The American television sitcom, “Two and a Half Men”, really solidified its place as the cream of the crop for the periods of the show’s exceptional success. It performed so well on CBS that the network let it run for an astounding twelve seasons, ending in 2015.
On the eighth season CBS felt that a break was needed after Charlie Sheen got into drug rehabilitation and made some “disparaging comments” about the show’s creator and executive producer. The series continued after the break with the addition of a new main character played by well-known Hollywood superstar, Ashton Kutcher.
The fact that so many beautiful woman participated on the iconic series is pretty ironic considering the title “Two and a Half Men”, it definitely wouldn’t have been nearly as entertaining or funny without them.
Such entertainment brought audiences to turn in week after week, curious to find out which famous woman actress Charlie would target next, adding some elements of drama and insanity every now and then. we’ve prepared a list of some of the best (and worst) women that made appearances on the show and where they are today!
Jennifer Taylor as Chelsea Melini | Then
Chelsea Melini had the great honor of being the first woman Charlie ever confessed his love to without any prompting. Though he says it nearly by accident, he still claims that he meant it later on. In the beginning, Charlie just saw Chelsea as another one-night stand but along the way, he realized he was developing serious feelings for her.
After a pretty rocky relationship, Charlie decides to prove his love for her by proposing, thinking that he can get her to say “I love you” back to him. Unfortunately, Chelsea ends up leaving him for Alan’s lawyer. What a blow to the ego!
Jennifer Taylor as Chelsea Melini | Now
The American actress, now married to Paul Taylor, continued on with her acting career after her appearance on the show, subsequently being involved in other television shows and films. Most recently, she appeared the Shameless, a series focusing on a fiercely loyal Chicago family.
She also has two upcoming shows still in post-production, Unfaithful and A Deadly Romance.
Holland Taylor as Evelyn Harper | Then
Arguably one of the funniest characters on the show, Evelyn Harper, played by Holland Taylor, was Alan and Charlie’s neglectful mother. The show exhibited Evelyn’s difficult relationship she had with both of her sons who tried their best to avoid her as much as possible. Such tension in the show really made for some great entertainment, having viewers busting their guts laughing.
The script writes also made sure to add some more bang to her character by making her that woman who got with older men for their money and assets.
Holland Taylor as Evelyn Harper | Now
Today, Taylor is powering through the age of 75, 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.
With her exceptional talent, she continues to nail acting jobs across the industry such as roles in The Orville, Hollywood Mom, and Mr. Mercedes.
Kelly Stables as Melissa | Then
Melissa was the recurring character throughout the show, playing as Alan Harper’s receptionist. Eventually, Charlie was able to get her to all for him until she began a relationship with Alan.
The two eventually encounter some tribulations when Melissa finds out that Alan is lying about renting a home. Eventually, Melissa is humiliatingly dumped after Alan decides to end the toxic relationship for good over a text.
Kelly Stables as Melissa | Now
Kelly Stables has landed a tremendous amount of acting roles over the course of her career. She even appeared in the hit comedy movie, Horrible Bosses 2, starring Jason Bateman, Charlie Day, Jason Sudeikis, and Steve Wiebe.
She is currently working as a recurring character on the television show, Superstore, an American sitcom that follows the lives of a group of employees working at a fictional big-box store in Missouri. She is also enjoying the married life with her husband, Kurt Patino, both raising their only son.
April Bowlby as Kandi | Then
Kandi is the young woman portrayed as a 22-year-old dumbbell. Though she may seem sweet and somewhat innocent, Kandi is pretty dense and loves to sleep with older men, like Charlie Harper, of course. Because of her dashing looks and particularly large breasts, Kandi gets the attention of many, including Charlie.
She ends up finding her way into not just Charlie’s arms, but those of Alan’s and Alan’s former lawyer as well! She ends up choosing and marrying Alan in Vegas but eventually breaks up with him after accepting a role as an investigative reporter on a television show titled “Stiffs”. Although, Alan’s nose hair and ear hair were probably among her reasons for her leaving him.
April Bowlby as Kandi | Now
April Bowlby is still very much active in her acting career, much like many of the other women on the list. She appeared on many television series that includes CSI, The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva. She also has done some work in films such as Love Me Or Else and Reunion.
