Take A Look At The Lives Of The Female Cast Of Two And A Half Men

Published on 10/29/2020
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Airing its pilot episode on September 23 of 2003, the American comedy sitcom named “Two and a Half Men” ran for a total of 12 seasons, with its final episode being on February 19, 2015. The show was a total success and gained a lot of viewers. It was first aired on the television broadcasting company named “CBS” and later partnering with Warner Bros Television for the production. The sitcom is about a lot of things such as dating, love, divorce, parenthood, friendship, singleness, men, women, and money. The show featured a lot of beautiful ladies throughout its runtime. Keep reading to find out how the ladies of the show are doing right now!

Missi Pyle As Miss Pasternak Then

It seemed at the beginning that Miss Pasternak and Charlie would make a good couple. Jake’s relationship even helps bring up his grades! But all things that are good come to an end. We find out later on that she is banned from the teaching profession. What makes the situation worse is that, instead, she begins to dance to make a living.

Missi Pyle As Miss Pasternak Then

Missi Pyle As Miss Pasternak Then

Missi Pyle As Miss Pasternak Now

Missi Pyle has taken on different projects on both the big screen and the small screen over the years. She’s Earl, Mad About You, Mom, Two Broke Girls, and Friends in My Name. It’s awesome to hear that she’s musically talented, too. She is even a member of Smith & Pyle, a country-rock duo. She’s now married and divorced twice.

Missi Pyle As Miss Pasternak Now

Missi Pyle As Miss Pasternak Now

Marin Hinkle As Judith Harper-Melnick Then

Marin Hinkle, as the woman who brought Judy to life, was a pillar of the show. Her character is Alan ‘s ex-wife and the mother of Jake. Even if they agree to be their son’s co-parent, they usually fight for money. Alan likes to call her out on her spending habits and love for cosmetic surgery and luxury items. When Judith falls in love with Jake’s doctor and marries him, it gets worse. Ultimately, she learns that he’s cheating and divorcing her.

Marin Hinkle As Judith Harper Melnick Then

Marin Hinkle As Judith Harper-Melnick Then

Marin Hinkle As Judith Harper-Melnick Now

Marin Hinkle got acting projects left and right once the show was over. For her time on the show, Madame Secretary fans need to know her. Besides this, she was in Speechless and Homeland, too. As for her large-screen projects, Before / During / After would be one of the most recent ones. In Two and a Half Men, she was considered to be something of a psycho ex, but this can not be further from the truth. She has been married to Randall Sommer since.

Marin Hinkle As Judith Harper Melnick Now

Marin Hinkle As Judith Harper-Melnick Now

Emmanuelle Vaugier As Mia Then

It’s important to know that Charlie enjoys chasing women! Until his mission is complete, he refuses to give up. This is what happened when Mia, a dance teacher, met him. He even asks Jake to learn to dance in order to get closer to her. Not only that, but he agrees to be able to go out with her when she asks him to quit meat, drinking , and smoking. Charlie promises her to do these things, but she hesitates to do them anyway. Unfortunately , things end when she learns the truth.

Emmanuelle Vaugier As Mia Then

Emmanuelle Vaugier As Mia Then

Emmanuelle Vaugier As Mia Now

When she was done with the show, what did Emmanuelle Vaugier get up to? Well, she continued to appear in Mistresses, Rogue, One Tree Hill, and Lost Girl on the small screen. When you watch more movies than shows, you may recognize her from Washed Away, Destruction Los Angeles, and Masks Don’t Lie. It’s pretty neat that she was also on the Maxim “Hot 100 List.” The last one is a thriller film set in Italy’s Venice.

Emmanuelle Vaugier As Mia Now

Emmanuelle Vaugier As Mia Now

Holland Taylor As Evelyn Harper Then

Women tend to flit in and out of their lives, but their mom has never escaped from Charlie and Alan. Holland Taylor played to perfection with their mother! She is the only person in the TV show who could give them a piece of her mind, even though the lead characters had a messy relationship with her. She also has a reputation as a gold-digging woman interested only in older men. Alan and Charlie were much less fond of her, even though she was a hit among the viewers.

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Holland Taylor As Evelyn Harper Then

Holland Taylor As Evelyn Harper Now

Holland Taylor is already a pretty big star in her own right, even if she didn’t appear on the show. In fact, since the ’80s, she has been making waves! In the role of Evelyn Harper, she has snagged four nominations for the Best Supporting Actress award over the years. Apart from Two and a Half Men, she was also with Mr. Mercedes and Legally Blonde.

