Where Are the Women from Two and a Half Men Today?

Two and a Half Men is an American television sitcom that originally aired on CBS for 12 seasons from 22 September 2003 to 19 February 2015. On the eighth season, CBS felt that a break was needed. After the break, the series continued with the addition of a new main character played by well-known Hollywood superstar, Ashton Kutcher.

It is somewhat ironic that a series titled “Two and a Half Men” featured so many female characters, but the show would undoubtedly be less amusing and entertaining without them. This entertainment encouraged huge audiences to tune in week after week to discover which famous female actress Charlie would turn his attention to next. We’ve compiled a “then and now” list of some of the most iconic women that made appearances, detailing their roles in the show and their endeavors since.

Gail O’Grady as Mandi

Mandi is Kandi’s mother and Andy’s ex-wife. She is first seen looking for Kandi in Charlie’s House, eventually ending up having sex with Charlie the entire day. Kandi and Mandi looked so alike that strangers mistook them for sisters.

Gail O’Grady as Mandi

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Although she is both an actress and producer, Gail Ann O’Grady is best known for her appearances on television. To date, she has been nominated for a Primetime Emmy Award three times. Her personal life, however, is not so clear-cut, as she has had six marriages.

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Denise Richards as Lisa

Played by Denise Richards, Lisa was one of Charlie’s love interests in season one. She and Charlie lived together in Charlie’s beach house until he realized he was unwilling to be in a committed relationship.

Denise Richards as Lisa

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Denise Richards is a unique addition to this list, as she was married to Charlie Sheen in real life. They were married for four years, and have two daughters named Lola and Sam. The marriage has since ended, but Denise has enjoyed a successful career.

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Miley Cyrus as Missi

On his weekend leave from the Army, Jake meets Missi and quickly falls in love with her. The show reveals early on that although Missi may seem slightly odd, she is much smarter and kinder than most of the women on this list.

Miley Cyrus as Missi

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Miley Cyrus is one of the biggest celebrities to ever appear on the show, having already established herself as an actress and singer through her own Disney show, Hannah Montana. She’s recently released an album called Younger Now.

Source: YouTube

Megan Fox as Prudence

In season one, Berta ends up bringing her granddaughter, Prudence, to Charlie’s beach house to avoid leaving her alone.

Megan Fox as Prudence

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Arguably one of the biggest Hollywood stars on this list, Megan Fox continued to lead a successful career after her cameo on the show. She landed a role in Hope & Faith and was even cast in the incredibly successful Steven Spielberg film, Transformers.

Source: Wikipedia

Holland Taylor as Evelyn Harper

Arguably one of the funniest characters on the show, Evelyn Harper was Alan and Charlie’s neglectful mother. Evelyn’s complicated relationship with both of her sons, who tried their best to avoid her as much as possible, made for some great entertainment.

Holland Taylor as Evelyn Harper

Source: YouTube

Today, Holland Taylor is aged 75 and still well-recognized for famous television roles that include Ruth Dunbar in Bosom Buddies, Judge Roberta Kittleson in The Practice, and of course, Evelyn Harper-Pepper in Two and a Half Men.

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Jaime Pressly as Tammy

Tammy was a heavily tattooed girlfriend of Jake Harper, as well as the mother of three children. When she found out that Jake had sex with her daughter, Ashley, she was understandably heartbroken.

Jaime Pressly as Tammy

Source: Wikipedia

Jaime Pressly went on to achieve remarkable success in her career, arguably best known for her role as Lola Sombrero in The Oogieloves in the Big Balloon Adventure, for which she received two Emmy Award nominations, as well as a Golden Globe Award and a Screen Actors Guild Award!

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Allison Janney as Beverly

Beverly was a woman that Alan met on a dating network. In hopes of impressing her, Alan tricked her into thinking that the beach house was solely his – although he eventually admitted that it was, in fact, Charlie’s.

Allison Janney as Beverly

Source: Wikipedia

Revered for her versatility, Allison Janney has appeared in hit films such as Hairspray, Juno, and The Girl on the Train since the show. She’s won numerous accolades, including seven Primetime Emmy Awards, an Academy Award, a BAFTA Award, and a Golden Globe Award.

