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To those who didn't know, teen heartthrob and turn-of-the-century film star Freddie Prinze, Jr. might seem like one of the last people they'd expect to work for a company like WWE. The She's All That and I Know What You Did Last Summer actor had a successful enough run in Hollywood, remaining fairly visible in the public eye through the 2000s.

RELATED: Freddie Prinze Jr. As A WWE Writer & 9 Other Celebs With Odd Wrestling ConnectionsHowever, what Prinze had (and, as evidenced by his current podcast Wrestling With Freddie, still has) is a love for professional wrestling. When a chance meeting with Stephanie McMahon while attending WrestleMania as a (well-connected) fan led to an in-depth discussion about the company's television product, the Billion Dollar Princess was so impressed that she encouraged Prinze to speak to her father, leading to the unlikeliest of working relationships.

Freddie Prinze Jr. Meets With Stephanie McMahon

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On his podcast, Prinze - who was born in 1976 and thus would've been part of Hulkamania's target demographic in the mid-1980s - said that he and friend Macaulay Culkin were in Orlando for the Hall of Fame ceremony on the night before WrestleMania 24. After extensive conversations with an unnamed WWE employee through the following day's Granddaddy of Them All, the "nice lady" said she thought Prinze had some "really cool ideas" and suggested he speak with Stephanie.

Prinze and his wife - Scooby-Doo co-star and Buffy the Vampire Slayer protagonist Sarah-Michelle Gellar - were already living in New York, so it was easy to take a train to Stamford, Connecticut to meet Stephanie at WWE headquarters. McMahon was receptive to his ideas, Prinze said, and much of their conversation was brainstorming ideas for struggling and stale talents. He said that Steph was particularly impressed that he had "notes on the brand" without "crapping all over it," and suggested he meet her father.

Freddie Prinze Jr. Becomes A Part Of WWE's Creative Team

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Prinze, whose father and 1970s Chico and the Man television star died when he was less than a year old, said that Vince called him "son" multiple times during their conversation. That, along with an old-school handshake, sealed the deal before Prinze could even tell his wife.

Opting to take his entire salary in company stock, Prinze said that he was feeling "disenfranchised" by his Hollywood career and perhaps saw working for WWE as a way out. Either way, he was soon flying to every live Monday Night Raw and Tuesday SmackDown taping, spending the rest of his time at the company's Titan Towers offices with folks like then-creative head Michael Hayes and Brian Gewirtz.

Burn Out Led To Freddie Prinze Jr. Quitting WWE

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With Vince McMahon's workaholic tendencies well-documented, it's no surprise that he expects his employees (particularly his office staff) to work the same long and grueling hours that he does, matching his near-constant availability. After two stints - first as a member of the creative team through early 2009 before being rehired as a producer and director from 2010 through 2012 - on the staff, a moment while watching the filming of an episode of Tough Enough made the young father reassess his career choice.

RELATED: 10 Wrestlers Who Had Children In The Past YearAs host Steve Austin was interviewing contestants, one woman said that she was trying out as a way to help her kids. Austin replied by informing her of the grim reality of parenthood while on the road full-time as a professional wrestler. Prinze said this moment resonated with him so deeply that while the show was still in progress, he approached Vince at the Gorilla Position and gave the company head his two weeks' notice directly.

Freddie Prinze Jr. Isn't Done With Wrestling

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Despite WWE's attempts at changing his mind, Prinze says that leaving the company was a no-brainer. "When I was able to give 100% and not focus on family, friends, or anything else, I was really, really good," he said on his podcast. "When I wasn’t able to do that, [the quality of his work] just wasn’t where it deserved to be.”

However, while Prinze - who only appeared on-camera a handful of times during his time in WWE - says he'll never consider going back, he's not done with the industry as a whole. In addition to his podcast, which he launched in November 2021, Prinze plans to open a promotion in California, where he says he's begun serious discussions about purchasing studio space for filming. However, he calls it a "three-year plan," and that his kids will always come first, saying "I love being a dad, it’s the reason I walked away from the business in the first place.”