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Holland Taylor As Evelyn Harper Now

Melanie Lynskey As Rose Then

Rose is introduced on the TV show as someone who, after one night together, develops an obsession with Charlie. She shrugs off the rejection and still stalks him. When she finally gets lucky, a lot of viewers can’t help but be shocked. Charlie agrees to marry her, and they run off to Paris , France, eventually. Unfortunately, because he ends up dying before they can exchange their vows, things do not work out.

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Melanie Lynskey As Rose Then

Melanie Lynskey As Rose Now

Melanie Lynskey isn’t lovely? In the past, the brunette was in films such as Heavenly Creatures, Coyote Ugly, and Sweet Home Alabama. In projects such as Happy Christmas, I Don’t Feel at Home in This World Anymore, The Intervention, and Hello I Must Be Going, she only earned leading roles later. She and Jimmi Simpson once called each other man and wife for seven years, but she is now engaged to Jason Ritter.

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Melanie Lynskey As Rose Now

Jennifer Taylor As Chelsea Melini Then

Do you remember Two and a Half Men’s Chelsea Melini? As the first female character to whom Charlie confesses, most fans of the show think that she is remarkable. When, for the first time, he wears his heart on his sleeves, she eventually tires him. This makes her leave him for a layer of Alan’s. Ouch. Ouch.

Jennifer Taylor As Chelsea Melini Then

Jennifer Taylor As Chelsea Melini Then

Jennifer Taylor As Chelsea Melini Now

One thing about the role of Jennifer Taylor in the show is that she wasn’t even meant to be around for a long time. She appeared for six seasons on the show, but it wasn’t supposed to be this way. For reasons that we are unsure of, the producers decided to keep her character. Jennifer also had a good career and, after her role in the sitcom, appeared in numerous TV shows and movies. She is married to Paul Taylor at the moment and has 2 children with him.

Jennifer Taylor As Chelsea Melini Now

Jennifer Taylor As Chelsea Melini Now

Allison Janney As Beverly Then

With the help of a dating site, Alan meets Beverly. He does not tell her the truth about the house, however. He even tells her that to impress her, he’s the owner. He feels guilty about his dishonesty as she finally talks about her exes. He breathes a sigh of relief once he tells her the truth, because she does not seem to mind. For a while, they’re together until his brother finds her tying him up.

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Allison Janney As Beverly Then

Allison Janney As Beverly Now

Allison Janney had already made a name for herself in the industry prior to her appearance in Two and a Half Men. From 1999 to 2006, she was in The West Wing, for one thing. She has appeared in movies like Juno, Hair Spray, and The Girl on the Train, aside from that. Nowadays, on a TV show called Mom, she plays Anna Faris’ mom.

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Allison Janney As Beverly Now

Jeri Ryan As Sherri Then

Charlie is convinced, with the introduction of Sherri, that he has finally met the one for him. He likes that in the beginning, she does not fall for his tricks. Even at first, he finds it attractive! He ends up getting tired of the fact, unfortunately, that she is always one step ahead of him. She first tries to get with Alan to no avail once the two of them finally break up.

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Jeri Ryan As Sherri Then

Jeri Ryan As Sherri Now

Jeri Ryan’s career after her work in the comedy sitcom was at its height at that time. The American actress first caught the attention of the people thanks to her role in “Borg Drone Seven of Nine” in the film Star Trek: Voyager. She was formerly married to actor Jack Ryan but had to split due to conflicting schedules. She currently has two kids with her current husband Christophe Eme.

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Jeri Ryan As Sherri Now

Kimberly Williams-Paisley As Gretchen Martin Then

Alan ends up dating Gretchen, the sister of Larry Martin. But even with her, he is not truthful. He claims that the apartment is his property, but the lies continue to grow and grow. Ultimately, he can’t keep track of everything he tells her anymore. She breaks it off once she learns that he has lied to him. She also says she used to be married to a liar who is pathological and refuses to go through the same thing again.

Kimberly Williams Paisley As Gretchen Martin Then

Kimberly Williams-Paisley As Gretchen Martin Then

Kimberly Williams-Paisley As Gretchen Martin Now

Kimberly started acting at an early age, so it would not come off as a surprise if you recognize before she joined the cast of Two and A Half Men. She was well known for her role in Father of the Bride and she is also known to have spent eight years on the show According to Jim. She also worked on movies such as The Christmas Train, and Darrow and Darrow. Kimberly married renowned country singer-songwriter Brad Paisley in 2003, and later renewing their vows in 2015.

