Owen Wilson names the single most important moment of his career: “Definitely the luckiest”
Unless you are a nepo baby, getting ahead in Hollywood requires a certain amount of luck. Talent, work ethic, and relentlessness all help, but without being graced with a hint of good fortune, you will be doomed to give up on your dreams or die while pursuing them, hopefully of old age.
Either you give the best audition of your life on the day that Martin Scorsese just happens to be attending casting sessions, or the right producer just happens to see your three-second scene in a TV movie while recuperating from back surgery. Maybe you’ve been doing bit parts for decades and finally get offered the script of a lifetime just because the top seven choices turned it down. Whatever the circumstances, being in the right place at the right time can only happen to a tiny fraction of Hollywood hopefuls.
Owen Wilson is no stranger to this reality. In fact, he’s more than happy to admit that his career is one of the prime examples. In the late 1980s, he was just a high school dropout fresh out of military school when he landed at the University of Texas. While there, he was roommates with an aspiring filmmaker named Wes, who eventually cast him in his first film, a 13-minute short called Bottle Rocket.
You might think that the universe throwing him into a bedroom with Wes Anderson would be the lucky break that Wilson remembers, but that distinction lies with another filmmaker: James L Brooks. When Anderson and Wilson made Bottle Rocket, Brooks had already attained legend status, having co-created The Mary Tyler Moore Show and The Simpsons, and directed, written, and produced Terms of Endearment and Broadcast News.
Brooks happened to see Bottle Rocket at the Sundance Film Festival and was so taken with it that he requested to meet the duo. He went all the way to Dallas for the occasion, listened to their read-through of the script, and then took them out to dinner. In the end, he agreed to produce a feature-length version of the film and became their mentor along the way.
“That was definitely the luckiest, most important thing that happened to me,” Wilson said in a 2016 conversation with Interview Magazine, recalling how invaluable it was to receive guidance from such an industry luminary. You could argue that luck wasn’t the only factor in that encounter.
The short film had been good enough to be accepted by Sundance after all, and Brooks had loved it so much that he’d gone out of his way to meet the people responsible for it. Decades later, however, Wilson is still convinced that it was luck rather than merit that made it happen.
The second lucky break that Wilson identified was meeting Ben Stiller. At that point, the Bottle Rocket star was out auditioning for roles, and the only one he managed to get was a minor one in Stiller’s 1996 film The Cable Guy.
Although that gig didn’t showcase his skills nearly as thoroughly as Bottle Rocket, it did lead to a long and intermittently fruitful collaboration with Stiller. It seems as though these two would have been brought together through some form of magnetic attraction at some point, but it just so happened that the bizarre Jim Carrey horror comedy was the moment.