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Paget Brewster as Jamie Eckleberry

Growing up, Alan and Charlie knew Jamie Eckleberry as the chubby, unattractive girl with the nickname “Eckleberry hound.” It shocked them both when Jamie grew up to be stunning. They both try to hit on her, but she rejects both of them.

Paget Brewster as Jamie Eckleberry

Source: YouTube

Pagent Brewster went on to land the part of Kathy on the popular sitcom Friends. She then starred as Special Agent Emily Prentiss on the CBS crime drama Criminal Minds, appearing regularly from 2006 to 2012.

Source: Wikipedia

Kristin Dattilo as Cindy

Cindy was one of the characters that stood out for not getting into bed with Charlie. Unsurprisingly, Charlie didn’t take the rejection well. She ended up being Jake’s first “crush,” featuring in one of his erotic drawings.

Kristin Dattilo as Cindy

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Kristin Dattilo went on land a pivotal role as Yola Gaylen on The Chris Isaak Show. She also appeared on hit shows such as CSI: Crime Scene Investigation, Dexter, Beverly Hills, 90210, Friends, and Veronica Mars.

Source: YouTube

April Bowlby as Kandi

Because of her dashing looks and particularly large breasts, Kandi attracted the attention of many, including Charlie. Although she seemed sweet and somewhat innocent, she, of course, ended up having relations with Charlie – as well as Alan.

April Bowlby as Kandi

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April Bowlby is still very much active in her acting career, appearing in television series such as CSI, The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva. She also acted in films, including Love Me or Else, and Reunion.

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Maggie Lawson as Ms. McMartin

Ms. McMartin was the social worker who assigned Charlie and Alan a six-year-old African-American boy named Louis. However, when she realized that the “couple” deceived her, she instructed Louis to be removed from the house. In an attempt to change her mind, Alan slept with her.

Maggie Lawson as Ms. McMartin

Source: Wikipedia

As well as playing Juliet O’Hara in Psych, Maggie Lawson has kept up a successful career in television, appearing in shows such as Angel from Hell, Psych, and The Great Indoors. She’s also starred in the sitcoms Crumbs, Inside Schwartz, and It’s All Relative.

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Krista Allen as Olivia Pearson

Although she was a past girlfriend of Charlie’s, Olivia was formally introduced into the show when Charlie, Alan, and Jake visited their mother at a dinner – which ends prematurely when Olivia throws a drink in Charlie’s face.

Krista Allen as Olivia Pearson

Source: YouTube

Krista Allen is a comedian and actress best known for starring in television series Days of Our Lives and Baywatch. She’s also recognizable for her appearances in Hollywood blockbusters such as The Final Destinations and Anger Management.

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Jennifer Taylor as Chelsea Melini

Chelsea Melini was the first woman Charlie confessed his love to without being prompted. Though it’s said it was by accident, he later claims that he meant it. Although Chelsea was initially just another one-night stand, Charlie soon realized he was developing serious feelings for her.

Jennifer Taylor as Chelsea Melini

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Since, Jennifer Taylor, who’s married to Paul Taylor, has been involved in other television shows and films. Most recently, she appeared in the show Shameless but also has two upcoming shows still in post-production: Unfaithful and A Deadly Romance.

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Paula Marshall as Paula

After meeting at a nightclub, Paula and Alan seemed to hit it off. Eventually, Paula revealed that she was once a man named Paul. Fortunately for her, Alan didn’t seem to mind and continued to have a relationship with her.

Paula Marshall as Paula

Source: Wikipedia

Paula Marshall’s acting career continues to thrive, as she has appeared in hit shows such as House, Law and Order, Murder in the First, The Mentalist, and Switched at Birth. She’s also done some recent work for a film called “We Love You, Sally Carmichael!”

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Marin Hinkle as Judith Harper-Melnick

Judith was Alan’s first wife, daughter of Lenore and Sheldon, and the biological mother of Jake Harper and Milly Melnick. The marriage was so cold that Judith claims the only time she ever felt happy being sexual was when she was pregnant with Jake.