Aside from her drop-dead looks, the actress also gained some popularity over her relationship with the well-known singer, Josh Groban.
Courtney Thorne-Smith as Lyndsey McElroy | Then
Coming off as the slightly masculine girl who enjoys drinking beer, Lyndsey was the character that 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. Yikes!
Though she has deep care and love for Alan, Lyndsey is seen as a considerably flirty, lusting after men including Walden, played by Ashton Kutcher.
Courtney Thorne-Smith as Lyndsey McElroy | Now
After five years of playing the role of Lyndsey on the show, Courtney Thorne-Smith took a break from the fast paced-lifestyle of Hollywood. Although, she recently voiced a character on the animated series, Robot Chicken, and even appeared on Fresh Off The Boat, ABC’s hit comedy show.
Aside from her acting career, Thorne-Smith enjoys spending her time with her husband, Roger Fishman, and their son, Jacob.
Megan Fox as Prudence | Then
In the season 1 episode, Berta shares that she can’t leave her granddaughter, Prudence, alone in a house and ends up bringing her to Charlie’s beach house. Her gorgeous looks and sexy figure leaves all of the men, including Jake, completely smitten.
She then comes back in the night after a dispute with her grandmother, surprising Charlie, Alan, and Jake with her shocking plans of eloping with her boyfriend to get married in Vegas. Her plan is eventually dismantled when her mother Cheryl Ann interrupts the ordeal.
Megan Fox as Prudence | Now
Probably one of the biggest stars on this list, Megan Fox continued on to a remarkable career with her major success in Hollywood after her cameo on the show. She was able to land a role in Hope & Faith and was even cast in the extremely famed Steven Spielberg film, Transformers.
She most recently appears on the hit comedy television series, New Girl. Although, these days, it seems that she has particularly slowed down on her television and film appearances.
Emmanuelle Vaugier as Mia | Then
Emmanuelle Vaugier played the character named Mia, a dance teacher who supposedly had no interest in Charlie. It was only up until Charlie announced that he had a nephew, Jake, who really enjoyed dancing, that Mia gave a chance to him. Much to his dismay, Mia had pretty harsh demands, forcing him to give up eating meat, smoking, drinking, and the worst of them all - having sex. Charlie deceives her into agreeing to do all of these things, secretly continuing them behind her back.
Ultimately, the two almost get married but Mia decides to end it after Charlie discloses that there isn’t any chance that his brother would move out of his beach house.
Emmanuelle Vaugier as Mia | Now
Canadian actress, singer, and model, Emmanuelle Vaugier, continued on to nail several acting jobs after her appearance on the show. From appearing in television shows like Lost Girl and Mistresses, Vaugier continues to work hard in having her career bloom.
She recently starred in a television movie, Killer Ending, and is set to appear in My Mother’s Stalker, Masks Don’t Lie, and Don’t Look There.
Marin Hinkle as Judith Harper-Melnick | Then
Judith was Alan’s first wife, daughter of Lenore and Sheldon, and the biological mother of Jake Harper and Milly Melnick. Their marriage turned out to be so cold that she mentions that the only time she ever felt happy being sexual was when she was pregnant with Jake. Ouch!
Later on in the series, they eventually end their marriage and Judith moves on to remarrying Dr. Herb Melnick, Jake’s pediatrician.
Marin Hinkle as Judith Harper-Melnick | Now
Marin Hinkle, now 51 years old, still continues to develop her acting career. Aside from appearing in the dramatic series, Madam Secretary, on CBS, she also appeared on the shows, Speechless and Homeland. She continues on headstrong into her craft as she just wrapped up a movie called Before/During/After.
Just as her career is successful, her marriage with Randall Sommer is as well.
Allison Janney as Beverly | Then
Beverly was the woman that Alan met on a dating network. In hopes of impressing her, Alan tricks her into thinking that the beach house was solely his. But after feeling bad about her issues of divorce, Alan eventually admits that the house is actually Charlie’s.
Luckily for Alan, Beverly understands as she had problems way worse than he did. Well, it turns out that her demons were way bigger than he expected. Charlie walked in on Alan and found him tied up to his bed! Freaky!
Allison Janney as Beverly | Now
We’re pretty sure you recognize Allison Janney from one of her television or movie appearances. She’s actually a highly prolific character actress who is revered for her versatility. She has appeared on hit films like Hairspray, Juno, and The Girl on the Train. Yup, that’s probably why she looks familiar to you!