Kimberly Williams Paisley As Gretchen Martin Now

Kimberly Williams-Paisley As Gretchen Martin Now

Ming-Na Wen As Linda Harris Then

Alan and Charlie are going for a double date, and this is how Linda meets the latter. He feels drawn to her in no time at all. She doesn’t, however, fall for him like every other woman in the show right away. Until he gets a DUI, she turns down his advances. He is surprised to see that, in his case, she is the judge. Even though she gives him a chance after that, not very long after that, their romance ends.

Ming Na Wen As Linda Harris Then

Ming-Na Wen As Linda Harris Then

Ming-Na Wen As Linda Harris Now

Unlike the other ladies in the list, Ming-Na Wen is not as popular as the other ladies due to her preference to be a non-Hollywood actress. She is best known for her role in the animated musical historical action adventure Disney film Mulan as the speaking voice for the main character “Fa Mulan” and aside from her work in Mulan, she also voice acted for other animated films such as Sofia the First and Ralph Breaks the Internet: Wreck-it Ralph 2 etc.

Ming Na Wen As Linda Harris Now

Ming-Na Wen As Linda Harris Now

Gail O’Grady As Mandi Then

Gail O’Grady plays the character of Mandi, the mother of Kandi. In case you have not seen the show, Charlie has a reputation for obsessing over women and goes for every woman he comes across every time. Like literally, he would go for it every time he can. Because of that, it is not much of a surprise that Charlie went for Mandi. However, Alan was not comfortable with the idea of Charlie being close with his mother-in-law. Mandi was only looking at Charlie’s house for her daughter, Kandi.

Gail O’Grady As Mandi Then

Gail O’Grady As Mandi Then

Gail O’Grady As Mandi Now

Gail O’Grady played a lot of other roles after her work in the sitcom. The actress also appeared in shows like American Dreams, Ms. Fields, and Revenge, with her roles in the said series being virtually the same. The actress has been married six times in the past, with her claiming that one of her former lovers was stalking her and tried to put him on restraining order (which wasn’t granted). He latest relationship was with John Stamatakis, which ended in 2008.

Gail O’Grady As Mandi Now

Gail O’Grady As Mandi Now

Paula Marshall As Paula Then

We all know that in terms of dating, Alan is not the most fortunate guy. He thinks his luck has finally turned around when he meets Paula at a nightclub. Things get complicated when she tells him that she used to be called Paul and is married. She tells him that she is looking for an open relationship and also tells her wife to date him. Needless to say, in the end, their plan didn’t really work out.

Paula Marshall As Paula Then

Paula Marshall As Paula Then

Paula Marshall As Paula Now

Paula Marshall’s first TV appearance was not in the comedy sitcom Two and A Half Men, but on a guest appearance she made with a young Clark Kent on Superboy in 1991. She also appeared in other films such as Murder in the First, and The Mentalist. Other notable works of her include We Love You, Sally Carmichael. She currently has a child and is happily married to Danny Nucci who played the role of Fabrizio in the movie Titanic.

Paula Marshall As Paula Now

Paula Marshall As Paula Now

Tammy Lauren As Shannon Then

When Judith and Herb get married for the second time, Shannon is introduced in the show. Alan discovers that she and Herb used to be involved! This ensures that at the moment they both still have to move on from their exes. The whole time, they try to make the bride and groom jealous, but Shannon takes it too far in the middle of the ceremony by screaming Alan ‘s name. They’re failing to win back any of their exes.

Tammy Lauren As Shannon Then

Tammy Lauren As Shannon Then

Tammy Lauren As Shannon Now

Tammy Lauren’s character of Shannon is the first woman we have on the list that did not have any romantic connection with the two brothers. Her career did not progress as fast even after her work in the sitcom Two and A Half Men. Unlike the other ladies in this list, she did not experience a lot of time in the limelight. She is well known for starring in the 1997 horror film Wishmaster, portraying Alexandra Amberson The actress married Israeli actor, Guri Weinberg in 1997.

