What Ever Happened To The Women Behind Two And A Half Men?

Two and a Half Men solidified itself in comedy and television history. The production of the show was never smooth sailing. During its eighth season, Charlie Sheen, one of the show’s titular leading men, Charlie, took a break to deal with his drug addiction issues. Following this and tension between Sheen and the show’s creators, his character was killed off to make way for his replacement, Walden, played by Ashley Kutcher.

Best known for her time on Star Trek: Voyageras the catsuit-clad Seven of Nine, this German-native actress appeared on the show as Sherri, first as Charlie’s girlfriend, then, strangely enough, as the girlfriend of his brother, Alan.

Mandi, played by the gorgeous redhead Gail O’ Grady, was Andy’s ex-wife and the mother of Kandi, but that didn’t stop this fiery lady from intimately getting involved in Charlie’s love life. After she went on to have a prolific career on TV.

Mia, played by the Canadian actress Emmanuelle Vaugier, first appeared on the show as Jake’s dance instructor after he became interested in learning to dance.

On the show, Chelsea, played by Jeffifer Taylor, played Charlie’s first love—or at least the first person we saw him confess his love to on the show. Before playing Chelsea, she appeared on the show three other times in minor roles. She had a prolific career before and after Two and a Half Men.

Denise Richards had made a name for herself before Two and a Half Men. But on the show, she portrayed Charlie’s girlfriend from seasons one and two. During her work on the show, she was actually married to Charlie in real life. They even had two daughters together.

Isn’t it strange how most of the characters on Two and a Half Men have names that are quite similar to their real-life counterparts? Missi Pyle played Miss Pasternak, Jake’s extremely emotionally volatile fifth-grade teacher and, later on, Charlie’s girlfriend.

First appearing in season six as Alan’s receptionist, she dated both Charlie and Alan, eventually breaking it off with Alan before the end of the season after sleeping with her mother. After leaving Two and a Half Men she took minor roles in several TV shows.

Courtney Throne-Smith was one of the writers for the show and also was one of the boys—she liked to drink beer and get rowdy with the cast. She was nominated several times for a Screen Actor’s Guild for her work on Ally McBeal, winning with the rest of the cast in 1999.

Even true fans might have forgotten about this character as her appearance was so brief. Berta, Charlie’s housekeeper, had a daughter named Prudence, played by Megan Fox. Since her one-time appearance, Megan went on to become a household name, although her career has slowed down lately, perhaps due to her engagement with Machine Gun Kelly.

April Bowlby played Mandi’s- older- men-enjoying, 22-year-old daughter, Kandi. April has had a long list of roles on television, especially in sitcoms. Two and a Half Men was one of her earliest significant roles.

Evelyn was one of the funny characters on the show. Evelyn Harper, played by Holland Taylor, played Alan and Charlie’s mother. It was obvious on the show that she had neglected them both, and as a result, they both developed abhorrent behavior—especially when it came to relating with women. 

Judith, played by Marin Hinkle, was an important character in Two and a Half Men. She was Alan’s ex-wife and Jake’s biological mother. In the show, Judith lied about being gay as an excuse to end the marriage. It later turned out that she had been lying and that she wasn’t actually interested in women.

Back when Two and a Half Men aired, online dating was a niche idea. In the show, Alan met Beverly, played by Allison Janny, on a dating network. Alan tried to convince her that he was wealthier than he was by telling her that he owned the beach house instead of Charlie.

Brook Shields was an already-established actress and model before appearing on Two and a Half Men. She’s had many roles in different projects, including Law & Order: Special Victims Unit, The Blue Lagoon, and Endless Love.

Gretchen, played by Kimberly Williams-Paisley, appears late in the show. She was one of Alan’s love interests. Alan, seemingly unable to present himself honestly to her, deceives her and plays his alter ego, Jeff Strongman, to win her affection. He was unsuccessful. 

In season nine, after we are introduced to Walden, played by Ashton Kutcher, we are also introduced to his ex-wife, Bridget, played by the ever-hilarious Judy Greer. Walden was devastated by their breakup and even considered ending his own life.

Sophie Winkleman played Waldon’s rebound British girlfriend and would-be-fiance. After Walden finds out that she had been seeing another man, he gives her daughter a vicious dog as a gift as revenge. That might sound like something a psychopath would do, but the laugh track assures us that it’s comedy gold.

As long as the stalker is a beautiful woman, there’s nothing wrong with that type of behavior—in fact, it might even lead to a lasting relationship—at least according to Two and a Half Men’s Rose, played by Melanie Lynskey. Unfortunately, this stalker-turned-bride was killed off before she had the chance to alter the status quo.

Charlie met Judge Linda Harris, played by Ming-Na Wen, on a double date with his brother Alan. While Charlie was fond of her, she found his behavior intolerable. Hilariously, Charlie ended up drunk driving (in the show) and ended up in front of her in court. Wowza! 

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!

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.

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!

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. 

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.

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.

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 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.

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.

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.

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.

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?

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.

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’s housekeeper, Berta, has a daughter named Naomi, played by Sara Rue. She moves in after becoming financially and emotionally dependent on her mom after also losing her job. Of course, this is Two and a Half Men, so she develops feelings for Alan, and the two start dating (of course). Strangely, her mother approves of this relationship.

Miley Cyrus showed up in Two and a Half Men in an era where Jake had grown up, and Charlie had died. Missi is a talkative young woman with a kind heart. She comforted Jake and hung out with him when he had trouble at the army base. Upon realizing that he had gone AWOL, however, she let him go.

Everyone knows Mila Kunis! But did you know that she’s actually married to Ashton Kutcher, Walder, in real life? She played a hippie hiker in one of the later seasons of the show, in which she stopped Walder from proposing to his girlfriend after she returned from vacation.

Shannon, played by Tammy Lauren, has a complicated backstory. Needless to say, Alan hit on her, and of course, she was very attracted to him. Of course, the relationship seemed to be moving too quickly for him, and so he broke it off with her.

Well, fancy that. After all that slobbish womanizing, Charlie finds himself spending eternity in the body of a woman in the afterlife. Alan saw this visage when he came close to death. Charlie appeared to him as Kathy Bates to offer a word of advice, cigar and all.

Feeling a little bit like a lecherous old man, Alan decides to go for someone his senior. He found Nora (Cloris Leachman), a wealthy elderly lady with a robust appetite for younger men. Unfortunately, she died on top of Alan in his bed. We wonder if this was the first time Alan saw death.