Her work on screen, stage and television have received the acclaim that brought her numerous accolades, including seven Primetime Emmy Awards, an Academy Award, a BAFTA Award, and a Golden Globe Award, just to name a few. Impressive!
Brooke Shields as Danielle Stewart | Then
Danielle was the girl with a partying past. This didn’t seem to stop Charlie from setting her up with Alan. She ended up dating him, believing he would change for her, something she did not receive from her other boyfriends.
However, when she mentions to Charlie, “I’ve slept with a lot of guys and even a few women and even with couples”, he suddenly decides he wants to be with Danielle now. The brothers end up fighting over her, causing her to leave.
Brooke Shields as Danielle Stewart | Now
Brooke Shields was already a recognized actress and model before she had appeared on the show. Already receiving a lead role at the young age of 12, Brooke had continued on to book major roles in shows and films such as The Blue Lagoon, Endless Love, and a recurring role in NBC’s Law & Order: Special Victims Unit.
She also received two Golden Globe nominations for her performance on the NBC sitcom, Suddenly Susan.
Jeri Ryan as Sherri | Then
Though Charlie had seemed to have gone through all kinds of women, Sherri was the kind of girl he never encountered before. She was a woman skilled at playing hard to get, constantly leading Charlie on into having sex with her.
But 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 | Now
Jeri Ryan is a German-born American actress who is best known for her role on Star Trek: Voyager, for which she earned and won four nominations for a Saturn Award. She is also known for her performances on several television series such as Boston Public, Dark Skies, and Shark.
The talented actress is currently in the works for her next film, The Relic.
Kimberly Williams-Paisley as Gretchen Martin | Then
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 the show’s 11th season, keeping a relationship with who she thought was “Jeff Strongman”. This, apparently, was Alan’s alter-ego, an identity that Alan gets very into.
Eventually, Gretchen deciphered his lies and breaks up with him, telling him she already experienced all this dishonesty with her ex-husband.
Kimberly Williams-Paisley as Gretchen Martin | Now
Kimberly Williams-Paisley is best known for her co-starring roles on Nashville and According to Jim. Though she seemed to have slowed down on her acting after the show, she still made guest appearances on television shows, including Tales From The Crypt, George Lopez, and Less Than Perfect.
Her latest project is a film made for the winter season, The Christmas Train. Paisley is probably focusing more on her happy marriage to Brad Paisley.
Judy Greer as Bridget Schmidt | Then
As we are introduced to Ashton Kutcher’s character, it is revealed that he was deeply heartbroken from his divorce with his ex-wife, Bridget. He, apparently, loved her so deeply that he was even willing to take his own life, knowing she didn’t want to take him back.
Though she initially refuses to reconcile with him due to his immaturity, she somehow changes her mind when she finds out he started dating another girl. She then comes to the beach house begging for him to take her back, to which Walden responds with a finalization of their divorce. Ouch!
Judy Greer as Bridget Schmidt | Now
You’ve probably seen Judy Greer in many shows and films already as the actress 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.
She’s also well-respected for her voiceover work in animated shows such as StoryBots and Archer. Judy’s most recent and popular work can be seen in the hit films, Ant-Man and the Wasp, Halloween, and Driven.
Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Then
Zoey was known as the gorgeous British ex-girlfriend that Walden got really serious with after his divorce with Bridget. After dating for two seasons, Zoey actually could have been Walden’s fiancée, if it were not for her rejection of his marriage proposal. Walden then discovers that Zoey had been dating another man behind her back and decides to seek revenge.
He ended up leaving her daughter Zoey a ferocious and violent dog for her birthday in hopes of getting back at Zoey and her new lover. That’s some straight up bitterness right there!
Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Now
Something particularly surprising about this British beauty is that she is actually considered royalty! Sophie Winkleman is the wife of Lord Frederick Windsor, son of Prince Michael of Kent, Queen Elizabeth II’s first cousin. As such, she’s actually known as Lady Frederick Windsor.
The English actress, though basking in royalty, still went on into her acting career, voicing a character on the show Milo Murphy’s Law. She’s also currently filming a new show called Trust, featuring Donald Sutherland and Hilary Swank.
