Gail O’Grady as Mandi
Two and a Half Men is an American sitcom that aired on CBS for 12 seasons from September 2003 to February 2015. In the eighth season, CBS producers and star Charlie Sheen had a very public falling out, resulting in Sheen being written off the show and being replaced with actor Ashton Kutcher.
With its many dating escapades of characters Charlie, Alan, and Walden, there had been a number of female characters, usually in one-episode stints. The show’s popularity grew as viewers tuned in weekly to see which famous actress Charlie would date next. With this compilation of women who appeared on this show – both then and now – how many faces will you recognize?
Emmanuelle Vaugier as Mia
Mandi is Kandi’s mother and Andy’s ex-wife. One day, Mandi went to Charlie’s House to look for Kandi. Kandi and Mandi looked so much alike that strangers mistook them for sisters. Jake made a joke about how Mandi could be his stepmother, stepsister, and step-cousin all at the same time.
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 been married six times. She has one son with an ex-boyfriend, Chris Byers.
Jennifer Taylor as Chelsea Melini
Mia, a dance teacher, convinced Charlie to give up his unhealthy habits, but he continued them secretly. They became engaged on the show and went to Vegas to get married, but their relationship ended when Mia learned that Alan wasn’t moving out. This is also the episode where Alan and Kandi got married using the ring left over from Charlie’s previous breakup.
French-Canadian actress, singer, and model Emmanuelle Vaugier secured several acting jobs after her appearance on the show, such as the television shows Lost Girl and Mistresses. She also starred in CSI: NY, Smallville, Human Target, and Lost Girl.
Denise Richards as Lisa
Chelsea Melini was the first woman Charlie confessed his love 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, married to Paul Taylor, has acted in TV and film, including Shameless. She has two upcoming shows, Unfaithful and A Deadly Romance, and resides in Los Angeles with her family. She moved from Hoboken, NJ to Coral Springs, FL before settling in LA. Before Two and a Half Men, she competed in Miss Florida UA pageants.
Missi Pyle as Miss Pasternak
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. She was around for three episodes before leaving the show.
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 had two daughters named Lola and Sam. The marriage has since ended, but Denise has enjoyed a successful career. Richards adopted Eloise Joni Richards, her third daughter, back in 2011. In 2018, she got married to Aaron Phypers.
Kelly Stables as Melissa
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.
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. Pyle was married to Antonio Sacre and Casey Anderson before. She also appeared in the 2 Broke Girls and worked on several projects in post-production, including a role in the show Mom.
Marin Hinkle as Judith Harper-Melnick
Kelly Stables played Melissa, Alan Harper’s receptionist and Charlie’s girlfriend. After she started a relationship with Alan, he dumped her over text. In season eight, Alan secretly gets intimate with her at Charlie’s house despite being in a relationship with Lyndsey. Melissa does not appear in any episodes after that.
Kelly Stables has since got married and now has a son. Additionally, she landed many acting roles throughout her career, including the hit comedy movie, Horrible Bosses 2. She’s also known for her role as Kelly in Superstore and Eden Konkler on The Exes.
Allison Janney as Beverly
Judith was Alan’s first wife and the mother of Jake Harper and Milly Melnick. The marriage was unhappy; Judith even lied about being gay to end it. She later remarried Jake’s pediatrician, Herb. Alan was only happy about this because it meant he no longer had to pay alimony.
Even after her role in Two and a Half Men, Marin Hinkle continued to have a successful acting career. She appeared on the shows Speechless and Homeland, including the series Madam Secretary on CBS. She’s also known for playing Judy Brooks on the ABC television drama Once and Again. In 2019 and 2020, she was nominated for Primetime Emmy Awards for Outstanding Supporting Actress in a Comedy Series.
Brooke Shields as Danielle Stewart
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.
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. She was also the main character on the show Mom.
Kimberly Williams-Paisley as Gretchen Martin
Charlie set up Danielle, who enjoyed drinking, and disclosed to him that she had slept with many men, women, and couples, with Alan. The brothers fought over Danielle, but she revealed that she wanted to sleep with both of them. This caused them to lose interest in her entirely.
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. Shields has been married twice, and she is married to Chris Henchy since 2001. They have two daughters, Grier Hammond and Rowan Francis.
Judy Greer as Bridget Schmidt
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.
Brad Paisley played Gretchen’s fiancé in the show and is also her real-life husband. They have two sons together, William Huckleberry and Jasper Warren, named after Paisley’s grandfather who bought him his first guitar. Kimberly Williams-Paisley co-starred in Nashville and According to Jim and has guest-starred in several television shows.
