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March 27, 2026
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Jake Gyllenhaal Was Almost Cast as Owen Wilson’s Character in Zoolander

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.

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