Office Space Turns 20! See Jennifer Aniston and the Rest of the Cast Then and Now

The now-classic workplace comedy was originally a flop at the box office when it came out in 1999, grossing only $10.8 million. The movie satirized everyday workplace life, focusing on a group of employees at a software company who are fed up with their 9-to-5 jobs.

Aniston played Joanna, a restaurant waitress who loves kung fu. The actress starred in Office Space during the middle of Friends' 10 season run, where she became famous for her portrayal of Rachel Green. After Friends ended, Aniston went on to star in numerous movies: most recently, Netflix's Dumplin'.

Livingston played Peter Gibbons in Office Space, a frustrated employee who hates his job. Since starring in the comedy, Livingston has gone on to have a successful career in both television and film, appearing in movies like Tully and The Conjuring. He is currently starring on ABC's A Million Little Things.

After starring as Office Space's company vice president Bill Lumbergh, Cole went on to have a long and successful career in televsion; he has starred on Veep, The Good Wife, Bob's Burgers, Suits and Family Guy, just to name a few.

Judge, who wrote Office Space and played Stan, Jennifer Aniston's character's boss in the film, has had a long career in both writing and acting. Judge is the creator of the television series Beavis and Butt-Head, and the co-creator of King of the Hill and Silicon Valley.

After portraying Milton Waddams in Office Space, Root went on to star in comedy television shows including Barry and Adventure Time. He's also acted in his fair share of drama films — including Get Out, Selma, and On the Basis of Sex.