For more than a quarter-century, Owen Wilson has been one of the most prolific and hilarious actors in Hollywood, turning out one hit comedy after another in a variety of different subgenres. Whether it’s iconic 2000s comedies alongside the likes of Ben Stiller and Vince Vaughn, more action-centric roles with the living legend Jackie Chan, or more fantastical affairs that blend comedy, romance and the power of imagination, Wilson has done a little bit of everything over the years.
As we prepare for the release of PAINT, which will see the actor play a Vermont painter inspired by the life and career of the late Bob Ross in April 2023, we just couldn’t help but look back at some of the more memorable comedic Owen Wilson movies, and his roles that have withstood the test of time and continue to make us laugh all these years later.
John Beckwith - Wedding Crashers (2005)
Having a list of Wilson’s most memorable comedic roles and not starting with John Beckwith in WEDDING CRASHERS just doesn’t feel right. The unforgettable 2005 comedy about a pair of serial wedding crashers who get in way over their heads has become the stuff of legend in the 18 years since its release, and a lot of that is because of the performances by Wilson and co-star Vince Vaughn.
So much about these two, who were on top of the world at the time, just works, and the chemistry they share with each other, as well as with the rest of the cast, create a comedy pairing that led to the quintessential R-rated comedy of the early 2000s.
Gil Pender - Midnight In Paris (2011)
A lot of actors have played the “Woody Allen” character over the years, but few compare to Owen Wilson’s Gil Pender in the Academy Award®-winning filmmaker’s 2011 fantasy-comedy, MIDNIGHT IN PARIS. There is something magical about Wilson’s portrayal of the screenwriter and aspiring novelist obsessed with 1920s Paris, and the “Lost Generation,” that adds a certain charm to this unique and imaginative movie.
A different brand of comedy than some of Wilson’s more mainstream movies of the era, MIDNIGHT IN PARIS does feature some of his most hilarious interactions, especially whenever he is sharing the screen with Michael Sheen’s annoying and pedantic know-it-all, Paul Bates. Though, the fantastical nature of the time-traveling elements do lead to some humorous moments, especially with Adrien Brody’s Salvador Dali.
Hansel McDonald - Zoolander (2001)
Ben Stiller’s outlandish 2001 comedy, ZOOLANDER, which saw the writer-director-actor portray down-on-his-luck male model Derek Zoolander, is one of the most over-the-top comedies of its era, and for good reason. The plot, which centers around Zoolander becoming wrapped up in an assassination plot orchestrated by fashion mogul Jacobim Mugatu (Will Ferrell) before teaming up with former rival Hansel McDonald (Owen Wilson), is admittedly ridiculous, but creates comedy gold in the process.
More than 20 years later, it’s impossible to forget Wilson absolutely killing it with his introductory scene early on in the movie, his bonding moment with Zoolander and the legendary computer scene. It doesn’t get much better than this.
Kevin Rawley - Meet The Parents (2000)
A lot of the hilarious, and intense, moments in the 2000 comedy, MEET THE PARENTS, comes from the various interactions between Stiller and Robert De Niro’s characters, but Wilson does come off the bench midway through the movie to help move the story along in a great and understated way. Playing Stiller’s girlfriend’s ex, Kevin Rawley, Wilson comes in as the polar opposite of the star’s Greg Focker, and is completely charming in the process.
Though he’s not in the movie all that much, Kevin is involved in some great moments like the volleyball game, discussions about injured dogs, and the unforgettable backed-up septic tank scene that creates quite a messy, and stinky, situation.