and a Half Men in 2007. Lauren hasn’t been in much since the show, aside from an episode of Criminal Minds.
Justine Eyre – “Gabrielle”
Gabrielle appears in season five as Gabrielle. She starts out as Charlie’s girlfriend but manages to get whisked away by Alan, who steals Gabrielle as revenge for Charlie previously stealing one of his girlfriends in high school. After Alan feels bad, Charlie encourages him to keep dating her only for Alan to discover her “bedroom style.”
Gabrielle was played by Canadian actress Justine Eyre. Prior to her guest spot on Two and a Half Men, Eyre was known for her role as Karen on Ocean Ave. Most recently, she appeared on the Hallmark Channel’s Winter Castle.
Maggie Lawson – “Mrs. McMartin”
Mrs. McMartin appears on season 12 as a social worker who is sent to Alan’s house as he is interested in adopting. Unsurprisingly, Alan and Mrs. McMartin begin dating only for her to end up heartbroken after she finds out he is still talking to an ex. That revelation leads her straight into the arms of Walden, with whom she starts a relationship.
Mrs. McMartin is played by Maggie Lawson, who is most recognizable for her role as Detective Jules on Psych. In addition to the sequel Psych movie, Lawson can recently be seen as Natalie Flynn on Lethal Weapon.
Denise Richards – “Lisa”
Lisa appears in season one as one of Charlie’s exes who he desperately tries to win back. Charlie lies to her by saying he has turned into a family man but it actually turns out that he has commitment issues. Lisa was played by Denise Richards, who was Charlie Sheen’s wife in real life at the time.
Shortly after her stint on Two and a Half Men, Richards filed for divorce. She and Sheen share two daughters together. These days, you can see Denise Richards on The Real Housewives of Beverly Hills and The Bold and the Beautiful.
Conchata Ferrell – “Berta”
Berta is the housekeeper of Charlie’s (and later Walden’s) home. She is snappy and cynical, but hard-working. She cares for the Harper family despite always making fun of them. She also brings her own family into the Harper home on occasions, getting Alan and Charlie tangled up with her daughters and granddaughters.
Berta is played by Conchata Ferrell. She left Two and a Half Men in 2015 and since then, she’s had roles in Krampus, Grace and Frankie, and The Ranch. Other than that, the 76-year-old keeps a relatively low profile.
Jenny McCarthy – “Courtney Leopold”
“Courtney Leopold” first appears in season five as the daughter of one of Evelyn’s suitors, Teddy. Eventually it’s found out that Courtney was a former Con-Artist, who also goes by the name of Sylvia Fishman. Sylvia returns in season eight and again in season nine, always up to her scheming ways.
She was played by none other than Jenny McCarthy who is recently a judge on The Masked Singer. She also had a recurring role on Return of the Mac and on The Real Housewives of Beverly Hills.
Teri Hatcher – “Liz”
Liz appears in season one of Two and a Half Men as Judith’s “sleaze-ball” sister. At Alan and Judith’s wedding, Liz and Charlie did the deed in the coat closet, which afterward leaves Charlie befuddled when she doesn’t recall the encounter. Liz was played by Teri Hatcher.
Hatcher is best remembered for her role as Lois Lane on Lois & Clark: The New Adventures of Superman and as Susan Mayer on Desperate Housewives. The Golden Globe-winning actress has recently appeared on Supergirl, QI, and All Round to Mrs. Brown’s.
Jaime Pressly – “Tammy”
Tammy appears in season ten as Jake’s 36-year-old girlfriend. Tammy owns Tammy’s Tatties and also has three children, much to Alan’s disapproval. As a mother herself, Tammy understood how Alan felt but what really ended her relationship with Jake was the fact that he slept with her daughter, Ashley.
Tammy was played by Jaime Pressly. Pressly is best remembered for her role as Joy Turner on My Name Is Earl. These days, Pressly is actually a mother of three in real life. Her most recent TV work includes a guest spot on BoJack Horseman and The Guest Book.
Krista Allen – “Olivia Pearson”
Olivia Pearson appears in season one as the daughter of Tommy, one of Evelyn’s boyfriends. Alan, Charlie, and Jake meet Evelyn for dinner, where she plans on introducing them to Tommy. Unfortunately, it’s revealed that Charlie and Olivia previously dated and it obviously didn’t end well since Olivia throws her drink in Charlie’s face.
Olivia is played by Krista Allen, whose most prominent TV work was on Days of Our Lives and Baywatch. Her most recent role was on the TV movie Party Mom but she hasn’t really been seen anywhere since.
Kristin Dattilo – “Cindy”
In season one, we meet Cindy, one of the only women on the show who Charlie doesn’t manage to get in bed with. Cindy was also a friend of Judith’s and as a result, Jake developed a huge crush on her after spotting the butterfly tattoo on her backside.
