Office Space facts: Office Space 20th anniversary

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Office Space 20 years later

Van Redin

The highly-ironic comedy is solidly considered a success in 2019, but two decades ago its fate was much more uncertain. Most fans know the story behind its slow rise to fame, but the real story of how it all came together is so much more detailed. To celebrate the movie’s 20th anniversary, EW talked to everyone from the stars to the producer to the network execs. Ahead, some of the craziest things we discovered — and be sure to check out our full oral history with Mike Judge and the cast.

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Fox wanted Mike Judge to pursue Matt Damon and Ben Affleck as stars

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And yes, this was post-Good Will Hunting success. As everyone knows, they wound up tampering their expectations slightly.

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The studio asked Ron Livingston to fast before his screen test

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The actor, who starred as Peter, spent the weekend prior to the big day jumping rope — but only made it halfway through the fast.

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Jennifer Aniston and David Herman went to high school together

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“I was a sophomore when he was a senior,” she told EW of the actor who portrayed the fictional Michael Bolton. “He was a quiet, genius actor-type back then. I was sort of madly in love with him, and also terrified of him.”

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Owen Wilson, Vince Vaughn, and Kate Hudson all auditioned for roles

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In a shocking twist, those auditions were unsuccessful.

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The "flair" storyline was added at the last minute

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It was meant to give Jennifer Aniston’s storyline more heft — she was the biggest star among the cast, after all.

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Jim Carrey and Chris Rock were some of the movie's earliest fans

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Even though it was a box office flop, Mike Judge got a dinner invitation from Carrey and a glowing voicemail from the Rock.

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Madonna had the hots for Michael Bolton

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She told creator Mike Judge during a dinner: “That Michael Bolton guy is my favorite character. There’s something sexy about how angry he is.”

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To this day, people still ask Jennifer Aniston about flair at restaurants

Fox

But only when she’s at a “certain type” of establishment.

Replay gallery

8 things you never knew about Office Space

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Office Space 20 years later

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Fox wanted Mike Judge to pursue Matt Damon and Ben Affleck as stars

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The studio asked Ron Livingston to fast before his screen test

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Jennifer Aniston and David Herman went to high school together

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Owen Wilson, Vince Vaughn, and Kate Hudson all auditioned for roles

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The "flair" storyline was added at the last minute

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Jim Carrey and Chris Rock were some of the movie's earliest fans

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Madonna had the hots for Michael Bolton

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To this day, people still ask Jennifer Aniston about flair at restaurants

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8 things you never knew about Office Space

1 of 10

Office Space 20 years later

1 of 10

2 of 10

Fox wanted Mike Judge to pursue Matt Damon and Ben Affleck as stars

2 of 10

3 of 10

The studio asked Ron Livingston to fast before his screen test

3 of 10

4 of 10

Jennifer Aniston and David Herman went to high school together

4 of 10

5 of 10

Owen Wilson, Vince Vaughn, and Kate Hudson all auditioned for roles

5 of 10

6 of 10

The "flair" storyline was added at the last minute

6 of 10

7 of 10

Jim Carrey and Chris Rock were some of the movie's earliest fans

7 of 10

8 of 10

Madonna had the hots for Michael Bolton

8 of 10

9 of 10

To this day, people still ask Jennifer Aniston about flair at restaurants

9 of 10

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