Holland Taylor as Evelyn Harper
Ashton Kutcher’s character was genuinely heartbroken over his divorce from Bridget, who initially refused to reconcile with him due to his immaturity. She eventually changed her mind and returned to the beach house, begging for him to take her back. Walden responded to her with the finalization of their divorce and tried to continue his relationship with Zoey.
Judy Greer played Herb’s sister, Myra, and had drama with Charlie and Alan. She also appeared as Bridget Schmidt in the final episode, lying in bed with John Stamos. Greer is a well-known character actor with a long list of film credits that span both drama and comedy.
Arguably one of the funniest characters on the show, Evelyn Harper, was Alan and Charlie’s neglectful mother. Evelyn had a difficult relationship with her sons, who avoided her as much as possible. They saved her phone number under ‘666’ and called her ‘the devil’. Evelyn also lied about her age to seem younger. While she wasn’t too close to her two sons, she loved her grandson Jake.
For her role in Two and a Half Men, she received a total of four Primetime Emmy Award nominations and is well-recognized for famous television roles that include Ruth Dunbar in Bosom Buddies and Judge Roberta Kittleson in The Practice.
Justine Eyre as Gabrielle
Gabrielle was Charlie’s girlfriend, but Alan stole her as revenge for Charlie taking his high school sweetheart. However, Alan discovered that Gabrielle had unusual behavior in bed, which he did not like. Charlie knew about this but continued to date Alan’s ex. This all happened in the episode where Jake’s girlfriend broke up with him.
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 and is now an Audie-winning narrator with over 650 titles.
Sophie Winkleman as Zoey Hyde-Tottingham-Pierce
Zoey was Walden’s beautiful British ex-girlfriend. He confided in her about his depression after his divorce from Bridget. Despite Zoey wanting to end things, Walden insisted that he was over his ex-wife. However, after dating for two seasons, Zoey rejected Walden’s marriage proposal. He later found out that Zoey had been seeing someone else and sought revenge.
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.
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. Lyndsay is Jake’s best friend, Eldridge’s mom. Their secret relationship was quickly discovered by the kids. Her drinking problem was revealed when she vomited inside Walden’s private jet while constantly drunk. Lyndsay was a recurring character and dated Alan intermittently.
After five years of playing the role of Lyndsey on the show, Courtney Thorne-Smith took a break from Hollywood. However, she later returned and voiced a character in the animated series Robot Chicken in 2016. She also appeared on ABC’s hit comedy show Fresh Off the Boat and CBS’s Mom.
Megan Fox as Prudence
In season one, Berta ends up bringing her granddaughter, Prudence, to Charlie’s beach house to avoid leaving her alone. Prudence’s gorgeous looks and incredible figure leave all the men, including Jake, completely smitten.
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 starred in ABC’s Hope & Faith, but her breakout role in the blockbuster action film Transformers as Mikaela Banes.
Jaime Pressly as Tammy
Tammy, Jake Harper’s tattooed girlfriend and mother of three, met him through her parole officer. They once dressed up as her three baby daddies for Christmas and almost got married in Vegas. However, when Tammy discovered that Jake had been with her daughter, Ashley, she was understandably heartbroken. Jake was going to date Ashley until her ex-boyfriend proposed to her at the end of the season.
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.
Paget Brewster as Jamie Eckleberry
Growing up, Alan and Charlie knew Jamie Eckleberry as the chubby, unattractive girl with the nickname “Eckleberry hound.” The three of them were high school classmates. It shocked them both when Jamie grew up to be stunning. They both try to hit on her, but she rejects them both.
Brewster also Kathy on Friends and Emily Prentiss on Criminal Minds. She married Steve Damstra in 2014, with Matthew Gray Gubler, her co-star on Criminal Minds, officiating the ceremony. Did you know that she was also approached with a handwritten note from Hugh Hefner asking her to pose for Playboy? Despite her interest and her parents’ support, she eventually turned it down.
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 went on land a pivotal role as Yola Gaylen on The Chris Isaak Show. She also had small roles in many popular TV shows including CSI: Crime Scene Investigation, Dexter, Beverly Hills 90210, Friends, Angel, and Veronica Mars. Dattilo is the sister of Bryan Dattilo, known for his character on Days of Our Lives.