Tammy Lauren As Shannon Now

Tammy Lauren As Shannon Now

Justine Eyre As Gabrielle Then

Was there a particular point in the show where there was no drama at all? When Charlie begins dating Gabrielle, Alan learns that his brother stole his high school girlfriend. He tries to steal Gabrielle in order to get revenge, but can’t go through with it because it makes him uncomfortable even though it works. He sees his brother hooking up with his high school girlfriend again when he returns home!

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Justine Eyre As Gabrielle Then

Justine Eyre As Gabrielle Now

Much like Tammy Lauren in the list, Justine Eyre’s appearance in the sitcom did not put her in the limelight like the other female characters in the show. Offers for various show barely came for her thus making it difficult to help her career grow. Despite that, Justine managed to land roles in projects such as Mad Men, American Teenager’s Secret and CSI: Miami. Despite her unlucky career, she is happily married to screenwriter John Allen Nelson.

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Justine Eyre As Gabrielle Now

Maggie Lawson As Ms. McMartin Then

Charlie might be killed off, but when it comes to the ladies, Alan, Walden, and Jake pick up where he left off. As they fall in love with Ms. McMartin, Alan and Walden are thinking of adoption. The social worker assigns Louis to them, but realizes that the application was not honest. She forgives them and begins to date Alan. She soon changes her mind and instead goes after Walden.

Maggie Lawson As Ms. McMartin Then

Maggie Lawson As Ms. McMartin Then

Maggie Lawson As Ms. McMartin Now

The American actress Maggie Lawson is known to have an amazing career before she showed up in Two and a Half Men. After her show, her career progressed even further. She can be seen in various projects such as Great Outdoors, Psych, and Angel from Hell. She also plays a role in the 2017 adaption of the film Psych as Juliet O’Hara. She also had a recurring role as Nathalie Flynn on Fox’s Lethal Weapon in 2019. She was married to Ben Koldyke but they separated in 2017.

Maggie Lawson As Ms. McMartin Now

Maggie Lawson As Ms. McMartin Now

Conchata Ferrell As Berta Then

The only other female character who is a regular on the show is probably Berta. Due to her sharp tongue and cynical outlook of life, she usually gets into fights with Charlie. She is another mother figure in the show, at any rate. The fans loved her, so even after Charlie Sheen left the project, the producers kept her on the show. Did you know that Berta appeared in all the show’s seasons?

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Conchata Ferrell As Berta Then

Conchata Ferrell As Berta Now

We will never forget the contribution of the talented Conchata Ferrell to the series. She was nominated twice for the Outstanding Supporting Actress in a Comedy Series award at the Primetime Emmys. As part of the original cast of Lanford Wilson’s The Hot l Baltimore, she is also known to have been a member of Broadway and won the Drama Desk, Obie and Theatre World Best Actress Awards for her performance in the off-Broadway play The Sea Horse. She later reunited in the TV show called The Ranch with fellow Two and a Half Men cast by Ashton Kutcher.

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Conchata Ferrell As Berta Now

Jenny McCarthy As Courtney Leopold Then

In the show, Charlie continues to date Courtney Leopold even though his mom is marrying her dad. Alan can tell that the whole situation has something iffy about it and warns him about it. He refuses to give her up, even when Courtney gets Charlie to give her a Ferrari and $50,000. The truth comes out in the end. She is, apparently, actually a con artist! Her dad is also nothing more than an actor.

Jenny McCarthy As Courtney Leopold Then

Jenny McCarthy As Courtney Leopold Then

Jenny McCarthy As Courtney Leopold Now

The truth is that even before she was in Two and a Half Men, Jenny McCarthy was already making it big. The host and Playboy bunny of this MTV dating show had a self-titled show of their own. She was also married to Jim Carrey once, but in 2010, they split up. She and Donnie Wahlberg are married happily these days. They actually even appeared together on a reality TV show. She has worked as a writer and activist as well.

Jenny McCarthy As Courtney Leopold Now

Jenny McCarthy As Courtney Leopold Now

Teri Hatcher As Liz Then

Alan and Judith have a complex relationship with each other, but with her sister’s arrival, things only get worse. At their wedding, Liz and Charlie hooked up, but he couldn’t remember that this had even happened. She doesn’t care about it, at any rate, because her eyes are on Alan now. The show reveals that he was first interested in her prior to his relationship with Judith. Thankfully, there’s nothing coming out of it.

