The Best Movie Ever | Best Owen Wilson Movies

Owen Wilson has an easy drawl and a cheerful personality, and it’s made him the ideal comedic foil for many comedians over the last 20 years, including Ben Stiller, Vince Vaughn, Eddie Murphy, Jack Black and Jackie Chan. But although most audiences know the actor as a lighthearted comic figure, his career also includes serious dramas, action thrillers and Oscar-nominated screenplays.

With Owen Wilson’s latest movieNo Escape, opening in theaters this week, bringing with it a reminder that Wilson has serious dramatic chops, we started wondering… What’s the best Owen Wilson movie ever? So we asked Crave’s critics – William Bibbiani, Witney Seibold and Brian Formo – to pick one film, just one, to represent the finest work of the actor’s career.

Best Owen Wilson Movies Ever

What follows, dear readers, is what they came up with as the best Owen Wilson movies ever. Check out what they selected, find out why, and be sure to come back next week for an all-new, highly debatable installment of Crave’s The Best Movie Ever!

William Bibbiani’s Pick: Bottle Rocket (1996) 

Columbia Pictures

Columbia Pictures

In some ways it just seems rude to say an actor’s first film was their very best. Maybe it’s a matter of perspective, and interpretation. Bottle Rocket was our first introduction to the talents of Owen Wilson, and introduced us to what would become his memorable on-screen persona. He was affable, funny, sincere, and a hopeless dreamer. Many of Owen Wilson’s best movie roles since Bottle Rocket have played like variations on the same themes, including Midnight in Paris (my runner up), so this film laid the groundwork, and quite successfully too.

The first feature film from Wes Anderson stars Owen and Luke Wilson as 20-something dreamers who embark on a life of crime, despite having no talent to speak of, no motive, and nothing really to steal. It’s their enthusiasm that matters. Owen Wilson plays Dignan, the mastermind of the pair, who has laid out their future for 20 years in a cheap notepad scribbled with details. He puts more effort into the idea of wearing tape across his nose during a heist (“Why is there tape on your nose?” “Exactly.”) than he does his own friendships. He is playing at confidence, playing at criminality, and ultimately playing anything he can to avoid becoming a real adult.

The laid back performances and droll little script (co-written by Owen Wilson and Wes Anderson) make Bottle Rocket feel like a lazy summer daydream, a fantasy that isn’t quite fantastic enough. And as such, Dignan becomes a valuable audience surrogate, representing our desires to be important and cool and stylish and our complete inability to do so because life doesn’t work like that, and all that really matters is who we’re with, and what we are currently doing. He is us, and he is dreaming, and that makes Dignan one of the most special characters in all of cinema, and easily the best Owen Wilson Movie of his career.

Brian Formo’s Pick: Rushmore (1998) 

Touchstone Pictures

Touchstone Pictures

Owen Wilson does appear in Rushmore, but only in a photo, so to call it his best film requires me to look at the differences in director Wes Anderson’s films written with Wilson as a co-scripter (Bottle Rocket, Rushmore, and The Royal Tenenbaums), and his films co-written with others (Moonrise Kingdom, The Grand Budapest Hotel, The Life Aquatic, The Fantastic Mr. Fox and The Darjeeling Limited). Using Anderson’s films as an intricate map, it appears that both Anderson and Wilson are big dreamers. But Anderson’s dreamers exist in rooms and palaces with imaginative pastels, letters, costumes, and soundtracks—his dreamers are often a product of this stimuli and otherwise detached. Whereas Wilson’s dreamers are underdogs who have to reshape themselves in the face of failure. While Anderson has made many great films, his ones with Wilson do share a more grounded story, and more despondent—but richer—characters. And Rushmore is the best. 

Max Fischer (Jason Schwartzman) is a young man who’s defined by his extracurricular activities in Rushmore, but his failures in schoolwork make him confront the blue collar roots that none of his private school ‘mates share. Max uses the school as his own personal playhouse, and activities’ revival room because his home life is so small. But failing at school obviously removes the ability to make his own personal dreams come true. On the opposite side, the kids of a local construction magnate (Bill Murray) get numerous chances—and so does their rich father. 

Wilson only appears in a photo in Rushmore, as a now-deceased husband to Rosemary (Olivia Williams), whom both Max and Murray pine for. Wilson’s photo serves as a reminder that life (and death) is what happens when you’re busy making plans. In Anderson’s previous film, Bottle Rocket, Wilson had one of the main roles, and played a young man who tried to easily plan out both his and best buddy’s entire life, free of pain. It didn’t pan out. As a collaborator though, Wilson appears to throw the life at Anderson’s bigger (pastel-filled) plans.

Witney Seibold’s Pick: The Minus Man (1999) 

Shooting Gallery

Shooting Gallery

Owen Wilson’s appeal as a performer comes in his ease. He has played uptight, tough, or energetic characters, of course, but his on-screen persona is always infused with Wilson’s own ineffable affability. He may be clueless or even mean in certain roles, but he always has a gentle confidence; a quality that assures audiences that, somewhere, there is a realm where this character is king. 

In 1999, when Wilson’s star was still on the rise, prolific ’60s TV actor Hampton Fancher, also a screenwriter on Blade Runner, directed his only feature, a bizarrely languid contemplation on violence called The Minus Man. The film was a gentle narration by Owen Wilson’s Vann, a kind, calm, and sensitive soul who drifts from town to town looking for odd jobs and offering advice. He even has the occasional almost-romance, as with the laconic Ferrin (Janeane Garofalo). Also, Vann is a serial killer who murders women, often on short impulse. 

This is not a film that glorifies its violence, and indeed keeps all its murders largely off-camera. This is not a twisted look at the blackened heart of the American male (see American Psycho for that). This is more a sad, almost regretful meditation on the way the hear operates, and how some people, no matter how warm, can still be complete sociopaths. As Vann, Wilson’s natural approachability is almost turned on ear. He’s not a smooth-talker or seducer or wicked incubus. He’s just a nice, friendly dude, safe in his cluelessness and good-heartedness. He’s also a slave to his impulses, and smart enough to elude capture. Is his friendliness an act, or is it convenient for his dark hobby? It’s definitely one of the best Owen Wilson movies ever.