Melanie Lynskey as Rose | Then
Rose became one of the main characters of the show, and one of the crowd’s favorites as well! What Charlie thought would be a one night stand, developed into an obsession in which Rose becomes his stalker, only living a few houses down.
Later on in the show, Charlie somehow eventually falls for her and the two decide to get engage and run off to Paris together. Unfortunately, Charlie’s character dies before they are able to tie the knot.
Melanie Lynskey as Rose | Now
Melanie Jayne Lynskey is a New Zealand actress known for her portrayals of being the soft-spoken, quirky, and flawed character. She went on to gain numerous awards for the acting opportunities she received after the show. These awards included a New Zealand Film Award, a Hollywood Film Award, and a Sundance Special Jury Award, to name a few. She also received critical acclaim for her leading role in Hello I Must Be Going, proving to be the turning point in her career.
She recently starred in films such as Happy Christmas, The Intervention, I Don’t Feel At Home In This World Anymore, and Sadie.
Ming-Na Wen as Linda Harris | Then
Linda Harris was a judge whom Charlie dated for a brief period of time. She first met Charlie after Alan planned a double date involving his brother. Although Charlie was really fond of her, Linda actually found him repulsive for his lecherous nature.
The entertainment ensued when Charlie was caught drunk driving and ended up in court, embarrassed to see Linda as the judge. After some time, Linda decides to end it after Charlie embarrasses her at her awarding ceremony.
Ming-Na Wen as Linda Harris | Now
Ming-Na-Wen was actually famously known for being the voice of the Disney character Mulan. She’s also probably recognizable to you as she played the role of Melinda May in the ABC action drama series, Agents of S.H.I.E.L.D., as well as the role of Dr. Jing-Mei Chen on the medical drama series ER.
Besides television, Ming is also notable for starring in films such as Street Fighter, The Joy Luck Club, and Final Fantasy: The Spirits Within.
Heather Locklear as Laura | Then
As Alan and Judy were going through their divorce settlement, Charlie screwed up their relationship by sleeping 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.
Alan ended up letting her go and hired a new lawyer instead.
Heather Locklear as Laura | Now
Heather Locklear was already an accomplished television actress before she made an appearance on the show. She was most notable for her roles on Spin City and Melrose Place. Though she’s gained recognition as an actress, Locklear still had her fair share of public drama and controversy.
She went through a very publicized divorce and went through numerous health issues. Fortunately, she was able to get her life back on track and has gotten back to her acting work, appearing in shows like Franklin & Bash and Tyler Perry’s Too Close To Home.
Gail O’Grady as Mandi | Then
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. They even continued their sexual frenzy later on that day at Judith’s house in the hot tub.
Apparently, Kandi and Mandi looked so alike that strangers mistook them for sisters.
Gail O’Grady as Mandi | Now
Gail Ann O’Grady is an actress and producer, best known for her appearances on television. She went on to booking lead roles in a number of television movies and her career ended up going so well that she was even nominated for a Primetime Emmy Award three times.
Her personal life, though, is another story. Gail went through 6 marriages, with all of them failing. Though, she still seems to believe in love as she is currently dating Chris Beyers.
Paula Marshall as Paula | Then
After meeting at a nightclub, Paula and Alan really seemed to hit it off. Paula eventually felt comfortable enough to reveal that she was actually once a man named Paul. Fortunately for her, Alan didn’t seem bothered by it and continued on to a relationship with her.
It all ends up getting weird and messy when Paula tells Alan that she wants to be in an open relationship after he meets her ex-wife Rachel. Alan then sees the two kissing each other, eventually ending up with them trying at their relationship again. Poor Alan!
Paula Marshall as Paula | Now
Paula Marshall continues to thrive in her acting career, appearing in hit shows like 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!”.
Married to one of the Titanic stars, Danny Nucci, Marshall and her husband have also been raising their only daughter Maya.
Missi Pyle as Miss Pasternak | Then
Charlie, apparently, didn’t have any kind of limit when it came to women. Not even for his elementary school teacher! Miss Pasternak was Charlie’s fifth-grade teacher who suspended Jake for giving her the finger. The two shockingly began dating, with Miss Pasternak lifting his suspension and even giving him good grades without rightfully earning them!
When Charlie realized that she was mentally ill though, he ended up dumping her.
