5 Best Owen Wilson Roles

5 Best Owen Wilson Roles

By all accounts, Owen Wilson is one of the nicest guys in Hollywood. He’s also one of the hardest-working. With a career that spans decades, it would be easy for Wilson to rest on his laurels and appear in comedy after comedy, showing little depth and even less talent. But Wilson doesn’t do that. For every comedy he puts out (and, to be fair, they’re usually pretty funny), he’ll challenge himself with roles in films like Midnight in Paris or Wonder.

With his trademark crooked nose, golden locks and favorite saying (“Wow), Owen Wilson has captured the hearts of audiences worldwide. He has appeared in comedies, dramas, horror films and more. He’s teamed with Jackie Chan, Vince Vaughn, Ben Stiller and more. Wilson has left an indelible mark on Hollywood, both with his talents as an actor and with his integrity as a man. To see Owen Wilson is to smile. His own smile is infectious and he brightens up any movie that he is in. Except Anaconda. That sh*t’s dark. These are the 5 Best Owen Wilson Roles.

5) Hansel – Zoolander (2001)

5 Best Owen Wilson Roles

That Hansel is so hot right now. When Owen Wilson was cast in the Ben Stiller film, Zoolander, we weren’t quite sure what to make of him. Wilson played a male model named Hansel, who was the rival-turned-accomplice of Stiller’s Derek Zoolander. He was aloof but good-natured and, as alluded to, so hot. Zoolander was a weird, quirky comedy that somehow became a classic thanks, in large part, to the chemistry between Wilson and Stiller. They would team up in other films, but it was Zoolander that highlighted their relationship the best. Zoolander 2, on the other hand? So, not hot.

4) John Beckwith – Wedding Crashers (2005)

5 Best Owen Wilson Roles

In a film worshiped by boisterous bachelors everywhere, Wilson starred as John Beckwith in Wedding Crashers. Alongside Vince Vaughn, Wilson portrayed a young, single man who goes to weddings he wasn’t invited to with his best friend Jeremy (Vaughn) to pick up women. But, to be fair to John and Jeremy, they’re not just looking to meet women. They also enjoy the food, music and camaraderie that comes with weddings. For years, John and Jeremy have planned their whole seasons based on weddings, but they never expected to fall in love. That’s actually what happens when they meet Claire and Gloria Cleary, two sisters with vastly different ideas about love, sex and commitment.

The chemistry between Wilson, Vaughn, Rachel McAdams and Isla Fisher is tangible. Wedding Crashers is the perfect movie to watch before or after witnessing the holy matrimony of strangers. We don’t recommend crashing any weddings but, if you do, do it with the same style and grace as Owen Wilson.

3) Nate – Wonder (2017)

5 Best Owen Wilson Roles

Proving that there’s more to him than just laughs, Owen Wilson likes to find himself in dramatic roles from time to time. One of those roles was as Nate, the father of a young boy named Auggie who has a facial deformity and is understandably nervous about going to a mainstream elementary school for the first time. The real star of Wonder is Jacob Tremblay, the boy who played Auggie, but Wilson does a phenomenal job as Auggie’s dad. He never takes away from Tremblay’s performance, but he offers up one himself that any parent can find relatable. Nate loves his son and doesn’t want him to get hurt, but he also wants him to try to live as normally as possible. He’s conflicted and it’s a performance that Wilson absolutely did not take lightly.

Usually, Owen Wilson’s films are meant to make you laugh. Wonder challenges you not to.

2) Matty – How Do You Know (2010)

5 Best Owen Wilson Roles

How do you know when you’re in love? That’s the question posed by Owen Wilson’s character Matty in the 2010 film How Do You Know, directed by James L. Brooks. How Do You Know is a film about a love triangle between Lisa (Reese Witherspoon), George (Paul Rudd) and Matty. Matty and George are vastly different but both are charming in their own quirky ways. As Lisa faces tough decisions in her personal and professional life, she continues to find herself drawn to George, despite her relationship with Matty.

Wilson is a side-character in this film but he makes what could be an extremely unlikable character into somebody that at least part of us is hoping gets a happy ending. Matty selfish, full of himself and completely out of touch with reality, but he’s still just so damn likable, all in Wilson’s performance.

1) Gil Pender – Midnight in Paris (2011)

5 Best Owen Wilson Roles

There is one performance that sets Wilson apart from all of his contemporaries though, and that is his role as Gil Pender in the 2011 film Midnight in Paris. From the mind of Woody Allen, Midnight in Paris tells the story of a romantic-at-heart named Gil who is on holiday in Paris with his girlfriend and her parents. While the girlfriend and her parents don’t share Gil’s excitement for the City of Lights, Pender ends up meeting various historical figures from Paris’ illustrious past.

Gil is a writer and, when he finds himself outside of a church at midnight, he is transported to Paris in the 20’s. While there, Gil meets Hemingway, Fitzgerald, Picasso, Gertrude Stein and more. All of them prove to Gil that magic really does happen in Paris. But they also show him that you don’t need to wax nostalgic for the former history of Paris- you can make that magic yourself.

Midnight in Paris is, without question, Owen Wilson’s best movie. A big reason for this is the magic that he, himself, brings to every role he takes on.