Teri Hatcher As Liz Then

Teri Hatcher As Liz Then

Teri Hatcher As Liz Now

Much like the other girls who starred in the show, Teri Hatcher also had a blooming career after her work in Two and A Half Men. Projects kept coming in after her work in the sitcom. She has worked in various films such as Tomorrow Never Dies, Lois & Clark: The New Adventures of Superman, and Desperate Housewives. Thanks to her role in the Desperate Housewives, she managed to snag a Golden Globe and three SAGs. Lately, the actress was known to be acting in Supergirl and The Odd Couple.

Teri Hatcher As Liz Now

Teri Hatcher As Liz Now

Jaime Pressly As Tammy Then

The viewers of the show have learned that when his girlfriend is introduced, Jake is more similar to his dad than we think. A mother of three, Tammy is the owner of a tattoo parlor. While there is a large age gap between them, the revelation that Jake once went out with her daughter is the cause of the breakup! Aside from that, at some point, she was also involved with Walden. Can it get messier than that, even? We doubt that.

Jaime Pressly As Tammy Then

Jaime Pressly As Tammy Then

Jaime Pressly As Tammy Now

You may know Jaime Pressly as the girl who played Tammy in Two and A Half Men, but a lot of people know her more from the show “My Name is Earl” as Joy Turner. She has garnered a lot of nominations for the Golden Globe Award, and Screen Actors Guild Award. She can also be seen in different films such as Not Another Teen Movie, Joe Dirt, “I Love You, Man” and A Haunted House 2.

Jaime Pressly As Tammy Now

Jaime Pressly As Tammy Now

Judy Greer As Bridget Schmidt Then

When Ashton Kutcher comes in to take over Charlie Sheen, Bridget is introduced. He finds it hard to move on with her after his divorce. Owing to his immaturity, she broke up with him. Despite this, when he has finally begun to move on by dating Zoey instead, she ends up wanting him back.

Judy Greer As Bridget Schmidt Then

Judy Greer As Bridget Schmidt Then

Judy Greer As Bridget Schmidt Now

Aside from her role in the comedy sitcom Two and a Half Men, Judy is also known for landing roles in different projects such as as 27 Dresses, 13 Going on 30, The Wedding Planner, What Women Want, and Love & Other Drugs. The actress also published in 2014 called “I Don’t Know What You Know Me From: Confessions of a Co-Star in 2014.” She is also known to be a casting director, known for casting the film Entourage

Judy Greer As Bridget Schmidt Now

Judy Greer As Bridget Schmidt Now

Sophie Winkleman As Zoey Hyde-Tottingham-Pierce Then

Like we just said, after his divorce from Bridge, Zoey helps Walden get his act together. We are not surprised that the British beauty ends up falling for him! Things go wrong for them, at any rate, when she rejects his proposal. On top of that, he ultimately realizes that while they were still together, she cheated on him with some other guy. By giving her daughter a vicious hound, he gets his revenge on her.

Sophie Winkleman As Zoey Hyde Tottingham Pierce Then

Sophie Winkleman As Zoey Hyde-Tottingham-Pierce Then

Sophie Winkleman As Zoey Hyde-Tottingham-Pierce Now

Aside from her role as Zoey in Two and A Half Men, she is also known for her connection to the British Royal Family. How is she related to them? Sophie Winkleman is the wife of the Queen’s cousin, Lord Frederick Windsor. They were married in the Hampton Court Palace in September 2009. Although belonging to the royal British family, Sophie still acts. She can be seen in Thrust which was released in 2018. Apart from that, she can also be seen in CSI, as well as Miami and Milo Murphy’s Law.

Sophie Winkleman As Zoey Hyde Tottingham Pierce Now

Sophie Winkleman As Zoey Hyde-Tottingham-Pierce Now

Diora Baird As Wanda Then

Although she only had a single episode on the show, with her good looks, Diora Baird was unforgettable. As a model for Guess and Playboy, she got her start. We are not surprised to hear that her career kicked off by doing so! It is possible that you saw her in Wedding Crashers as well.

Diora Baird As Wanda Then

Diora Baird As Wanda Then

Diora Baird As Wanda Now

The actress also appeared in a couple of funny videos on Funny or Die even though she had a short stint on the show. In 2014, in The Ugly Life of a Beautiful Girl, she was cast to play an adult film star. She was a recurring actress in Cocked, apart from that. She has since disclosed that she is in a relationship with Mav Viola, a female comedian.