Marin Hinkle as Judith Harper-Melnick

Source: YouTube

Marin Hinkle, now aged 51, still has a successful acting career. As well as the series Madam Secretary on CBS, she also appeared on the shows Speechless and Homeland. Additionally, she just wrapped up a movie called Before/During/After.

Source: Wikipedia

Kimberly Williams-Paisley as Gretchen Martin

When Alan’s ex-girlfriend Lindsey eventually got engaged to another guy named Larry, Alan began dating his sister Gretchen. She becomes a recurring character in season 11, keeping a relationship with “Jeff Strongman.” This, apparently, was Alan’s alter-ego – an identity that Alan gets very into.

Kimberly Williams-Paisley as Gretchen Martin

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Kimberly Williams-Paisley is best known for her co-starring roles on Nashville and According to Jim. She has also made guest appearances on television shows, including Tales from The Crypt, George Lopez, and Less Than Perfect.

Source: Wikipedia

Missi Pyle as Miss Pasternak

Miss Pasternak was Jake’s fifth-grade teacher who suspended him. Shockingly, she began dating Charlie, who persuaded her to lift Jake’s suspension and give him good grades. However, when Charlie realized she was mentally ill, he broke up with her.

Missi Pyle as Miss Pasternak

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Actress Andrea Kay Pyle – more popularly known as Missi Pyle – has since appeared in several films, including The Artist, Big Fish, 50 First Dates, Charlie, and the Chocolate Factory, and Gone Girl. Currently, she’s working on many projects that are in the post-production process.

Source: YouTube

Liz Vassey as Kate McLaughlin

Kate, the pleasant single mother, was introduced to Charlie at Jake’s soccer game. She found it hilarious that Charlie appeared to look drunk, and the two hit it off. She later made another appearance on the show but as Charlie’s dermatologist, Michelle.

Liz Vassey as Kate McLaughlin

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After the show, Liz Vassey was cast in the web series Nikki & Nora. However, she’s best known for her role as Wendy Simms in CSI: Crime Investigation – a role she played for five continuous years!

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Justine Eyre as Gabrielle

Gabrielle was Charlie’s girlfriend until Alan decided to steal her out of revenge after finding out that it was Charlie who took his high school lover from him. Charlie obviously reacts badly to being betrayed by his own brother.

Justine Eyre as Gabrielle

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Canadian actress and model Justine Eyre made a few television appearances after the show: for example, on hit shows such as Mad Men, The Secret Life of the American Teenager, and CSI: Miami. She recently took a break from acting.

Source: YouTube

Rachel Cannon as Chloe

After dating Charlie for a while, Chloe was dumped for being too clingy. When she fell for Charlie’s handyman, Charlie decided to win her back. Out of jealousy, he makes the effort of showing up to the handyman’s house dressed up in trendy clothes.

Rachel Cannon as Chloe

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After the show, Rachel Cannon became widely known for her roles on Mad Men, The Big Bang Theory, and Fresh Off the Boat. As a result, the American actress is recognized around the world.

Source: Wikipedia

Brooke Shields as Danielle Stewart

Danielle, the party girl, was set up with Alan by Charlie. However, after she said to Charlie: “I’ve slept with a lot of guys and even a few women and even with couples,” the brothers end up fighting over Danielle, causing her to leave.

Brooke Shields as Danielle Stewart

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Brooke Shields was already a recognized actress and model before she appeared on the show, appearing in shows and films such as The Blue Lagoon, Endless Love, and NBC’s Law & Order: Special Victims Unit.

Source: YouTube

Sara Rue as Naomi

Naomi is Berta’s daughter, who her mother describes as “a little angel who swooped down from Heaven and landed on a married rich man’s penis.” She is introduced to the Harper brothers and develops a crush on Alan, which she conceals from her mother.

Sara Rue as Naomi

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After the show, Sara Rue became best known for her performances on the series Popular and Less than Perfect. She also hosted the reality series Shedding for the Wedding in 2011. Additionally, she’s appeared in The Big Bang Theory, Eastwick, and Rules of Engagement.

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Tammy Lauren as Shannon

Shannon is the ex-fiancée of Herb, Judith’s second ex-husband, who first met Alan at Herb and Judith’s wedding. Both of them were searching for the perfect revenge when they thought of the perfect idea – pretend to get intimate in their former lovers’ faces!

