Last year, Owen Wilson made a comeback in a big way with his role as jet ski-loving TVA bureaucrat Mobius M. Mobius in the MCU’s Loki series on Disney+. Over the years, Wilson has been a frequent collaborator of revered comedy director Ben Stiller and revered tragicomedy director Wes Anderson. He’s an immensely likable performer, but some of his characters are more likable than others.
Unlike a lot of comedic actors, Wilson has never been boxed in by a particular type. He’s played all kinds of characters, ranging from wannabe career criminal Dignan in Bottle Rocket to womanizing wedding crasher John Beckwith in Wedding Crashers to the titular nightmarish houseguest in You, Me, and Dupree.
Eli Cash (The Royal Tenenbaums)
Wilson has one of the most important roles outside the titular family in Wes Anderson’s classic ensemble comedy The Royal Tenenbaums. Eli Cash is practically the unofficial fourth Tenenbaum child. He grew up across the street from them and became a staple at their family functions.
Eli is just as flawed as any of the Tenenbaums. He has an affair with Margot despite knowing that his best friend Richie (her brother by adoption) is in love with her. While high on mescaline, Eli recklessly crashes his car into the Tenenbaum house, narrowly missing Ari and Uzi and killing their dog, Buckley.
John Beckwith (Wedding Crashers)
One of the biggest box office hits of Wilson’s career, Wedding Crashers, paired him up with Vince Vaughn. They play a couple of carefree bachelors, John and Jeremy, who spend their free time crashing weddings to hook up with women.
Wilson’s character, John, isn’t as brash and chauvinistic as his buddy, Jeremy, played by Vaughn, but he’s still pretty sleazy. Throughout the movie, John starts to see the error of his ways after falling in love at a wedding he crashed
Detective Ken Hutchinson (Starsky & Hutch)
In one of his many collaborations with Ben Stiller, Wilson starred as one of the titular detectives in Todd Phillips’ self-aware movie adaptation of the classic TV show Starsky & Hutch. Wilson’s Ken “Hutch” Hutchinson is the wildcard of the “buddy cop” dynamic.
Hutch will happily bend the law in order to catch his perp. He’s a stark contrast to Stiller’s steadfast rule-follower David Starsky.
Francis Whitman (The Darjeeling Limited)
Francis Whitman, Wilson’s character in the underappreciated Wes Anderson comedy The Darjeeling Limited, is the oldest of three brothers on a soul-searching train journey across India. Francis is ridiculously controlling with his younger siblings. He orders for them in restaurants and plans the whole trip without their input. He even keeps hold of their passports so they can’t fly home early.
Throughout the movie, Francis gradually grows to trust his brothers to make their own decisions. He becomes more vulnerable and therefore more endearing when he confesses that his near-fatal motorcycle crash was a suicide attempt, not an accident.
Randolph Dupree (You, Me, And Dupree)
The title character in You, Me, and Dupree is a carefree slacker who moves in with his best friend and his new bride right after their honeymoon. Randolph Dupree quickly proves to be the houseguest from hell. He orders premium cable channels without permission, he makes their bathroom uninhabitable, and he’s caught red-handed having sex in the living room. Shortly thereafter, the candles he lit to set a mood start a fire that burns down the ground floor of the house.
Dupree might be a nightmare to live with, but he’s far from an unlikable character. He’s redeemed by his friendliness, sensitivity, and childlike innocence.
Hansel (Zoolander)
Ben Stiller’s sharp satire of the vapid world of modeling, Zoolander, stars Stiller himself as male model Derek Zoolander and Wilson as his closest rival Hansel. In fashion mogul Mugatu’s words, Hansel is “so hot right now.”
In the first half of the movie, audiences root against Hansel, because they’re following Zoolander, and Hansel threatens his career. But Hansel becomes more likable when he joins forces with Zoolander against a common enemy.
Lightning McQueen (Cars)
In Pixar’s Cars franchise, Wilson provides the voice of hotshot racer Lightning McQueen. Lightning is a cocksure, self-obsessed celebrity who’s humbled when he’s taken out of his fame bubble and stranded in a small town.
Being stuck in Radiator Springs and doing community service is exactly what Lightning needed. Getting out of his comfort zone and helping others makes him a better person.
Dignan (Bottle Rocket)
Both Wilson and Wes Anderson got their big break with Bottle Rocket. Anderson directed, Wilson starred as Dignan, and they both co-wrote the screenplay. Dignan is a wannabe career criminal with a 50-year plan to become rich from a series of daring heists.
Dignan’s penchant for theft would make him unsympathetic if he was better at it, but his hopelessness as a criminal mastermind makes him lovable. And he ultimately allows himself to be arrested to save his friends from a life behind bars.
Gil Pender (Midnight In Paris)
Wilson plays a West Coast Woody Allen stand-in in the fantastical romantic comedy Midnight in Paris. Gil Pender is a nostalgic writer who, during a trip to the French capital, discovers an ability to travel back to the Roaring Twenties and rub shoulders with his literary heroes, from Ernest Hemingway to F. Scott Fitzgerald.
During his trips to the past, the engaged Gil falls in love with another woman. This would make him unlikable, but his fiancée turns out to have been having an affair of her own long before that.
Ned Plimpton (The Life Aquatic With Steve Zissou)
Upon its release, The Life Aquatic with Steve Zissou received the most mixed reviews of Wes Anderson’s career. But it’s since been re-evaluated as a misunderstood masterpiece. Bill Murray plays the eponymous eccentric oceanographer (a satirical portrait of Jacques Cousteau), while Wilson co-stars as his long-lost son, Ned Plimpton.
While Steve has a laundry list of character flaws, Ned is just delightful. He’s kind to everybody and springs into action whenever danger is afoot.
