‘Two and a Half Men’ celebrates 20th anniversary: The cast then and now


Two and a Half Men” is celebrating its 20th anniversary.

The show followed the life of Charlie Harper, whose world gets turned upside down when his brother Alan and his son Jake move in with him after Alan gets divorced. 

Here is what the show’s biggest stars are up to now.

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Charlie Sheen

Charlie Sheen already had a successful career before getting cast as the lead in “Two and a Half Men.” (Getty Images)

Prior to starring as Charlie Harper on “Two and a Half Men,” Charlie Sheen was already a successful actor, having appeared in “Born on the Fourth of July,” “Platoon,” “The Rookie” and “Spin City.” His role on “Two and a Half Men” earned him two Golden Globe and four Emmy Award nominations. He also starred in “Scary Movie 3” and “Scary Movie 4,” and “Due Date.” 

In 2011, Sheen was fired and banned from the Warner Bros. lot while the show was on hiatus, due to his struggles with substance abuse. He got sober in December 2017, telling Jay Leno on an episode of “Jay Leno’s Garage,” he had an “epiphany” one day and realized he needed to change, and has not drank since.

His big return to TV was in the series, “Anger Management,” which ran from 2012 to 2014. Throughout the run of the show, he also starred in “Madea’s Witness Protection,” “Scary Movie V” and “Machete Kills.”

Sheen was married to Donna Peele from 1995 to 1996. He then married Denise Richards from 2002 to 2006. They have two daughters, Sami and Lola. He then married Brooke Mueller from 2008 to 2011, and the two have twin sons, Bob and Max. He also shares his daughter, Cassandra Estevez, with his high school girlfriend.

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Jon Cryer

John Cryer then and now split

Jon Cryer’s breakthrough film performance was in “Pretty In Pink,” before starring in “Two and a Half Men.” (Getty Images)

Jon Cryer started his professional career on Broadway before he made his film breakthrough as Philip F. “Duckie” Dale in John Hughes’ movie “Pretty In Pink.” He gained further recognition when he landed the role of Alan Harper in “Two and a Half Men.”

He also appeared in “CSI: Crime Scene Investigation,” “Weather Girl,” “Due Date,” “Hit by Lightning,” “NCIS,” “The Great Indoors,” “The Ranch” and “Justice League Action.” He later appeared in “Ryan Hansen Solves Crimes on Television,” “Batwomen,” “The Flash,” “Arrow” and “DC’s Legends of Tomorrow.” Most recently, he appeared in “The Kominsky Method,” “18 ½” and “Supergirl.” 

Cryer was married to Sarah Trigger from 1999 to 2004, with the two sharing a son together, Charlie Austin. He then married Lisa Joyner in 2007, and the couple adopted a baby girl named Daisy.

Angus T. Jones

Angus T. Jones then and now split

When Angus T. Jones turned 17, he became the highest paid child actor, starring as Jake Harper on “Two and a Half Men.” (Getty Images/Coleman-Rayner)

Angus T. Jones’ role as Jake Harper on “Two and a Half Men,” made him the highest paid child actor by the time he turned 17. He played the character from 2003 to 2014, with his final episodes airing in 2015. Prior to starring on the show, he had appeared in “See Spot Run,” “The Rookie” and “Bringing Down the House.”

In 2012, Jones revealed he was baptized into the Seventh-day Adventist Church. In a video for the Forerunner Chronicles, a Christian group, Jones bashed the show, and said he no longer wanted to be a part of it. 

“If you watch ‘Two and a Half Men,’ please stop watching ‘Two and a Half Men.’ I’m on ‘Two and a Half Men’ and I don’t want to be on it,” he said in the video. “Please stop watching it and filling your head with filth. People say it’s just entertainment. Do some research on the effects of television and your brain, and I promise you, you’ll have a decision to make when it comes to television, especially with what you watch.” 

He did not appear in the show’s 11th season, however he did return for a cameo in the show’s season finale. Following his departure from the show, Jones appeared in one episode of the miniseries “Horace and Pete.”

Ashton Kutcher

Ashton Kutcher then and now split

Ashton Kutcher had starred on the successful show “That ’70s Show,” before replacing Charlie Sheen on “Two and a Half Men.” (Getty Images)

Ashton Kutcher was hired as Sheen’s replacement after he was fired, playing Walden Schmidt on “Two and a Hald Men.” Prior to that, he starred in “The Butterfly Effect,” “Punk’d,” “The Guardian,” “What Happens in Vegas” and “Valentine’s Day.”

He went on to star in “Jobs,” “No Strings Attached,” “Annie” and “The Ranch.” Most recently, he starred in “Vengeance,” “Stoner Cats,” “Your Place or Mine” and appeared in the first episode of “That ‘90s Show,” reprising his breakout role in “That ’70s Show.” He has also found success investing in startup companies and founded an international anti-human trafficking organization, called Thorn: Digital Defenders of Children.

