One Of Owen Wilson's Best Roles Almost Went To Jake Gyllenhaal

Hollywood is bursting with "what if" scenarios — "Sliding Doors" moments where actors, writers, directors, and craftspeople almost made a certain project, or almost walked away from a job that would become huge for their careers. With the benefit of hindsight, these situations are often fun to think about — especially if, as in the case in today's example, A) the two people competing for a part were vying for a memorable role in a well-known movie, and B) they both went on to have great careers, so the thought exercise doesn't feel mean-spirited or just plain sad.

In an oral history of "Zoolander" published by Vanity Fair in 2021, "Zoolander" writer, producer, director, and star Ben Stiller explained how Owen Wilson nearly didn't end up playing Hansel, Derek Zoolander's rival-male-model-turned-friend, and identified the surprising actor who almost took the role instead:

"We wrote Hansel for Owen Wilson. But at a certain point, there was a question of whether or not he was going to do it. And I don't know if it was whether or not Owen wanted to do it, or if he was going to be available to do it. Because I definitely remember us doing readings for Hansel. And the one reading I remember being really funny — and he came in with like, a whole character — was Jake Gyllenhaal. But then Owen wound up doing it."

Having previously appeared together in "The Cable Guy," "Permanent Midnight," and "Meet the Parents" together, it's clear Wilson and Stiller had developed a strong working relationship and friendship that continued into working on "The Royal Tenenbaums," "Starsky and Hutch," and the "Night at the Museum" films. Owen Wilson was the perfect choice for Hansel, and he put such a distinctive stamp on that part that it's now difficult to picture any other performer inhabiting that character. But the notion that Jake Gyllenhaal, a guy who came very close to playing Spider-Man just a few years later, could have been mixing it up with Stiller as Hansel in "Zoolander" is a terrific "what if" to ponder. (Also fun to think about? The idea of Derek Zoolander getting hit by a train and dying in the closing minutes of the movie, something that was legitimately pitched at the time.)

Gyllenhaal is known for his committed dramatic performances; for me, 2014's "Nightcrawler" may represent the best work of his career so far. But the Oscar-nominated, drama-loving darker side of the actor tends to overshadow the lighter, goofier side of his personality in the public's imagination. This is the same person who popped up in a Lonely Island digital short on "SNL," appeared in a sketch on "Inside Amy Schumer," played the unforgettably deranged Mr. Music in "John Mulaney and the Sack Lunch Bunch," and slipped into a Scooby-Doo sketch in the most recent episode of "SNL." Could he have technically pulled off the ridiculous antics of Hansel? Absolutely.

More to the point, he also appeared in the unfortunate comedy "Bubble Boy" the same year that "Zoolander" came out, and folks who remember that movie (sorry to all of you) will now have a good idea of how old Gyllenhaal was when these discussions were taking place. When "Zoolander" hit theaters, Ben Stiller was 35 years old, Owen Wilson was 34, but Gyllenhaal was only 20. 

2001 was the same year that Richard Kelly's "Donnie Darko" came out, which became Gyllenhaal's calling card for years (though he almost missed out on that role, too). A case could be made that a Donnie Darko-aged Hansel who was much younger than Derek Zoolander could have worked for the "Zoolander" story, with the divide between old-school Derek and new-school Hansel becoming even sharper and potentially giving the film more opportunities to sneak in genuine commentary about obsession with youth in the entertainment and modeling industries. But thinking about how that casting might have altered the trajectory of Gyllenhaal and Wilson's careers, I'm personally glad things shook out the way they did.