Diora Baird As Wanda Now

Diora Baird As Wanda Now

Krista Allen As Olivia Pearson Then

When Charlie shows up at a dinner party that his mom is hosting, things go south. He discovers that her boyfriend is the father of somebody he used to date! As usual, between him and Olivia Pearson, things did not end. The dinner was already awkward on its own, but this isn’t just the end of it yet. When Evelyn is dumped by her boyfriend for a different woman, things go further downhill.

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Krista Allen As Olivia Pearson Then

Krista Allen As Olivia Pearson Now

Born in April 5 of 1971, Krista Allen is an American stand-up comic and actress. She is best known for her work in the television series Days of Our Lives and Baywatch and in the Hollywood film The Final Destination. She began her acting career with a role in the soap opera called Days of Our Lives. She recently managed to have a role in the shows Best Mom and Eleven Eleven.

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Krista Allen As Olivia Pearson Now

Kelly Stables As Melissa Then

A female character on the show dates not only Charlie but also Alan more than once. This describes Melissa as well, who we know is Alan’s secretary. She walks out with Charlie at first and only gets together with Alan later on. Actually, when he goes to live with Lyndsey, they’re still together. Uh, oops. Sadly, when she asks Alan for a pay raise and health insurance, the relationship ends.

Kelly Stables As Melissa Then

Kelly Stables As Melissa Then

Kelly Stables As Melissa Now

Kelly Stables is not known for her role in the comedy sitcom Two and A Half Men, but she is better known for her work in the famous horror movie The Ring and also played the role of Samara Morgan the evil, in The Ring Two. She is also known to star in various plays, with the biggest one being Wendy in Peter Pan, and Sleeping Beauty in Thousand Oaks Civic Light Opera. She has also worked as a voice actress for W.I.T.C.H. and Cloudy with a Chance of Meatballs.

Kelly Stables As Melissa Now

Kelly Stables As Melissa Now


Heather Locklear As Laura Then

The character of Laura was played in the show by Heather Locker. She was the divorce lawyer for Alan. He decided to pursue Laura no matter what might happen, with Charlie hitting on any woman he wants. Charlie made a serious error, however, in constantly lying to her while she was dating her. Laura took her revenge after Charlie and Laura broke up by ruining Alan’s divorce settlement, forcing him to look for a new lawyer.

Heather Locklear As Laura Then

Heather Locklear As Laura Then

Heather Locklear As Laura Now

Heather Locker was already famous before she joined the comedy sitcom Two and A Half Men, in fact, during the 80’s and the 90’s no other famous name could be heard except for Heather Locker’s. She is known for her performances in Spin City and Melrose Place. She regularly used to be found on tabloids due to her controversial divorce and various health issues. Some of her recent works include Too Close To Home, Fresh Off The Boat, and Franklin & Bash, among many others.

Heather Locklear As Laura Now

Heather Locklear As Laura Now

Kimberly Quinn As Donna Then

Donna first meets Alan on a blind date, where they instantly hit it off. However, after the two dated for some time, Alan decides to end the relationship because he feels he is bored of the situation. Naturally, Alan goes to his brother Charlie where he suggests that he lets Donna down easily. But she does not take the news well and ends up crying hysterically.

Kimberly Quinn As Donna Then

Kimberly Quinn As Donna Then

Kimberly Quinn As Donna Now

Since her time on TAAHM, the stunning actress has continued to work in the industry. She has appeared in Twisted, NYPD Blue, CSI and Terriers. Quinn is married to director Theodore Melfi. Together they own a production company called Goldenlight Films.

Kimberly Quinn As Donna Now

Kimberly Quinn As Donna Now


Denise Richards As Lisa Then

For true fans of the show, you will know that Charlie does not call too many women his girlfriend, however, Lisa was one of the lucky few. At some point, she even lives in Charlie’s house. Despite that, when their relationship starts to get quite serious, Charlie gets nervous and breaks up with her. Later on, Lisa ties the knot with someone new but promises to call Charlie if she gets divorced…what a way to start a marriage! As expected, she gets divorced and finds her way back with Charlie but in the end, things didn’t work out.

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Denise Richards As Lisa Then

Denise Richards As Lisa Now

At the time that Richards played Lisa, she was in fact married to Charlie Sheen in real life. So, yes, the chemistry was all real! The two were married from 2002 until 2005. The couple had two daughters together, Lola and Sam. Since her time on TAAHM, Richards has appeared on several big and small screen projects. She also starred on the E! reality show called Denise Richards: It’s Complicated. 