Missi Pyle as Miss Pasternak | Now
Andrea Kay Pyle, or more popularly known as Missi Pyle, is an actress and singer has appeared in several films, including some award-winning films such as The Artist, Big Fish, 50 First Dates, Charlie and the Chocolate Factory, and Gone Girl. Yup, absolute blockbusters!
The actress maintaining her successful career, working on many projects that are currently in the post-production process. We’ll surely be seeing her frequently on the big screen!
Kimberly Quinn as Donna | Then
Donna was Alan’s ex-girlfriend who was dumped due to Alan’s boredom. Donna first met Alan in a blind date, hitting it off pretty well. hysterical after he breaks it off.
It wasn’t long until Alan started to get tired of her company. Not wanting to hurt her feelings, Alan asks advice from Charlie on how to not dump Donna harshly. Unfortunately, Charlie’s advice didn’t suffice, leaving Donna completely Kimberly
Quinn as Donna | Now
Kimberly Quinn is an all-around powerhouse, engaging in acting, writing, producing, directing, and co-founding films with her husband, writer-director, Theodore Melfi. She has proved to be as much of a force behind the camera as she is in front of it.
The talented starlet can soon be seen starring opposite Vincent D’Onofrio, Dax Shepard, Jessica Alba, and Tim Allen in her next feature film, “El Camino Christmas”.
Justine Eyre as Gabrielle | Then
Gabrielle was Charlie’s girlfriend up until Alan decided to steal her. Apparently, Alan was seeking revenge after finding out that it was Charlie who stole his high school lover from him. Charlie obviously reacts badly, expressing that he felt betrayed by his own brother. In regret, Alan apologizes and says he will give her back, but Charlie thinks it’s too late.
Though the two keep seeing each other, Alan eventually feels uncomfortable and goes home. Upon coming home, he sees Charlie with Charity who deviously tells Alan, “now we’re even”. Burn!
Justine Eyre as Gabrielle | Now
The stunning Canadian actress and model, Justin Eyre, has made a few more television appearances after the show. Though her career hasn’t blown up as big as most of the stars on this list, she was still able to nail roles on hit shows like Mad Men, The Secret Life of the American Teenager, and CSI: Miami.
She’s recently taken a break from acting but hopefully decides to return soon.
Maggie Lawson as Ms. McMartin | Then
Ms. McMartin was the assigned social worker when Alan and Walden decided to adopt a child. Impressed with their lifestyle, Ms. McMartin provides them with a 6-year-old African-American boy named Louis. However, when she realizes that the “couple” has deceived her, she instructs Louis to be removed from the house. In an attempt to change her mind, Alan ends up sleeping with her.
The two eventually begin a relationship until she leaves him for Walden. Nope, not messed up at all!
Maggie Lawson as Ms. McMartin | Now
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.
The actress also played the role of Juliet O’Hara in the movie version of Psych.
Denise Richards as Lisa | Then
Played by Denise Richards, Lisa was one of Charlie’s love interests in season 1. She and Charlie had lived together in Charlie’s beach house up until he realized he was not willing to be in a committed relationship.
After the two break up, Lisa discloses to Charlie that she plans to get married. Struck by jealousy and regret, Charlie tries winning her back by pretending he has changed into a family-oriented man. Lisa ends up divorcing her husband for Charlie but is once again dumped because of his fear of commitment.
Denise Richards as Lisa | Now
Denise Richards is definitely a unique addition to this list as she was actually married to Charlie Sheen in real life! The two were married for 4 years, raising their two daughters Lola and Sam.
Though their marriage ended, Richards’ television success certainly did not. After appearing in numerous hit films, Richards starred in the E! reality show, Denise Richards: It’s Complicated. She then became a series regular on the comedy sitcom Blue Mountain State and currently stars in the reality show, The Real Housewives of Beverly Hills.
Conchata Ferrell as Berta | Then
Playing as the cynical, sharp-tongued, sassy, hard-working character is Berta, the housekeeper. Though she was probably the only woman in the show that Charlie didn’t develop feelings for, she still offered loads of comic relief for the audience.
Berta takes great satisfaction in making fun of the Harper family for all their unfortunate twists and turns as they amuse her. She is definitely considered a fan favorite!
