The Countless Women From Two And A Half Men – Where Are They Today?

We all loved watching the hit show “Two and a Half Men”, taking a look into Charlie Harper’s crazy life with his brother, Alan, and his nephew, Jake. We laughed at the stalker, Rose, and cherished the fights between Alan and his ex-wife Judith. We had countless laughs watching Charlie and Alan going through the emotional turmoil with their mother, Evelyn. There was one thing common in all the episodes and that was the countless women with whom Charlie had relations. While there were some memorable ones like Chelsea, Courtney, and Mia, there were also those who we tend to forget at times. All these women were crucial in proving how carefree Charlie was in his life – but where are they today?

Jeri Ryan as Sherri

Although Charlie had dated numerous different kinds of women, Jeri Ryan’s Sherri was the type of girl he had never encountered before. The German-born American actress is best known for her role in Star Trek: Voyager for which she garnered four Saturn Award nominations. She’s also known for performances in the television shows Dark Skies, Boston Public, and Shark.

Gail O’Grady as Mandi

Although she was the mother of Kandi and Andy’s ex-wife, this did not stop her from having a sexual encounter with Charlie. Aside from taking numerous lead roles in television, Gail O’ Grady has also had the pleasure of going through six marriages. However, she still believes in love as she is currently dating Chris Beyers.

Emmanuelle Vaugier as Mia

Emmanuelle Vaugier played Mia, a dance teacher who supposedly had no interest in Charlie. As a Canadian actress, singer, and model, Emmanuelle Vaugier went on to nail several acting jobs like Lost Girl and Mistresses. Her recent appearance was in a television movie entitled Killer Ending and has future projects like Masks Don’t Lie, My Mother’s Stalker, and Don’t Look There, lined up.

Jennifer Taylor as Chelsea Melini

Jennifer Taylor was given the honor to be the first girl Charlie ever confessed his love to, but outside the show, she married Paul Taylor. This American actress continued with her acting career after her appearance on the show. Besides appearing in various television shows and films such as Shameless, she also has two upcoming shows in post-production entitled Unfaithful and A Deadly Romance.

Denise Richards as Lisa

Lisa, played by Denise Richards, was one of Charlie’s love interests from season one. Surprisingly, Charlie Sheen and Denise Richards were married for four years and had two daughters named Lola and Sam. Despite their marriage ending, her career, on the other hand, didn’t. After she starred in the E! reality show, Denise Richards: It’s Complicated, Richards jumped from the comedy sitcom Blue Mountain State to her current role in The Real Housewives of Beverly Hills.

Missi Pyle as Miss Pasternak

Miss Pasternak was Jake’s fifth-grade teacher, and surprisingly, this didn’t stop the two from dating, giving Jake a boost in his studies. A long list of her movies includes Big Fish, The Artist, 50 First Dates, Gone Girl, and Charlie and the Chocolate Factory. Missi Pyle has surely maintained a successful career and doesn’t show any signs of slowing down.

Kelly Stables as Melissa

Kelly Stables had a recurring character in the show as Alan Harper’s receptionist. After her appearance in the show, Stables landed numerous acting roles throughout her career, such as a role in the hit comedy movie, Horrible Bosses 2. Today, she is currently working as another recurring character on the television show, Superstore.

Courtney Thorne-Smith as Lyndsey McElroy

Courtney Thorne-Smith played the masculine girl who enjoyed drinking beer with her on-and-off lover, Alan. After five years of playing the role and voicing various characters in films, Courtney Thorne-Smith decided to take a break from Hollywood. Today, she spends most of her time with her husband Roger Fishman, and their son, Jacob.

Megan Fox as Prudence

In a first season episode, Megan Fox played Berta’s granddaughter, Prudence. Fox is now one of the most successful women on the list, considering all her blockbuster movie roles after the show – Hope & Faith, Transformers, and Teenage Mutant Ninja Turtles. In recent years, however, Megan has chosen to slow down on her television and film appearances.

April Bowlby as Kandi

In the show, April Bowlby played Kandi, a sweet and somewhat innocent 22-year-old who slept with older men like Charlie. Like many women on the list, Bowlby is still actively acting. She’s appeared on many television shows such as CSI, The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva.

Marin Hinkle as Judith Harper-Melnick

Marin Hinkle played Judith Harper-Melnick, Alan’s first wife, and the biological mother of Jake Harper and Milly Melnick. Today, Marin Hinkle is 51 years old and continues to develop her acting career. Besides appearing in the dramatic series Madam Secretary, Hinkle also played a few roles in Speechless and Homeland.

Allison Janney as Beverly

Allison Janney played the role of Beverly, a woman that Alan met through an online dating site. Most of you may have recognized her from her roles in Hairspray, Juno, and The Girl on the Train. Her work on the big screen and stage has brought her numerous accolades such as seven Primetime Emmy Awards, an Academy Award, a BAFTA Award, and a Golden Globe Award.

Brooke Shields as Danielle Stewart

Danielle Stewart, played by Brooke Shields, was the girl with a partying past who Charlie tried to set up with Alan. Shields was an already notable actress before she appeared on the show. Receiving her first role at the young age of 12, Shields continued to book significant roles on television and in films like The Blue Lagoon, Endless Love, and Law & Order: Special Victims Unit.

Kimberly Williams-Paisley as Gretchen Martin

After Alan’s ex-girlfriend eloped with another guy named Larry, Alan went on to date his sister, Gretchen. Although she seemed to slow down after acting in the show, she still made guest appearances on George Lopez, Tales From The Crypt, and Less Than Perfect. Today she is focusing more on her happy marriage with Brad Paisley.