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Denise Richards As Lisa Now

Kristin Dattilo As Cindy Then

Next up we have another one of Charlie’s women, Cindy. Although Charlie is known to charm many ladies into his bed, Cindy is not fooled by his behavior. But things get even more interesting, when Alan’s son, Jake starts to develop a crush on Cindy. And then, in a surprising plot twist, Judith and Cindy meet and form a bond over their daddy issues. Alan somehow catches on and gets suspicious about this newly formed friendship.

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Kristin Dattilo As Cindy Then

Kristin Dattilo As Cindy Now

This gorgeous actress has also starred on The Chris Isaak Show from 2001 to 2004. 50-year-old Dattilo has also appeared on TV shows like Beverly Hills, 90210, CSI, Grounded for Life, Dexter, Veronica Mars, and Dexter. Most recently she played Maddie Harmon in the movie How to Get Rid of a Body (and still be friends). In 2005, she married Jason Keller, who is the father of her two kids.

 

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Kristin Dattilo As Cindy Now

 

Courtney Thorne-Smith As Lyndsey McElroy Then

Lyndsey McElroy is first seen on the 7th season as Alan’s love interest. Alan and Lyndsey first meet when their sons become friends. However, things don’t get too serious as they have an on-and-off relationship. The number of times these two broke up and got back together was countless. Unfortunately, Lyndsey has a drinking problem and later tries to get with Walden.

Courtney Thorne Smith As Lyndsey McElroy Then

Courtney Thorne-Smith As Lyndsey McElroy Then

Courtney Thorne-Smith As Lyndsey McElroy Now

Actress Courtney Thorne-Smith brought Lyndsey McElroy to life on the show. But before this, she appeared in Ally McBeal from 1997 to 2002. Over the years Courtney’s acting career has since slowed down as she focuses on her family and personal life. She is married to Roger Fishman with whom she has a 9-year -old son, Jacob.

Courtney Thorne Smith As Lyndsey McElroy Now

Courtney Thorne-Smith As Lyndsey McElroy Now

April Bowlby As Kandi Then

Kandi is a 22-year-old girl who has a reputation for being very promiscuous. She first gets together with Charlie, later hooks up with Alan, and then with Judith’s divorce lawyer. However, it gets to a point where Alan and Kandi get married in Las Vegas, and she then obviously moves in with him. Once she lands an acting job on a detective show, the two break up.

April Bowlby As Kandi Then

April Bowlby As Kandi Then

April Bowlby As Kandi Now

Actress April Bowlby is now 40 years old and still so well-known for her time on Two and a Half Men. However, she has also appeared on the shows such as How I Met Your Mother,[3] and has made appearances in CSI, Psych, The Big Bang Theory, How I Met Your Mother, and CSI: NY. Bowlby also decided to ditch he red hair and go blonde.

April Bowlby As Kandi Now

April Bowlby As Kandi Now

Brooke Shields As Danielle Stewart Then

Danielle Stewart is the Harpers’ neighbor, but both brothers end up falling for the tall beauty. She first dates Alan, however, Charlie finds her extremely alluring and tries his best to go after her. Alan and Charlie quarrel over who gets to date her in the end, but ultimately Danielle decides to leave them both. Both of them were completely shocked, but things worked out for the best.

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Brooke Shields As Danielle Stewart Then

Brooke Shields As Danielle Stewart Now

Actress, Brooke Shields began her acting career when she was just a child, which means she has had a long-spanning career. She was definitely a household name even before she landed on the hit comedy series. The beautiful 56-year-old has also appeared in projects like Hannah Montana, Law & Order: Criminal Intent, and The Middle. She also had a recurring part in Law and Order: Special Victims Unit. Shields is also a mother of two to Rowan and Grier.

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Brooke Shields As Danielle Stewart Now

Megan Fox as Prudence Then

Megan Fox plays Prudence who is Berta’s 16-year-old granddaughter. As she is so gorgeous, it was only a matter of time before someone fell for her. Despite her young age, both Alan and Jake develop a crush on her. Throughout everything that was going on, Berta doesn’t trust Prudence which is what she needs to keep an eye out for her. After an argument between Berta and Prudence, Prudence plans on running away to Las Vegas to get married to her boyfriend Freddie. Luckily, Bertha shows up with Prudence’s mother, Cheryl Ann and the two stop the teenager.

