Missi Pyle As Miss Pasternak Then
Missi Pyle portrayed Miss Pasternak, the teacher who suspended Jake when he gave her the finger. After that, Charlie began to date her, and suddenly Jake’s grades were on the rise. Shortly after, the relationship soured when she revealed her past to Charlie.
Missi Pyle As Miss Pasternak Then
Missi Pyle As Miss Pasternak Now
Missi Pyle has appeared in many other TV shows including My Name is Earl, Two Broke Girls, Another Period, Mad About You, and Friends. Outside of her acting work, Pyle is also a musician and is a part of a duo called Smith & Pyle.
Missi Pyle As Miss Pasternak Now
Marin Hinkle As Judith Harper-Melnick Then
Actress Marin Hinkle portrayed Judith Harper-Melnick, Alan’s ex-wife. Despite their difficult past, they tried to co-parent Jake, which led to many arguments. Things grew even more complicated when she married Jake’s doctor.
Marin Hinkle As Judith Harper Melnick Then
Marin Hinkle As Judith Harper-Melnick Now
After appearing in Two and a Half Men, Marin Hinkle appeared in any other shows include Castle and a starring role in Madam Secretary. She later appeared in hit TV shows Shameless and Homeland. She is married and has one child.
Marin Hinkle As Judith Harper Melnick Now
Emmanuelle Vaugier As Mia Then
Emmanuelle Vaugier portrayed dance teacher Mia who Charlie relentlessly pursued. She agreed to go out with him if he agreed to give up smoking, drinking, and eating meat, which he agreed to do. However, the relationship came to an end when she found out he was doing these things behind her back.
Emmanuelle Vaugier As Mia Then
Emmanuelle Vaugier As Mia Now
After her role on TAAHM, Vaugier went on to act in more TV shows like Mistresses, Lost Girl, and One Tree Hill. She has also starred in films like Wash Away, Destruction Los Angeles, and Masks Don’t Lie.
Emmanuelle Vaugier As Mia Now
Holland Taylor As Evelyn Harper Then
Holland Taylor played Charlie and Alan’s mother Evelyn Harper. The two did not have an easy relationship with their mother, as she had a reputation for being a bit of a gold digger and looking for older men to date. She was certainly a fan favorite.
Holland Taylor As Evelyn Harper Then
Holland Taylor As Evelyn Harper Now
Holland Taylor is one of the most successful actresses in Hollywood. She has been active in the industry since the 1980’s and has been given numerous awards, including four Best Supporting Actress nominations for her role on the show. She also had an unforgettable role in Legally Blonde.
Holland Taylor As Evelyn Harper Now
Melanie Lynskey As Rose Then
Melanie Lynskey played Rose, Charlie’s neighbor and stalker. She continuously tried to get his attention, and eventually he gives in. Charlie eventually agrees to marry her and run off to Paris. Sadly for Rose, things did not pan out as Charlie ended up dying before the marriage could happen.
Melanie Lynskey As Rose Then
Melanie Lynskey As Rose Now
Lynskey has appeared in many films which include Sweet Home Alabama, Coyote Ugly, and Heavenly Creatures. She later appeared in Hello I Must Be Going, I Don’t Feel At Home In This World Anymore, and The Intervention. She is engaged to Jason Ritter.
Melanie Lynskey As Rose Now
Jennifer Taylor As Chelsea Melini Then
Jennifer Taylor portrays Chelsea Melini, the first woman that Charlie ever told he loved. He accidentally blurted it out, and ends up getting emotionally attached. Eventually, Chelsea leaves Charlie for Alan’s lawyer.
Jennifer Taylor As Chelsea Melini Then
Jennifer Taylor As Chelsea Melini Now
After playing Chelsea Melini, Jennifer Taylor appeared in many other TV shows and films. She was featured in TV shows Mom, Shameless, and NCIS. She is married to musician Paul Taylor, and the couple has two children.
Jennifer Taylor As Chelsea Melini Now
Allison Janney As Beverly Then
Allison Janney plays beverly, a woman that Alan meets online. He told her that he owns the home in order to impress her. The two begin a relationship until an awkward incident involving Charlie walking in on them and Alan being tied up.
Allison Janney As Beverly Then
Jeri Ryan As Sherri Then
Jeri Ryan portrayed Sherri on Two and a Half Men, Charlie’s girlfriend. Sherri doesn’t fall for the same types of ruses that Charlie uses on other women, and eventually their relationship falls apart. She tried to pursue Alan next, but to no avail.
Jeri Ryan As Sherri Then
Jeri Ryan As Sherri Now
Jeri Ryan is best known for her role on Star Trek: Voyager, where she played Seven of Nine. She also starred in Leverage, Body of Proof, and Major Crimes. She is married to Christophe Eme, and the two have two children together.
Jeri Ryan As Sherri Now
Kimberly Williams-Paisley As Gretchen Martin Then
Kimberly Williams-Paisley portrayed Gretchen Martin, Larry’s sister in the eleventh season of the show. When Alan begins to dat her, he tells her that he owns the apartment and he doesn’t live with his brother. Eventually she figures out that he is lying to her and they break up.
Kimberly Williams Paisley As Gretchen Martin Then
Kimberly Williams-Paisley As Gretchen Martin Now
Williams-Paisley has been acting ever since she was a child. She appeared in Father of the Bride and in eight years on TV show According to Jim. She married country star Brad Paisley in 2003.
Kimberly Williams Paisley As Gretchen Martin Now
Ming-Na Wen As Linda Harris Then
Ming-na Wen portrays Linda Harris who Charlie falls for. However, she continually rejects him. After Charlie gets caught drunk driving and appears in court, he faces the judge, who is none other than Linda.