Conchata Ferrell as Berta | Now
Conchata Ferrell is well known for her character work, receiving two Primetime Emmy Award nominations for her exceptional performances. The American actress has still been active in the industry, even nailing a role as Shirley on the Netflix comedy show, The Ranch.
She was also most recently featured in the film, Deported. But no matter the role given to Ferrell, people will always know and love her for playing Berta!
Jenny McCarthy as Courtney Leopold | Then
Courtney Leopold was the minor recurring character in the show. She was played as the former professional con-artist, and eventually Charlie’s temporary girlfriend. Though Alan warns Charlie of Courtney’s sociopathic tendencies, he still decides to go on with their relationship. Alan is, of course, proven right after Courtney successfully convinces Charlie to give her $50,000 and give her a Ferrari. Talk about lavish needs!
Charlie then proposes to her but ends up not pushing through with the marriage after finding out that her real name is Sylvia and her parents are con-artists in reality. That’s some pretty sketchy stuff right there.
Jenny McCarthy as Courtney Leopold | Now
Jenny McCarthy, sometimes credited as Jenny Wahlberg, is an actress, activist, model, television host, author, and screenwriter. The bombshell was actually very well known for being a nude model for Playboy magazine way before she appeared on the show. She even won Playmate Of The Year!
She went on to appear in shows and films, including Diamonds, Scream 3, and Santa Baby. She’s also known for her publicly announcing her controversial views on the ABC talk show, The View.
Teri Hatcher as Liz | Then
Liz is Judith’s sister and is seen as the “sleaze-ball” in the show. She is the woman Charlie ended up having sex with in the coatroom during Alan and Judith’s wedding, though he does not remember. She is introduced for the first time at Jake’s birthday party which eventually gets messy. Judith and Liz get into some heat after Judith sees Liz hitting on Alan.
In a comical twist, Liz ends up taking Alan to a room and Judith grabs Charlie along with her instead. However, both sisters just end up backing out.
Teri Hatcher as Liz | Now
After appearing on the show, Teri Hatcher went on to make it big in Hollywood. She starred as Susan Mayer on the hit drama series, Desperate Housewives.
Working on the show for eight tedious years, Teri ended up winning the Golden Globe Award for Best Actress in a Musical or Comedy, a Primetime Emmy nomination for Outstanding Lead Actress in a Comedy Series, and three Screen Actors Guild Awards!
Jaime Pressly as Tammy | Then
Tammy is the ex-girlfriend of Jake Harper and also the mother of three children. Although all her tattoos may say otherwise, Tammy is actually a soft and good-hearted woman.
It’s no wonder she felt absolutely torn and betrayed when she found out that Jake had sex with Tammy’s daughter, Ashley. That indeed was a little too far!
Jaime Pressly as Tammy | Now
Jaime Pressly went on to achieve remarkable success in her career after appearing on the show. She was actually best known for her role as Lola Sombrero in The Oogieloves in the Big Balloon Adventure, bagging two Emmy Award nominations, as well as a Golden Globe Award and a Screen Actors Guild Award!
She then appeared in hit films such as Not Another Teen Movie, DOA: Dead or Alive, and I Love You, Man.
Krista Allen as Olivia Pearson | Then
Though she was already a girlfriend of Charlie in the past, Olivia was formally introduced into the show when Charlie, Alan, and Jake Harper visited their mother at a dinner.
Everything turns out to be a wreck when Olivia and Charlie start talking about their failed relationship. The heated discussion involved Olivia throwing her drink in Charlie’s face, ending the dinner prematurely.
Krista Allen as Olivia Pearson | Now
Krista Allen is a comedian and actress, moving on to being renowned for her appearances in the television series, Days of Our Lives and Baywatch. She’s also recognizable for her appearances on the big screen in Hollywood blockbusters such as The Final Destinations and Anger Management.
In addition to her career in acting, Allen also spends her time headlining across Los Angeles as a stand-up comedian.
Kristin Dattilo as Cindy | Then
Cindy was one of the characters that stood out for not getting into bed with Charlie. For a guy that can easily urge any woman to have sex with him, Charlie certainly did not take Cindy’s rejection well.
She ended up being Jake’s first “crush” and ends up being on one of his erotic drawings.
Kristin Dattilo as Cindy | Now
Kristin Dattilo went on to establish her career, landing her distinguishable role as Yola Gaylen on The Chris Isaak Show. She also appeared on hit shows like CSI: Crime Scene Investigation, Dexter, Beverly Hills, 90210, Friends, and Veronica Mars.