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Megan Fox as Prudence Then

Megan Fox as Prudence Now

Megan Fox is both an actress and model and is also said to be one of the most beautiful women in the world. She has appeared in numerous magazines such as Maxim, Rolling Stone, and FHM. But some of her other projects have included starring This Is 40, The Help, Hope & Faith, and New Girl. 35 year old, Megan Fox is also a mother of 3 children.

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Megan Fox as Prudence Now

 

Miley Cyrus as Missi  Then

Missi who is played by Miley Cyrus is the daughter of one of Walden’s friends who came to visit him. When Jake comes home from the army for the weekend he meets Missi. The two instantly hit it off and quickly form a relationship, even though Missi had a boyfriend. Secretly, Jake leaves the army just to be with Missi. Jake confesses his love for his new girlfriends, but Missi gets super uncomfortable and convinces him to go back to the army.

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Miley Cyrus as Missi  Then

Miley Cyrus as Missi – Now

There aren’t that many people who haven’t heard of Miley Cyrus, most of us know her from Hannah Montana. Currrently the pop star is 28 years old and has a very successful career and is famous all over the world. Cyrus has also acted in films such as Big Fish, The Night Before, and Guardians of The Galaxy Vol.2. Did you know that Dolly Parton is Miley’s godmother?

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Miley Cyrus as Missi – Now

Stephany Jacobsen as Penelope – Then

Not too long after Walden buys Charlie’s house after his death, a strange woman dressed in a bikini comes to the door looking for Charlie. Penelope very quickly sadly learns about Charlie’s death, she seems very upset but then her eye catches Walden. As the two begin talking, Walden’s ex-wife, Bridget, arrives at the house so she could talk to him but is resentful to find Penelope there. Fortunately, Alan manages to save the day by pretending Penelope was his girlfriend.

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Stephany Jacobsen as Penelope – Then

 

Stephany Jacobsen as Penelope  Now

Before she starred on Two and a Half Men, Stephany was actually famous for her role as Charlotte Adams in the drama series Home and Away. The Hong Kong-born Australian actress also appeared in Melrose Place, Hawaii Five-0, Revenge, and NCIS. Jacobsen is 41 years old and definitely seems to be getting more and more successful as the years go on.

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Stephany Jacobsen as Penelope  Now

Sara Rue as Naomi  Then

Sara Rue plays Naomi who is the daughter of Berta. Berta sees Naomi as her pride and joy, even though she is both pregnant and unemployed. Due to her situation, Naomi is forced to move in with her mother for support. Within a matter of no time, Naomi develops feelings for Alan. In the middle of their first kissing scene, Naomi goes into labor. After giving birth to a baby girl, she and Alan decide to keep their relationship a secret. Berta soon finds out and to everyone’s surprise, she was actually happy about it, since Alan was the kindest man her daughter had ever dated. Sadly, the relationship falls apart after Naomi’s ex and her daughter’s biological father returns, and the two get back together.

 

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Sara Rue as Naomi Then

Sara Rue as Naomi Now

Sara Rue is an American actress who is actually more well-known for her appearances on Popular and Less Than Perfect. Rue also starred in many TV shows, some of which include, The Big Bang Theor, The Simple Life, ER, and The Rookie. She has also had several movie roles in films such as Pearl Harbor and The Ring. Rue is the mother of two daughters.

 

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Sara Rue as Naomi Now

 

Rachel Cannon as Chloe – Then

Rachel Cannon stars as Chloe who is one of Charlie’s girlfriends. However, Charlie does everything in his power to get rid of her. Then, when a young and handsome handyman called Fernando (who was played by Enrique Iglesias) comes to Charlie’s house to repair his desk, Charlie has a change of heart. Without Charlie realizing it, Chloe falls for Fernando which makes Charlie extremely jealous. In the end, Chloe leaves Charlie for Fernando even though Charlie tries to get back with Chloe by bribing her.

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Rachel Cannon as Chloe

Rachel Cannon as Chloe Now

Actress Rachel Cannon is no stranger to TV shows and has had many minor roles in various successful series. Some of the projects that she has appeared on include, Mad Men, Ghost Whisperer, Underemployed, and The Big Band Theory. Sadly for us, Cannon hasn’t had too many major roles, but we still have a lot of hope. Her most recent role was in the ABC sitcom Fresh Off the Boat, where she has been playing Deidre for the last two years.

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Rachel Cannon as Chloe Now

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