Jake Gyllenhaal Was Almost Cast as Owen Wilson's Character in Zoolander

Jake Gyllenhaal nearly starred opposite Ben Stiller in the beloved comedy Zoolander, but Owen Wilson ultimately took on the role of Hansel.

By Cydney Contreras Sep 29, 2021 1:29 AMTags
Watch: "Zoolander" Turns 20: Live From E! Rewind

Sure, Jake Gyllenhaal may be really, really, ridiculously good looking, but it seems that even his charm and good looks couldn't land him the role of Hansel in Zoolander.

Ben Stiller recently spoke to Esquire about making the film, which turns 20 years old this year, revealing that Owen Wilson was always his first pick to play Hansel. But they had to have a backup star in case Owen's schedule prevented him from taking on the role.

This is where Jake comes into the picture. According to Ben, he was one of the many actors who auditioned to play Hansel, who is Derek Zoolander's rival-turned-ally. 

Ben shared, "The only one that I remember clearly was a young Jake Gyllenhaal doing this wide-eyed version of Hansel that was really funny."

Ultimately, Owen's schedule cleared up, allowing the Wedding Crashers actor to star in the now-iconic comedy.

Jake Gyllenhaal's Many Viral Moments

Another star that nearly nabbed a role in the film was Andy Dick, who Ben imagined playing Mugatu. Will Ferrell ended up portraying the villain, with Stiller saying, "Now it's impossible for me to picture anybody but Will doing it."

Wilson Webb/Scott Rudin Prods/Paramount/Kobal/Shutterstock

This isn't the first time Jake has been passed over for a role. He previously auditioned for Peter Jackson's Lord of the Rings, but was told that his British accent wasn't up to par. 

"I really do remember Peter Jackson saying to me, 'You know that you have to do this in a British accent?'" he told The Hollywood Reporter in 2013. "We heard back it was literally one of the worst auditions."

He was also a strong contender to play the lead in Baz Luhrmann's Moulin Rouge, but they went with Ewan McGregor on account of his age. And it was ultimately for the best, as it marked the beginning of his friendship with Heath Ledger

Universal Studios

Jake recalled that pivotal moment in a 2018 interview with GQ, sharing, "When Ewan was cast, I finally met Heath and we sort of became friends before Brokeback Mountain based on our mutual frustration. When Brokeback Mountain came out and it got all the attention it did, I remember, a few months later, Heath called me and he was like, ‘Hey mate, I got some news for you.'"

"I said, ‘What?'" Jake continued. "He said, ‘Baz just offered me his next movie. I just wanted you to know, I f--king turned it down!' So that was how much Heath loved me, you know. That was how I met him."

In other words, everything happens for a reason.

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