April Bowlby as Kandi
Because of her dashing looks and particularly large breasts, Kandi attracted the attention of many, including Charlie. Despite appearing sweet and innocent, she had relationships with both Charlie and Alan. Kandi and Alan married despite their relationship being based on superficial things. Though Alan was eventually kicked out for not wanting to have a child with her.
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, Psych, Mom, You’re the Worst and Drop Dead Diva. She also starred in Titans and Doom Patrol.
Maggie Lawson as Ms. McMartin
Ms. McMartin was the social worker who assigned Walden and Alan a six-year-old African American boy named Louis. Alan and Walden pretended to be gay for the adoption to work in their favor. After being deceived by the couple, she kicked Louis out. Alan slept with her to try and change her mind, realizing he loved her. He used Michael Bolton to get her back and succeeded.
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 was also a recurring cast on Fox’s Lethal Weapon’s third and final season and starred in the sitcoms Crumbs, Inside Schwartz, and It’s All Relative.
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 – and their relationship ends prematurely when Olivia throws a drink in Charlie’s face.
Krista Allen is a comedian and actress famous for her roles in Days of Our Lives, Baywatch, The Final Destinations, and Anger Management. She also appeared in the Friends episode The One Where Joey Dates Rachel as Joey’s girlfriend. Allen has been married twice and has a son named Jakob Nolan Morritt from her first marriage.
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 also appeared in popular TV shows such as House, Law and Order, Murder in the First, The Mentalist, and Switched at Birth. She was also in the movie Cheaper by the Dozen and We Love You, Sally Carmichael! She has been married to Danny Nucci since 2003, and the couple has a daughter named Maya Nucci.
Liz Vassey as Kate McLaughlin
Kate, a single mother, met Charlie at Jake’s soccer game where they hit it off despite Charlie appearing drunk. She later appeared on the show as Charlie’s dermatologist, Michelle, in three different episodes, each time playing a different character. The episodes include The Last Thing You Want Is to Wind Up With a Hump, Twanging Your Magic Clanger, and The Crazy Bitch Gazette.
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! She’s married to David Emmerichs, who is a camera operator, since 2004.
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 at the handyman’s house dressed up in trendy clothes.
Rachel Cannon rose to fame for her roles in Mad Men, The Big Bang Theory, and Fresh Off the Boat. She runs a blog called Rachel Cannon: Behind the Scenes, which focuses on her life, and writes about her experience with a faith-based short film that she stars in, produced, and co-wrote.
Sara Rue as Naomi
Naomi, Berta’s daughter, develops a crush on Alan but keeps it secret from her mother. Berta takes Charlie to confront the father of Naomi’s baby. Alan spends time with Naomi and reveals his pregnancy fetish. However, the man they confront is not the father.
After the show, Sara Rue became best known for her performances in 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.
Miley Cyrus as Missi
On a weekend leave from the Army, Jake falls in love with an old family friend named Missi. Despite her seeming odd, Missi is portrayed as smarter and kinder than most women on the show. However, Jake’s feelings are not reciprocated and Missi breaks up with him in season ten, episode seven.
Miley Cyrus, known for her role in the Disney show Hannah Montana, is a popular celebrity who recently released an album called Younger Now. She was married to Liam Hemsworth for a year from 2018 to 2019 after meeting him on the set of The Last Song in 2010, but the two have since divorced in 2020.
Tammy Lauren as Shannon
Shannon, the ex-fiancée of Judith’s second ex-husband Herb, met Alan at Herb and Judith’s wedding. Although Charlie was dating Herb’s sister at the time, Alan and Shannon were interested in each other. They started a relationship, but it moved too quickly for Alan, and he wanted to slow things down. Shannon was unhappy about this and made fake sounds of them having sex.
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, and on one episode of Criminal Minds.
Melanie Lynskey as Rose
Charlie initially thought Rose would be a one-night stand, but she became his stalker. They got engaged and ran off to Paris. She appears frequently and meets Walden, becoming his stalker after Charlie’s supposed death. In the finale, it’s revealed that she had been keeping Charlie in her basement the whole time, and he didn’t really die in the train accident.
Melanie 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. From her role in Yellowjackets, she won the 2022 Critics’ Choice Award for Best Actress in a Drama Series.
Teri Hatcher as Liz
Teri Hatcher played Liz, Judith’s sister, and is arguably seen as one of the “sleaze-balls” in the show. She is introduced for the first time at Jake’s birthday party and ends up with Charlie in the coatroom during Alan and Judith’s wedding – although he doesn’t remember it.
