Office Space is a cult classic and one of Mike Judge's earliest post-Beavis and Butthead projects besides King Of The Hill. It also features Jennifer Aniston at the height of her popularity while making Friends as well as a cadre of some of Hollywood's most prominent voice actors, like David Herman, Diedrich Brader, and Gary Cole.

Related: What Is The Most Famous Episode Of 'King Of The Hill'?

Although it only made $12 million at the box office against a $10 million budget, making it a flop in the eyes of producers, it eventually became a fan favorite thanks to DVD sales, regular syndication on television, and streaming services. The cast of the classic comedy has all created successful careers following the film, with Jennifer Aniston becoming the richest alumni of the cast.

8 Ajay Naidu - $1 million

Ajay Naidu played Samir, one of the cohorts of Peter Gibbons, the film's main character who plans along with Samir to con their office out of millions using an "undetectable" computer virus. Before Office Space, he had been nominated for an Independent Spirit award for his role in SubUrbia. He continues to act in both television and in film and in 2010 his directorial debut Asheswas released on the festival circuit.

7 David Herman - $3 million

Fans of MadTV will immediately recognize Herman from his tenure as one of the original cast members of the classic sketch comedy show. Herman is a regular collaborator with Mike Judge and has appeared in films and shows created by Judge like King of The Hill and Idiocracy. Herman continues to voice act, he is the voice of Mr. Frond on Bob's Burgers and other characters on the show.

Related: 10 Stars Who Have Voiced Characters On 'Bob's Burgers'

6 Gary Cole - $5 million

Cole, AKA, Lumberg, is also a prominent voice actor who has done spots on King of the Hill as well as Bob's Burgers and several Adult Swim shows. Cole was also in The Brady Bunch movie of the 1990s and played Mike Brady, a voice he has also done frequently for Family Guy, another cartoon he is a regular on. Films that feature Cole include Dodgeball, Talledega Nights, and Pineapple Express.

5 Stephen Root - $6 million

King of The Hill fans might know Stephen Root by his character from the show, Bill Dauterive. Root is regularly cast as meek pushovers, as he was in Dodgeball and as Milton in Office Space. He has also done dramatic roles, horror fans might recognize him as the blind aristocrat from Jordan Peele's breakout film Get Out. He is now a regular on the hit HBO series Barry.

4 Ron Livingston - $6 million

Livingston was the film's star, Peter Gibbons, the disgruntled employee who is hypnotized into being such a chill guy that the workplace he hates ends up loving him, giving him promotions and, in turn, the perfect cover for his con. After the film, Livingston went on to be in Band Of Brothers, the classic WWII miniseries, shows like Loudermilk, and films like Tully. He has been a regular on the show A Million Little Things since 2018.

3 Diedrich Bader - $6 million

Bader played Lawrence, Brader's mustachioed and super manly neighbor. Brader has been in all sorts of comedy shows and films. He played Oswald on The Drew Carey show for its entire run, he had guest spots on shows like Reno 911, he was the martial arts instructor in Napolean Dynamite, and has a comedy filmography too long to summarize in a single list like this one. Bader is also a prominent voice actor, who has loaned his talents to everything from children's shows to FOX's Animation Domination shows. He is also frequently used by DC as the voice of Batman in several animated feature films.

2 Mike Judge - $75 million

Judge was in the movie and is practically unrecognizable as Stan, the manager of Chotchkies who chastises Jennifer Aniston for "her lack of flair," perfectly personifying the tediousness that servers at chain restaurants sometimes have to deal with. Judge has directed several successful films and is the creator of shows like King of the Hill, Beavis and Butthead, and Silicon Valley. After the end of Silicon Valley, Judge rebooted Beavis and Butthead in the summer of 2022.

Related: Beavis and Butt-Head's Biggest Controversy Turned Out To Be A Lie

1 Jennifer Aniston - $300 million

It should come as no surprise that the member of the Office Space cast who was on a sitcom that paid her $1 million per episode and is now an international box office magnet is the richest member of the cast. Aniston's one of the most popular actors in Hollywood and has been a tabloid favorite thanks to her former relationship with Brad Pitt and other stars for decades now. Aniston returned to television on her Apple+ series The Morning Show, which she stars in with Reese Witherspoon. Some of Aniston's other major works, besides Office Space and Friends are We Are The Millers, The Break Up, and Just Go With It. Fun fact about this incredibly famous actress, her first movie ever was barely noticeable background roll in Mac and Me, a notoriously awful E.T. rip off that is widely considered one of the worst films in history.

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