After taking some time off to take care of her two children, Dattilo is now developing multiple projects in the industry.
Liz Vassey as Kate McLaughlin | Then
Kate is the nice, single mother who was introduced to Charlie at Jake’s soccer game. Upon meeting him, Kate finds it hilarious that Charlie appeared to look wasted and eventually starts hitting it off with conversations.
She made another appearance on the show but as Charlie’s dermatologist, Michelle. The scene ends up being absolutely priceless when she is seen removing a mole off of Charlie’s behind. The two begin to date until Michelle finds out about Charlie’s other woman.
Liz Vassey as Kate McLaughlin | Now
It was probably peculiar for Liz Vassey to be cast twice as different characters but who’s complaining?
Since her appearance on the show, Vassey continued to work on others show such as the web series, Nikki & Nora. Though, the actress is best known for her role as Wendy Simms in CSI: Crime Investigation, a role she played for five years straight!
Paget Brewster as Jamie Eckleberry | Then
Growing up, Alan and Charlie always knew Jamie Eckleberry as the chubby and unattractive kid whom they harshly nicknamed, “Eckleberry hound”. The two obviously become shocked when they see that Jamie grew up to be absolutely gorgeous.
They end up trying to hit on her but she rejects both of them. She definitely gave them a taste of their own medicine!
Pagent Brewster as Jamie Eckleberry | Now
Though this was after her appearance on the show, Pagent Brewster was actually first recognized for her role as Kathy on the popular sitcom, Friends. She then made her career breakthrough as Special Agent Emily Prentiss on the CBS crime drama Criminal Minds, appearing regularly from 2006 to 2012.
Though she’s appeared mostly on television shows, her most recent work was done for a horror film, The Witch Files.
Rachel Cannon as Chloe | Then
After dating Charlie for a little while, Chloe ended up getting dumped for being way too clingy. It was only up until Chloe fell for Charlie’s handyman, that he starts decided to win her back. Out of jealousy, he makes the effort of showing up to the handyman’s house all dressed up in trendy clothes.
In the end, though, he fires Fernando and lets him stay with Chloe.
Rachel Cannon as Chloe | Now
We’re pretty sure some of you may recognize Rachel Cannon’s face. After the show, the American actress became widely known for her roles on Mad Men, The Big Bang Theory, and Fresh Off The Boat!
Though she’s moved on to much bigger roles than those of her past, we’re hoping to see her get cast for a leading role in the near future.
Sara Rue as Naomi | Then
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”. Such harsh words stem from the fact that Naomi ended up getting pregnant and losing her job, forcing her to move in with her mother for the financial and emotional support. She is introduced to the Harper brothers and develops a crush on Alan whom she, later on, conceals from her mother.
Berta eventually discovers that the two have been dating but surprisingly approves of it. Unfortunately, Naomi leaves Alan when her child’s father returns.
Sara Rue as Naomi | Now
Sara Rue took on many career opportunities after the show and became best known for her performances on the series, Popular and Less than Perfect. She even hosted the reality series Shedding for the Wedding in 2011!
She also landed a number of roles on other television shows, including The Big Bang Theory, Eastwick, and Rules of Engagement. You can catch her most recent work on the popular Netflix show, A Series of Unfortunate Events.
Miley Cyrus as Missi | Then
On his weekend leave from the Army, Jake meets Missi and quickly falls in love with her, making her one of his first sexual partners ever. The show reveals early on that though Missi is particularly talkative and odd, she is much smarter and kinder than most of the girls on this list.
Missi and Jake move on to planning to enjoy a romantic night when suddenly, Alan finds out that Jake has gone AWOL. Missi then decides that letting her go would be best and tells Jake to go back to base.
Miley Cyrus as Missi | Now
We probably don’t need to brief you on who exactly Miley Cyrus is anymore. Obviously, she’s one of the most famous celebrities to ever appear on the show! She was already incredibly established as an actress and singer way before the show as the star of her own Disney show, Hannah Montana.
Thus, her fans that regularly tune in truly enjoyed the feature. Though she’s done a significant amount of acting work, Miley continues on to climb up on her singing career. She even just released her latest album, Younger Now.