Hatcher is probably best known for her portrayal of Lois Lane on Lois & Clark: The New Adventures of Superman, as well as being on the show Desperate Housewives, for which she won a Golden Globe Award. She also had a memorable guest-starring role on Seinfeld. In the last few years, Hatcher has gotten into baking.
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 for advice from Charlie on how to dump Donna in the nicest way possible. Unsurprisingly, Charlie’s advice didn’t suffice.
Kimberly Quinn is a multi-talented artist known for acting, writing, producing, directing, and co-founding films with her husband, Theodore Melfi. She has appeared on TV shows like Cold Case, CSI: NY, The Secret Life of the American Teenager, and Grey’s Anatomy. She also starred in the acclaimed film Hidden Figures as Ruth.
Ming-Na Wen as Linda Harris
Charlie briefly dated Linda Harris, a judge who Alan tried to set him up with. Despite Charlie’s fondness for her, Linda found his behavior repulsive. After Charlie was arrested for a DUI, Linda became his judge and fined him $500.
Charlie sang a song to Linda’s son to help him in the bathroom and was given a job writing children’s songs by Linda’s ex-husband, but they broke up after Charlie embarrassed himself at Linda’s rewards show due to taking a pill to relax. But did you know Ming-Na-Wen was the voice of the Disney character Mulan? She also starred in ABC’s Agents of S.H.I.E.L.D. and in the Star Wars franchise The Mandalorian.
Stephany Jacobsen as Penelope
After Charlie’s death, Alan moves out of the beach house when Walden buys it. One night, he returns to the house to get his clothes and encounters Penelope. She had hoped to see Charlie and was upset to hear about his death. Walden and his wife, Bridget, arrive to talk to Alan. To avoid any conflict, Alan pretends to be Penelope’s boyfriend, and the two women leave shortly after.
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.
Jeri Ryan as Sherri
Sherri was a girl who played hard to get and led serial womanizer Charlie. He sought revenge because he felt used, but this caused their downfall. Sherri was similar to Charlie and almost dated Alan, but he didn’t like that she had been with Charlie. She eventually got tired of the lifestyle and stopped appearing on the show.
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. From 2020 to 2023, she reprised her role as Seven in Star Trek: Picard. She is also known for her performances on television series such as Boston Public, Dark Skies, and Shark.
Heather Locklear as Laura
During Alan and Judy’s divorce settlement, Charlie slept with Alan’s attorney, Laura Lang. Laura sought revenge by sabotaging the proceedings, leading to Alan firing her and nullifying her decisions. This was unfair as Charlie was the one at fault.
Heather Locklear was already an accomplished television actress before her appearance on the show, renowned 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. Locklear was previously married to Tommy Lee, the Motley Crue drummer, and then she married Bon Jovi guitarist Richard Sambora.
Jenny McCarthy as Courtney Leopold
Courtney Leopold, a former con artist, briefly dated Charlie despite Alan’s warning about her sociopathic tendencies. Charlie later gave her $50,000 and a Ferrari, proving Alan right. Sylvia Fishman was her real name. Evelyn’s fiancé, Teddy, was also a con artist named Nathan Krunk, who worked with Sylvia. In their last appearance, Nathan passes away due to a heart attack while in bed with Sylvia.
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! Since 2019, McCarthy has been a judge on the Fox musical competition show The Masked Singer.
Hilary Duff As Stacey
Stacey came along in the show for one episode in Season 10. Even though she earned a communications major at Arizona State, she couldn’t hold a conversation. Duff played the ditzy one-night stand of Walden’s with likable ease.
Hilary Duff began her career early and became a teen idol for her role in the TV series and movie, Lizzie McGuire. From 2015 to 2021, Duff starred in TV Land’s longest-running original series Younger, for which she received two People’s Choice Awards nominations. Since 2022, she has produced and starred as Sophie Tompkins in the Hulu sitcom How I Met Your Father.
Mila Kunis As Vivian
Mila Kunis made a cameo as Vivian, a free-spirited hiker, and the love interest of Ashton Kutcher’s character Walden. Walden was going to propose to his girlfriend in Season 10 but met Vivian instead. That ’70s Show’s Jackie and Kelso also appeared onscreen together, with a nod to the show. Although Vivian isn’t seen again, it was a great moment for fans.
In 1991, when Kunis was seven, she moved from Soviet Ukraine to the US with her family. After enrolling in acting classes as an after-school activity, she was discovered by an agent. She is currently married to Ashton Kutcher and have two kids together.