Tammy Lauren as Shannon

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Before appearing on the show, Tammy Lauren starred in the 1997 horror film Wishmaster. She also appeared as a regular on The Young and the Restless, a long-running soap opera. Recently, however, she has only appeared on one episode of Criminal Minds.

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Melanie Lynskey as Rose

Rose was initially someone who Charlie thought would be a one night stand. However, she ended up becoming his stalker. Later in the show, they got engaged and ran off to Paris together, but, unfortunately, Charlie’s character died before they were able to marry.

Melanie Lynskey as Rose

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Melanie Jayne Lynskey received numerous awards – including a New Zealand Film Award, a Hollywood Film Award, and a Sundance Special Jury Award – for the acting roles she has played since the show. She also received critical acclaim for her leading role in Hello I Must Be Going.

Source: YouTube

Kelly Stables as Melissa

Melissa, played by actress Kelly Stables, was a recurring character throughout the show, playing as Alan Harper’s receptionist. Eventually, Charlie was able to get her for himself until she began a relationship with Alan. Eventually, Melissa was humiliatingly dumped by Alan over a text.

Kelly Stables as Melissa

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Kelly Stables has since got married and now has a son. Additionally, she landed many acting roles throughout her career, including hit comedy movie, Horrible Bosses 2. Currently, she is working as a recurring character on the television show, Superstore.

Source: Wikipedia

Courtney Thorne-Smith as Lyndsey McElroy

A slightly masculine girl who enjoys drinking beer, Lyndsey kept popping up on the show as Alan’s on-and-off lover. Constantly deliriously drunk, her drinking problem became apparent when she was caught vomiting all over the interior of Walden’s private jet.

Courtney Thorne-Smith as Lyndsey McElroy

Source: YouTube

After five years of playing the role of Lyndsey on the show, Courtney Thorne-Smith took a break from Hollywood. Recently, however, she voiced a character on the animated series, Robot Chicken, and even appeared on ABC’s hit comedy show Fresh Off the Boat.

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Teri Hatcher as Liz

Liz is Judith’s sister and arguably seen as the “sleaze-ball” in the show. She is introduced for the first time at Jake’s birthday party and ends up having sex with Charlie in the coatroom during Alan and Judith’s wedding – although he does not remember.

Teri Hatcher as Liz

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Working on the show for eight years, Teri Hatcher won a Golden Globe Award, a Primetime Emmy nomination for Outstanding Lead Actress in a Comedy Series, and three Screen Actors Guild Awards. Afterward, she went on to star in the hit series Desperate Housewives.

Source: Wikipedia

Kimberly Quinn as Donna

Donna first met Alan on a blind date, and they were together for a while before Alan became bored. Not wanting to hurt her feelings, he asked advice from Charlie on how to dump Donna in the nicest way possible. Unsurprisingly, Charlie’s advice didn’t suffice.

Kimberly Quinn as Donna

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Proving to be as much of a force behind the camera as she is in front of it, Kimberly Quinn is renowned for engaging in acting, writing, producing, directing, and co-founding films with her husband, writer-director Theodore Melfi.

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Emmanuelle Vaugier as Mia

Mia was a dance teacher who initially had no interest in Charlie. However, when they got together, she made him give up eating meat, smoking, drinking and having sex. Charlie secretly continued all these activities behind her back.

Emmanuelle Vaugier as Mia

Source: Wikipedia

Canadian actress, singer, and model Emmanuelle Vaugier secured several acting jobs after her appearance on the show, such as television shows Lost Girl and Mistresses. She recently starred in Killer Ending, and is set to appear in My Mother’s Stalker, Masks Don’t Lie and Don’t Look There.

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Ming-Na Wen as Linda Harris

Linda Harris, a judge whom Charlie dated for a brief period, first entered the show after Alan planned a double date involving his brother. Although Charlie was fond of her, Linda actually found him repulsive due to his lecherous nature.

Ming-Na Wen as Linda Harris

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Ming-Na-Wen was the voice of the Disney character Mulan, as well as Melinda May in the ABC action drama series Agents of S.H.I.E.L.D., and Dr. Jing-Mei Chen in medical drama series ER.