Judy Greer as Bridget Schmidt

Judy Greer played the ex-wife of Walden (Ashton Kutcher). You have probably seen her in numerous shows and films over the years. Aside from voiceovers for StoryBots and Archer, her most recent appearances were in Ant-Man and the Wasp, Halloween, and Driven.

Sophie Winkleman as Zoey Hyde-Tottingham-Pierce

Zoey played a gorgeous British girlfriend of Walden for two seasons, but sadly, Walden discovered that she was dating another man behind his back. Today, Sophie Winkleman has gone to pursue royalty and married Lord Frederick Windsor, son of Prince Michael of Kent. However, royalty didn’t seem to hinder this actress from continuing her acting career.

Ming-Na Wen as Linda Harris

Although they met through a double date with his brother, Charlie went on to date a judge for a brief period. Besides being the voice of Mulan, Ming-Na Wen starred in the ABC action drama series, Agents of S.H.I.E.L.D and as Dr. Jing-Mei Chen in ER. Aside from the television shows, she was also cast for films like Street Fighter, The Joy Luck Club, and Final Fantasy: The Spirits Within.

Heather Locklear as Laura

During Alan and Judy’s divorce settlement, Charlie decided to mess things up by sleeping with their lawyer, Laura. Despite having a very public divorce and several health issues, Heather Locklear has gotten back on the saddle of acting. Recently she has appeared in Franklin & Bash and Tyler Perry’s Too Close To Home.

Paula Marshall as Paula

Paula, formerly known as Paul, was one of their few partners of Alan, and sadly, she wanted an open relationship after seeing Alan’s ex-wife. As of today, Paula still thrives in her acting career, appearing in shows like House, Law and Order, Murder in the First, The Mentalist, Switched at Birth, and a film titled We Love You, Sally Carmichael! She also married titanic star Danny Nucci.

Kimberly Quinn as Donna

Despite meeting on a blind date and hitting it off pretty well, Alan decided to dump her because he was bored. Quinn indeed proved that she was more than just an actress and can do quite more behind the camera. Alongside her writer-director husband, she also engages in acting, writing, producing, and directing.

Justine Eyre as Gabrielle

Although she was Charlie’s girlfriend at first, Alan was seeking revenge and decided to steal her from him. After the show, Eyre was still able to land a few roles in television shows like Mad Men, The Secret Life of the American Teenager, and CSI: Miami. In recent years, her career has somewhat stagnated.

Maggie Lawson as Ms. McMartin

In the show, Ms. McMartin, played by Maggie Lawson, was a social worker assigned to Walden and Alen after they decided to adopt a child. Even after the show, Maggie Lawson maintained a flourishing career with roles in Angel From Hell, The Great Indoors, Psych, and sitcoms like Inside Schwartz, Crumbs, and It’s All Relative. She also tried her hand in the film industry, appearing in the movie version of Psych.

Melanie Lynskey as Rose

Despite being a one-night stand with Charlie, her role seemed to blossom into one of the main characters and a crowd favorite. After the show, she went on to win various awards like a New Zealand Film Award, a Hollywood Film Award, and a Sundance Special Jury Award. Her most recent endeavors were in films titled I Don’t Feel At Home In This World Anymore, Happy Christmas, The Intervention, and Sadie.

Holland Taylor as Evelyn Harper

Because of Taylor’s role as the neglectful mother of Alan and Charlie, Evelyn Harper gave us one of the show’s funniest characters. Today, Taylor is 75 years old, and despite her age, she is still working regularly. Her performances can be seen as Judge Roberta Kittleson in The Practice and Ruth Dunbar in Bosom Buddies.

Jenny McCarthy as Courtney Leopold

Jenny McCarthy was one of the 90s biggest sex symbols, acting in several films and television shows, as well as appearing in Playboy. On Two and a Half Men, the blonde bombshell portrayed Courtney Leopold AKA Sylvia, a woman who dates Charlie several times. In the years since, McCarthy has co-hosted The View, marred Donnie Wahlberg, and… ugh… become a noted Anti-Vaxxer.

Tammy Lauren as Shannon

Tammy Lauren portrayed Shannon, Herb’s ex-fiancé who met Alan at Herb and Alan’s ex-wife Judith’s wedding. The two jilted exes decided to fake a relationship to make their respective former significant others jealous. She’s also acted in the soap opera The Young and the Restless and appeared on an episode of Criminal Minds.

Krista Allen as Olivia Pearson

Well-known Days of Our Lives actress Krista Allen portrayed Olivia Pearson, an ex-girlfriend of Charlie whose father dates Charlie and Alan’s mother. Allen has continued acting since, appearing in numerous films and television shows.

Teri Hatcher as Liz

Whether young her as Lois Lane, Jerry Seinfeld’s “real and spectacular” girlfriend, Teri Hatcher was one of the most recognizable television actresses of the 1990s. In Two and a Half Men, Hatcher portrayed Liz, Alan’s ex-wife’s sister who hooks up with Charlie. Shortly after appearing on the series, Hatcher scored the biggest role of her career on Desperate Housewives. Following that show’s successful run, Hatcher has continued to appear on television and in film.

Kristin Dattilo as Cindy

Kristin Dattilo’s Cindy had the distinction of being one of the few female characters on the series not to become romantically involved with Charlie, much to his chagrin. Datillo, who costarred on The Chris Isaak Show before her Two and a Half Men fame, has continued to appear in guest roles on television since.