Jenna Elfman as Frankie and as Dharma Montgomery
On Season 1, her character Frankie was more of an afterthought. But years later, Elfman came back in Season 9 to play her character Dharma from the beloved sitcom, Dharma & Greg. It was a perfect collision of sitcom worlds.
Elfman is a TV comedy actress. She had her first leading role in the 1996 sitcom Townies, followed by her movie debut in 1997’s Grosse Pointe Blank. She is married to Bodhi Elfman, whom she met at a Sprite commercial audition, and they have two sons. Elfman is a member of the Church of Scientology and co-hosted a charity event with Charlie Sheen at the Geisha House in Hollywood in 2008.
Kathy Bates As Charlie Harper’s Ghost
Kathy Bates played Charlie’s ghost. She came to visit Alan in the hospital and explained to him, “I’m in hell. Walking around in this old broad’s body is supposed to be some kind of eternal damnation. You know what? Jokes on them. Boobs are still boobs!”
The actress Kathy Bates has won many awards, including an Academy Award, three American Comedy Awards, two Emmy Awards, two Golden Globe Awards, an Obie Award, and two Screen Actors Guild Awards. She has appeared in many popular movies and shows, including P.S. I Love You, The Blind Side, and The Office.
Janeane Garofalo as Sharon
Janeane Garofalo guest-starred as Sharon in a season 5 episode called “Media Room Slash Dungeon.” In the episode, Alan goes to bed with this new woman, Sharon, who has self-esteem issues. Garofalo has become an outspoken progressive activist. From March 2004 to July 2006, she hosted a show called Air America Radio’s The Majority Report with Sam Seder.
She has appeared in over 50 movies and was part of the cast of popular TV shows such as The Ben Stiller Show, The Larry Sanders Show, and Saturday Night Live. She married one of the writers from The Ben Stiller Show, Robert Cohen, as a joke, but they later realized it was a real marriage when Cohen tried to get married again. They dissolved the marriage in 2012.
Mimi Rogers as Robin
In the season finale episode “A Chic Bar in Ibiza,” Mimi Rogers played Walden Schmidt’s mother Robin. She visited for Christmas and, with Bridget’s help, took over Walden’s company. Alan joined forces with Walden to fight back, but the girls tried to bribe Alan with a Porsche. When that didn’t work, they attacked him instead.
Rogers is a multi-talented professional, excelling in film, TV, and poker. Her noteworthy film roles include Gung Ho, Someone to Watch Over Me, and Desperate Hours. She has been married three times: to James Rogers, Tom Cruise (for only two years), and Chris Ciaffa, with whom she has two children.
Conchata Ferrell as Berta
Berta, the housekeeper in the show, was a sharp-tongued and sassy character who provided comic relief for the audience. Despite having three daughters, she constantly involved Charlie and Alan in her family life, often bringing her children and grandchildren around. In one instance, she even quit her job in order to get Charlie to stop seeing a woman she didn’t like.
Conchata Ferrell has received two Primetime Emmy Award nominations for her exceptional performances. She was also previously nominated for the Primetime Emmy Award for Outstanding Supporting Actress in a Drama Series for her performance in L.A. Law. Unfortunately, she passed away in 2020 due to complications following cardiac arrest.
Cloris Leachman As Nora
In an effort to change up the “sugar daddy” trope, Alan dated Norma, a much older, richer woman in Season 3. It sounded promising but ended up being a bad decision when she passes away in the middle of having relations with Alan.
Cloris Leachman, the actress who plays Norma, is also a comedian. In a career of more than seven decades, she has won eight Primetime Emmy Awards, a Daytime Emmy Award, and an Academy Award for her role in The Last Picture Show. In 2021, Leachman sadly passed away due to a stroke and COVID-19. Now that we’ve covered all these amazing women, it would be unfair to leave out some of the guys, right…?
Gary Busey
The Academy Award nominee made a short cameo in the Season 9 episode called “Frodo’s Headshots” as a patient in the psych ward. It’s where Alan wound up following a mental breakdown triggered by Charlie’s shenanigans.
Busey has appeared in 150+ movies, including Lethal Weapon, Predator 2, Point Break, Under Siege, The Firm, Carried Away, Black Sheep, Lost Highway, Fear and Loathing in Las Vegas, The Gingerdead Man, Quigley, and Piranha 3DD. He has a daughter named Alectra and a son named William Jacob “Jake” Busey from a previous marriage. He is engaged to Steffanie Sampson, with whom he has a son named Luke Sampson.
