How 'Office Space' Star Ron Livingston Beat Out Matt Damon for the Job and Co-Star Jennifer Aniston Had Crush on in High School

And Jennifer Aniston reveals she was “madly in love” with one of her co-stars in high school as cast and crew celebrate 20th anniversary of cult comedy.

Can you imagine "Office Space" with Matt Damon in the lead role? It almost happened.

Entertainment Weekly gathered writer-director Mike Judge with the cast and crew to spill behind-the-scene secrets in honor of the cult comedy’s 20th anniversary, and they dropped more than a few fun anecdotes. Our favorites, however, boiled down to the story of how Ron Livingston beat out the "Good Will Hunting" star for the role of Peter, and Jennifer Aniston being "madly in love" with one of the actors in high school. We’ll get to that in a minute, but we would have never guessed who it was based on the actress’ dating history.

Judge explained that when 20th Century Fox gave the 1998 comedy the greenlight, executives wanted him to consider casting Damon as the insecure Initech programmer who accidentally achieves a permanent state of relaxation after a hypnotherapy session goes awry. "They didn’t like the actors I wanted. I came close to backing out," Judge revealed, but he was game to give Damon a shot.

Casting director Nancy Klopper said, "Mike agreed to go to New York and meet with Matt, who was a fan of his. Then Ron Livingston’s agent asked if he could audition. He’d been in ‘Swingers’ and a few TV comedies, but wasn’t well-known."

Livingston’s part in "Swingers" was small, so he credited leads Vince Vaughn and Jon Favreau’s fame as the reason he was even given a shot. Judge wasn’t in the room when Livingston auditioned, but those who were there were stunned: he knocked it out of the park.

"Mike writes in a very specific cadence," Klopper explained. "When Ron read I was like, ‘Oh my God. I was knocked out."

Livingston added, "I did a damn good audition. I commandeered Nancy’s desk and started using her drawers, files and phone."

So Klopper sent the tape to Judge in New York immediately with the message, "You’re not going to believe this guy."

Judge said he asked the hotel for a VHS player (remember those!?), then called the casting director back immediately after watching Livingston’s audition and said, "I could make this movie today with Ron."

So what about Damon? Judge explained, "I met with Matt, who was really nice and liked the script. But I’d found Peter."

Aniston was also on hand for the nostalgic chat, and dropped a "fun fact" that she went to high school with "Office Space" star David Herman, who memorably played Peter’s fellow disgruntled employee Michael Bolton alongside Ajay Naidu’s Samir. The trio is most famous for beating the hell out of a printer in slow motion.

The A-list star who has been married to Brad Pitt and Justin Theroux revealed she actually had a huge crush on Herman when she was a teenager.

"Fun fact: I’d gone to high school in New York with David Herman. I was a sophomore when he was a senior. He was a quiet, genius actor-type back then. I was sort of madly in love with him, and also terrified of him," she said with a laugh.

Herman revealed another fun fact. "Thanks to her star power, a bunch of unknowns were in the movie. Would never happen today," he said, referencing the fact that Aniston was a bonafide TV star at the time because of "Friends."

Klopper said that studio demanded a "big name" for Joanna, the waitress character Aniston played, since the male lead was relatively unknown.

Producer Michael Rotenberg added that Aniston "loved the script, but there was concern about having such a big star in a smaller role."

"I don’t think I was the biggest anything at the time," Aniston said. "I was excited about doing a comedy like ‘Office Space’; features like that weren’t flying my way at that point."

Livingston joked, "Jen’s agents probably told her she was going to co-star with Matt Damon."

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