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Judy Greer as Bridget Schmidt

Ashton Kutcher’s character was genuinely heartbroken over his divorce from Bridget, who initially refused to reconcile with him due to his immaturity. Changing her mind, she returned to the beach house begging for him to take her back, to which Walden responded with the finalization of their divorce.

Judy Greer as Bridget Schmidt

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Judy Greer has an astoundingly long filmography list. The actress, director, model, and author is well-known as a character actor, appearing in a wide variety of dramatic and comedic films.

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Stephany Jacobsen as Penelope

After Charlie’s death, Alan moves out when Walden purchases the beach house. One night, Alan revisits the house to clean some of his clothes when a woman named Penelope suddenly enters. In hopes of seeing Charlie, she becomes distraught upon hearing about his death.

Stephany Jacobsen as Penelope

Source: Wikipedia

After the show, Stephany Jacobsen, a Hong Kong-born Australian actress, appeared in movies such as Battlestar Galactica: Razor and Alex Cross. Though she went on an acting hiatus in 2014, Stephany made an appearance in the movie Occupation in 2018.

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Jeri Ryan as Sherri

Sherri was the kind of girl that serial womanizer Charlie had never encountered before. She played hard to get, constantly leading Charlie on. However, because he was considered the one being used, Charlie decided he wanted to seek revenge. This ultimately led to their downfall.

Jeri Ryan as Sherri

Source: Wikipedia

Jeri Ryan is a German-born American actress who is best known for her role on Star Trek: Voyager, for which she received four nominations for a Saturn Award. She is also known for her performances on television series such as Boston Public, Dark Skies, and Shark.

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Sophie Winkleman as Zoey Hyde-Tottingham-Pierce

Zoey was the gorgeous British ex-girlfriend that Walden was serious about after his divorce from Bridget. After dating for two seasons, Zoey rejected his marriage proposal. Walden then discovered that Zoey had been dating another man and decided to seek revenge.

Sophie Winkleman as Zoey Hyde-Tottingham-Pierce

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Interestingly, Sophie Winkleman is the wife of Lord Frederick Windsor, son of Prince Michael of Kent, Queen Elizabeth II’s first cousin. Consequently, she’s actually known as Lady Frederick Windsor. Currently, she’s filming a new show called Trust, featuring Donald Sutherland and Hilary Swank.

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Conchata Ferrell as Berta

The cynical, sharp-tongued, sassy, hard-working character of Berta, the housekeeper, was probably the only woman in the show that Charlie didn’t develop feelings for. However, she offered a lot of comic relief for the audience.

Conchata Ferrell as Berta

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Conchata Ferrell has received two Primetime Emmy Award nominations for her exceptional performances. The American actress is still active in the industry, with the role of Shirley on Netflix comedy show The Ranch. She was also in the film Deported.

Source: Wikipedia

Heather Locklear as Laura

As Alan and Judy were going through their divorce settlement, Charlie slept with Alan’s attorney, Laura Lang. Because Charlie broke his promise of making himself available to her whenever she wanted, Laura took revenge by ruining Judith and Alan’s divorce proceedings.

Heather Locklear as Laura

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Heather Locklear was already an accomplished television actress before her appearance on the show, renown for roles in Spin City and Melrose Place. Since a very publicized divorce and numerous health issues, she has appeared in Franklin & Bash and Tyler Perry’s Too Close to Home.

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Jenny McCarthy as Courtney Leopold

Courtney Leopold was a former professional con-artist who eventually became Charlie’s temporary girlfriend. Alan warned Charlie of Courtney’s sociopathic tendencies, but to no avail. Alan is, of course, proven right after Courtney successfully convinces Charlie to give her $50,000 and give her a Ferrari.

Jenny McCarthy as Courtney Leopold

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Jenny McCarthy, sometimes credited as Jenny Wahlberg, is an actress, activist, model, television host, author, screenwriter, and former Playboy magazine model. She even won Playmate of the Year! She went on to appear in films such as Scream 3 and Santa Baby.

Source: heraldweekly.com