Ming Na Wen As Linda Harris Then
Ming-Na Wen As Linda Harris Now
Ming-Na Wen had her first big break when she voiced Fa Mulan in the beloved animated Disney film. She also has done voice work for Sofia the First, and Wreck It Ralph 2: Ralph Breaks the Internet. She starred in TV shows SGU Stargate Universe and also Eureka.
Ming Na Wen As Linda Harris Now
Gail O’Grady As Mandi Then
Gail O’Grady plays the role of Mandi, who ended up at Charlie and Alan’s house while looking for her daughter, Kandi. She ends up spending the day with Charlie.
Gail O’Grady As Mandi Then
Gail O’Grady As Mandi Now
Actress Gail O’Grady also appeared in American Dreams, Ms. Fields, and Revenge. She has been married a total of sic times. Her last relationship, which was with John Stamatakis, ended in 2008.
Gail O’Grady As Mandi Now
Tammy Lauren As Shannon Then
Tammy Lauren portrayed Shannon and gets involved with her to get Judith jealous, and for Shannon to get back at her ex Herb. However, their plan did not pan out, and neither one gets their ex back.
Tammy Lauren As Shannon Then
Tammy Lauren As Shannon Now
Tammy Lauren played Maggie Sullivan on The Young and the Restless. She was also on Madison Avery and Criminal Minds. She is married to fellow actor Guri Weinberg.
Tammy Lauren As Shannon Now
Justine Eyre As Gabrielle Then
Justine Eyre played Gabrielle, a woman that Charlie is dating. When Alan finds out that Charlie stole his high school girlfriend, Alan tries to steal Gabrielle away. After regretting this, Alan then comes home to find Charlie with his high school girlfriend once again.
Justine Eyre As Gabrielle Then
Justine Eyre As Gabrielle Now
Actress and model Justine Eyre secured other guest roles on TV shows after appearing in Two and A Half Men. She starred in shows Mad Men, CSI: Miami, and The Secret Life of the American Teenager. She is married to screenwriter John Allen Nelson.
Justine Eyre As Gabrielle Now
Maggie Lawson As Ms. McMartin Then
Maggie Lawson portrayed Ms. McMartin, the social worker who is involved when Walden and Alan are looking to adopt. Ms. McMartin later realizes that the two lied on their application, but she forgives them and first dates Alan, later moving on to Walden.
Maggie Lawson As Ms. McMartin Then
Maggie Lawson As Ms. McMartin Now
Lawson has appeared on shows like The Great Outdoors, Psych, and Angel From Hell. She also appeared in the film adaptation of Psych. Later, in 2019, she appeared in Lethal Weapon. She married Ben Koldyke in 2015, but filed for divorce from him in 2017.
Maggie Lawson As Ms. McMartin Now
Conchata Ferrell As Berta Then
Conchata Ferrel portrayed Berta, a motherly figure who has consistently been around for the guys and even stayed with Alan even after Charlie’s death. She has appeared in every single season of the show.
Conchata Ferrell As Berta Then
Conchata Ferrell As Berta Now
Although Conchata Ferrell is best known for her role as Berta, for which she was nominated for a Primetime Emmy for Outstanding Supporting Actress in a Comedy Series, she has also been acting on Broadway. She later appeared alongside Ashton Kutcher once again on Netflix show The Ranch.
Conchata Ferrell As Berta Now
Jenny McCarthy As Courtney Leopold Then
Charlie’s mother begins dating Courtney Leopold’s father when he begins to date Courtney herself. Alan realizes that she is trying to get money and a Ferrari out of Charlie and warns him.
Jenny McCarthy As Courtney Leopold Then
Teri Hatcher As Liz Then
Teri Hatcher appears as Liz, Judith’s sister. She gets together with Charlie at Alan and Judith’s wedding, but Charlie doesn’t remember it. She later pursues Alan, but he does not go for her.
Teri Hatcher As Liz Then
Teri Hatcher As Liz Now
Teri Hatcher has appeared in many TV shows including Tomorrow Never Dies and Lois & Clark: The New Adventures of Superman. She is best known for her role on hit TV drama Desperate Housewives. She later appeared in The Odd Couple and Supergirl.
Teri Hatcher As Liz Now
Jaime Pressly As Tammy Then
Jaime Pressly stars as Tammy, Jake’s mature girlfriend who runs a tattoo shop and has three children. Later the two break up after they discover that Jake dated her daughter Ashley. Tammy later hooks up with Walden…talk about complicated!
Jaime Pressly As Tammy Then
Jaime Pressly As Tammy Now
Jaime Pressly appeared in My Name Is Earl as Joy, a role that earned her a Primetime Emmy Award for Outstanding Supporting Actress in a Comedy Series. She also starred in films like Not Another Teen Movie, I Love You Man, Joe Dirt, and A Haunted House 2.
Jaime Pressly As Tammy Now
Judy Greer As Bridget Schmidt Then
Judy Greer appears on Two and a Half Men as Bridget Schmidt, a woman that Walden dates. At first, she thinks that he is too immature for her, but she later changes her mind when he began to date Zoey.
Judy Greer As Bridget Schmidt Then
Judy Greer As Bridget Schmidt Now
Judy Greer has appeared in many films which include 27 Dresses, 13 Going on 30, What Women Want, Love & Other Drugs, and The Wedding Planner. In 2014, she released a book entitled I Don’t Know What You Know From Me: Confessions of a Co-Star.
Judy Greer As Bridget Schmidt Now