Jason Alexander
George from Seinfeld guest stars in Two and a Half Men as Dr. Goodman, Alan’s cardiologist in the 200th episode. Alan, who had a heart attack, gets a clean bill of health from Dr. Goodman but pretends he may need a heart transplant. This obviously didn’t go well, and Zoey ends up catching him in the lie.
His real name is Jason Greenspan, but he adopted the stage name Jason Alexander while in high school in New Jersey. He appeared in Broadway plays and movies, then in the hit TV series, Seinfeld, from 1990 to 1998. Along with directing and producing films, he can be seen in the Cinderella movie starring Brandi. He plays the right-hand man to the prince.
Elvis Costello and Sean Penn
In the Season 2 premiere, Back Off Mary Poppins, a support group for men is featured. Alan, Charlie’s brother, wants to join the exclusive club but is turned away. He makes an attempt to contact them on his own, which leads to one of his exes turning the guys against him. Eventually, Alan is let into the group but becomes too annoying and is tied to a street lamp. This episode’s title is delivered by Sean Penn.
Penn won two Academy Awards for his roles in Mystic River and Milk. He began his acting career in TV, with a brief appearance in Little House on the Prairie, directed by his father, Leo Penn. Penn’s net worth is approximately $150 Million dollars.
Michael Clarke Duncan
The late actor played Jerome, a retired football player and intimidating new neighbor in Season 6. Charlie covered for his nephew when he went on a date with Jerome’s daughter, Celeste Burnette. Jerome asked Charlie to check on them when they were late returning from a walk on the beach. Charlie couldn’t reach Jake as he had left his phone at home and had to listen to Jerome’s over-protective rants.
Sadly, Duncan passed away on July 13, 2012, as he was taken to Cedars Sinai Medical Center after suffering a heart attack. It is said that his girlfriend tried to perform CPR to save his life. He spent a bit of time in the ICU before passing away. The actor was only 54 years old.
John Stamos
Uncle Jessie made an appearance in Kutcher’s debut episode as a potential beach-house buyer, but he backed out after remembering a drunken threesome with Charlie. Stamos also shows up for the last episode of the whole show. Bridget, Walden’s ex-wife, called him up, and you can see her lying in bed with Stamos.
John Stamos rose to fame as Blackie Parrish in General Hospital, earning a Daytime Emmy nomination for Outstanding Supporting Actor in a Drama Series. He is currently married to Caitlin McHugh and has a son named Billy. Stamos is a big Elvis Presley fan and often referenced him during his role as Uncle Jesse in Full House.
Jon Lovitz
Jon Lovitz guest-starred as Charlie’s jingle-writing enemy, Archie Baldwin, in the Season 3 episode titled “The Unfortunate Little Schnauser.” Baldwin had a history of beating Charlie out for advertising awards. He did it again in this episode by singing ‘Save the Orphans’ and winning the award for the best jingle writer.
Lovitz is best known for his time on Saturday Night Live from 1985 to 1990. He also appeared in The Critic and other TV series and movies, including a memorable appearance on Friends. Did you know that Jon Lovitz has an ongoing feud with Andy Dick over an old friend? While they fight and make up a lot, in 2007, he smashed Dick’s head into a bar.
Enrique Iglesias
The hugely popular Latin singer also appeared in the show’s fourth season. He portrays a handsome handyman named Fernando, who Charlie called after his deck collapsed with him on it. Fernando ended up winning Charlie’s girlfriend’s affection, as well as Berta’s. Charlie fired Fernando and then slept with Chloe to celebrate. The episode ends with Charlie falling off the deck.
Enrique is widely regarded as the King of Latin Pop. He sold over 100 million records (both albums and singles combined) worldwide, which made him one of the best-selling Spanish-speaking artists ever. Enrique Iglesias has a relationship with Anna Kournikova, a Russian tennis player. The couple reportedly had twins at South Miami Hospital in 2017.
Chris O’Donnell
In a Season 1 episode, the NCIS: Los Angeles star played a former friend of Charlie’s, Jill. Charlie goes to meet his old friend Jill at the bar and learns that Jill is now a trans man named Bill. Evelyn meets Bill, and the two hit it off. Of course, Berta gets a kick out of the whole situation being as Charlie dated him as Jill, and now Bill is into his mother.
O’Donnell was discovered when he was cast in a McDonald’s commercial, where he served Michael Jordan! His first TV role was an appearance on the series Jack and Mike in 1986. Chris O’Donnell is married to Caroline Fentress since 1997, and they now have five kids.