Cindy was played by actress Kristin Dattilo, who is probably best remembered as Yola Gaylen on The Chris Isaak Show. Dattilo continues to act to this day and has most recently worked on Stuck in the Middle and El Coyote.
Liz Vassey – “Kate McLaughlin”
Kate McLaughlin appears in season one, as divorced mother that Charlie meets at one of Jake’s football games. In the end, she confesses that she hasn’t been with anyone since her husband and that she was overwhelmed with the responsibilities of a single mother. Though Charlie is not so sure about her at that point, they still end up sleeping together.
Kate was played by Liz Vassey, who actually returns in later seasons of Two and a Half Men as a different character. In seasons eight and nine, she plays a dermatologist named Michelle who removes one of Charlie’s moles.
Paget Brewster – “Jamie Eckleberry”
In season one, we learn of an acquaintance from Charlie and Alan’s past named Jamie Eckleberry. They called her “Ugly Eckleberry Hound” when they were kids but as an adult, Jamie lost a lot of weight and became a bombshell. Charlie and Alan both try to hit on her and she is able to get revenge on them both by rejecting them.
Jamie is played by Paget Brewster, who is best known as Special Agent Emily Prentiss on Criminal Minds. These days, you can catch her as the voice of Della Duck on Duck Tales.
Rachel Cannon – “Chloe”
When we meet Chloe, it’s in the season one episode titled “Anteaters. They’re Just Crazy-Lookin.” Chloe is Charlie’s girlfriend who he at first tries to get rid of, but immediately gets jealous once she takes an interest in someone else.
Chloe was played by Rachel Cannon. Cannon has appeared in a number of television shows including Notes from the Underbelly, 2 Broke Girls, and Mad Med. These days, she is best recognized for playing the character of Diedre on Fresh Off the Boat.
Sara Rue – “Naomi”
Naomi appears in two episodes of season four as Berta’s youngest daughter who gets pregnant. After Berta introduces her to Alan and Charlie, Naomi begins to develop for Alan. In fact, the two end up sharing a kiss just before Naomi goes into labor. Later, Naomi gives birth to a daughter named Brittany Pam.
Eventually, she and Alan begin dating and despite trying to hide it from Berta, she is actually quite pleased by the relationship. It doesn’t last long, however, when Naomi ends up with her baby daddy.
Sara Rue Was Recently On A Series Of Unfortunate Events
Naomi was played by Sara Rue. After Rue appeared on Two and a Half Men, she went on to another CBS sitcom, The Big Bang Theory. Outside of other television guest spots and roles in made-for-TV movies, Rue also went on to become the host of Shedding for the Wedding on The CW.
Rue didn’t completely leave acting behind, however. She is best known these days for her role as Carmen Ferrera on Popular and most recently played Olivia Caliban on A Series of Unfortunate Events.
Stephany Jacobsen – “Penelope”
Penelope appears later on in the series. In the season nine episode, “People Who Love Peepholes, we meet Penelope, a woman who appears at Charlie’s house to see him. Unfortunately, she did not get the news about Charlie’s death and doesn’t even know that his house was now owned by Walden.
Though Penelope is shocked to hear of Charlie’s death, she immediately forgets about him when she sees Walden. Later in the episode, Alan has to pretend to be Penelope’s girlfriend when Walden’s wife shows up at the house. Read on to see who the beautiful actress behind Penelope is.
Stephany Jacobsen Maintains A Low Profile
Penelope was played by Stephany Jacobsen, who is pretty hard to track down online. What we do know is the fact that she did continue to act after appearing on Two and a Half Men. Prior to going on that show, she was on Melrose Place as Lauren Yung.
In more recent years, you might have noticed Jacobsen as Niko Takeda on Revenge. You may have also seen her play Eva Benton on Star-Crossed or on NCIS and Hawaii Five-0. At the very least, she went from playing a one-off character to having recurring roles.
Miley Cyrus – “Missi”
Outside of Alan’s and Charlie’s plethora of flings and girlfriends, what fans really liked to see was any of Jake’s love interests. After all, the kid has been on the show since he was, well, a kid and it’s always interesting to see how they grow up. One of his first girlfriends was Missi, though we don’t meet this character until season ten.
Missi first appears in the episode “You Do Know What The Lollipop Is For,” when Jake comes home from the Army. After Jake goes AWOL, Missi feels uncomfortable about his feelings for her and she convinces him to return to the Army.
Miley Cyrus Is Making A Comeback
Missi was played by none other than Miley Cyrus. Cyrus appeared on her show during her Bangerz era, in which she was overtly provocative much to the shock of the public. Of course, we all knew that this was just a way for her to shed her Disney Channel image from playing Hannah Montana all those years.
After a brief period of laying low from her wild days, Cyrus’s career was on a steady rise. She appeared as a judge on The Voice and released new music that tapped into her country roots. In 2018, she finally married Liam Hemsworth.