The Iconic Zoolander Role Jake Gyllenhaal Almost Played

Over the years, plenty of casting choices that never came to fruition have leaked, primarily through candid interviews, leading us to ponder what could've been. Had film history gone in a different direction, we may have seen Miles Teller as a young Han Solo in the Star Wars spinoff or Michelle Pfeiffer may have taken Jodie Foster's role in "The Silence of the Lambs" (via Insider). Wild, right? 

Well, we can add another surprising casting "What if?" to this growing category. It appears Jake Gyllenhaal was, at one point, close to getting a role in the 2001 comedy "Zoolander." Starring Ben Stiller as the adorably dumb male model Derek Zoolander, this '00s hit boasts a solid cast, including Owen Wilson, Will Ferrell, Jon Voight, Christine Taylor, Milla Jovovich, and Alexander Skarsgård. Which role did Gyllenhaal audition to play? Well, it turns out that he went up for a role that is now so iconic the thought of it almost going to the "Donnie Darko" actor is fascinating to consider.

Ben Stiller spoke to Esquire to celebrate the film's 20th anniversary. While chatting with the magazine, the director, writer, and star of "Zoolander" shared trivia about the making of the movie. One jaw-dropping detail was that, while Owen Wilson was the original choice for Derek Zoolander's foe-turned-friend Hansel, another actor was considered that would've put the character in a very different light.

According to Stiller, Wilson was, at one point, unavailable at the time "Zoolander" was scheduled to film. Stiller had no choice but to have auditions for Hansel, the gorgeous blond model Wilson ended up playing. Enter Jake Gyllenhaal. The "Zoolander" director recalled, "The only one that I remember clearly was a young Jake Gyllenhaal doing this wide-eyed version of Hansel that was really funny." He wasn't the only maybe on the list either, as Stiller revealed that Zoolander's massive-haired foe, Mugatu, could have been played by Andy Dick. Scheduling conflicts meant this didn't come to pass, and the role went to Will Ferrell. Stiller admits, though, that it paid off: "Now it's impossible for me to picture anybody but Will doing it."

It'd be interesting to see what Gyllenhaal could've brought to the part of Hansel. While some of his previous roles have displayed comedic elements, a film like "Zoolander" doesn't appear in his IMDb profile (besides the absolute classic "Bubble Boy," of course). For now, we can only wonder what a walk-off between Gyllenhaal's Hansel and Stiller's Zoolander would have looked like.