Kutcher was married to Demi Moore from 2005 to 2013. He then married Mila Kunis in 2015 and has two children with her, a daughter named Wyatt and a son named Dimitri.

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He and Kunis recently received backlash when it was revealed they wrote character references on behalf of their former co-star, Danny Masterson, who was being sentenced for two rape convictions. In his letter, Kutcher called Masterson a man of “innate goodness,” who is not “an ongoing harm to society.” He and Kunis would later apologize and Kutcher also resigned as chairman of the board of Thorn.

Conchata Ferrell

Conchata Ferrell then and now split

Conchata Ferrell had a successful career in both television and film, before playing Berta in “Two and a Half Man.” (Conchata Ferrell)

Conchata Ferrell is best known for playing Berta in “Two and a Half Men.” Throughout her career she has received three Emmy nominations, two of which were for “Two and a Half Men.”

Ferrell also appeared in “Becker,” “Judging Amy,” “Surviving Eden,” “Kabluey,” “Frankenweenie” and “Wishin’ and Hopin.” She later appeared in “Krampus,” “Postal Jerks” and “Grace and Frankie.” Her final on-screen roles include “The Axe Murders of Villisca,” “The Ranch,” “A Very Nutty Christmas” and “Deported.”

She married Arnie Anderson in 1986, and together they had a daughter named Samantha. She also had two stepdaughters, Lisa and Caitlin Anderson. Ferrell passed away in October 2020 following complications due to cardiac arrest.

Marin Hinkle

Marin Hinkle then and now split

Marin Hinkle was on the ABC drama “Once and Again” before starring in “Two and a Half Men.” (Getty Images)

Marin Hinkle was known for her role in “Once and Again,” before she was cast as Judith Harper-Melnick on “Two and a Half Men.”

She also starred in “Friends with Money,” “Quarantine,” “Imagine That,” “Deception,” “Jumanji: Welcome to the Jungle,” “Homeland,” “Speechless,” “Madame Secretary” and “Jumanji: The Next Level.” She then starred on “The Marvelous Mrs. Maisel” for five seasons, earning two Emmy nominations and two SAG Award wins.

Hinkle has been married to Randall Sommer for 25 years, getting married in 1998. They have one son, named Ben.

Melanie Lynskey

Melanie Lynskey then and now split

Melanie Lynskey got her start on the Percy Jackson movie “Heavenly Creatures” in 1994. (Getty Images)

Melanie Lynskey got her start in the 1994 movie “Heavenly Creatures,” before getting the part of Rose in “Two and a Half Men.” 

She also starred in “Shattered Glass,” “Flag of Our Fathers,” “Up In the Air,” “The Informant,” “The Perks of Being a Wallflower” and “Hello I Must Be Going.” She later appeared in “Togetherness,” “Mrs. America,” Don’t Look Up,” “Candy,” “The Last of Us” and “Yellowjackets.” 

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Lynskey was married to Jimmi Simpson from 2007 to 2014. She then married Jason Ritter in 2020, and the two share a daughter, named Kahikatea.

Amber Tamblyn

Amber Tamblyn then and now split

Amber Tamblyn got her start at 11-years-old when she starred on the soap opera “General Hospital.” (Getty Images)

Amber Tamblyn began starring on “Two and a Half Men” in 2013, playing Jenny Harper, Sheen’s character’s long-lost daughter. Prior to appearing on the show, Tamblyn had starred in “The Sisterhood of the Traveling Pants” and its sequel, “The Ring,” “House” and “General Hospital.”

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She was on the show for two seasons, making her first appearance on the first episode of season 11. During this time, she also starred in “3 Nights in the Desert,” “X/Y” and “Growing Up and Other Lies.” Most recently, she has starred in “Y: The Last Man,” “Inside Amy Schumer” and “You Hurt My Feelings.”

Tamblyn married actor David Cross in October 2012, and in 2017 they announced they had secretly welcomed a daughter named Marlow.

Holland Taylor

Holland Taylor then and now split

Holland Taylor started her career in theater, having since gone on to win an Emmy Award and getting nominated for seven others. (Getty Images)

Holland Taylor had been acting both on stage an on-screen for decades before starring as Evelyn Harper on “Two and a Half Men.” Throughout her career she has received seven Emmy nominations, and one win.  

She also appeared in “The Wedding Date,” “Legally Blonde,” “The Practice,” and “The Chair” among others. 

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In March 2016, it was confirmed she was in a relationship with was actress Sarah Paulson. During an August 2020 interview on the “LGBTQ&A” podcast, Taylor revealed that she identifies as gay.



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