Owen Wilson has been collaborating with Wes Anderson since the very beginning of both of their careers. The script for Bottle Rocket, the delightful indie crime caper that made Wilson a star and marked Anderson’s directorial debut, was co-written by the actor-filmmaker pairing. Wilson went on to co-write Anderson’s next two movies, Rushmore and The Royal Tenenbaums.

Out of Anderson’s 10 feature films, Wilson has appeared in seven of them. Sometimes, he has a lead role with his name above the title; other times, he plays a scene-stealing supporting role. From Dignan to Eli Cash to Ned Plimpton, Wilson has played plenty of memorable roles in Anderson’s filmography.

7 Herbsaint Salzerac (The French Dispatch)

In Anderson’s latest movie, The French Dispatch, Wilson plays Herbsaint Salzerac, the travel writer for the titular magazine. He’s only featured for a few minutes near the beginning of the movie as he shows the audience around the fictional town of Ennui in a charming, meticulously staged montage.

It’s Wilson’s job to establish the quirky milieu of the movie, and he looks extremely stylish wearing a beret and riding a bicycle. Unfortunately, his appearance in The French Dispatch is too brief to be all that memorable. Jeffrey Wright’s Roebuck Wright, Timothée Chalamet’s Zeffirelli, and even Bill Murray’s Arthur Howitzer, Jr., who has a similarly limited role, make more of an impression.

6 M. Chuck (The Grand Budapest Hotel)

Wilson doesn’t show up until near the end of The Grand Budapest Hotel, playing M. Chuck, M. Gustave’s temporary replacement while he’s in prison. M. Chuck is a typical Wilson character: warm, friendly, likable. His job performance as the concierge of the Grand Budapest isn’t quite as spotless or articulate as M. Gustave, but it’s close.

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Along with Edward Norton’s military police character, M. Chuck is the deadpan “straight man” opposite the slapstick antics of the movie’s gun-toting finale.

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5 Coach Skip (Fantastic Mr. Fox)

In Anderson’s first foray into stop-motion animation, Fantastic Mr. Fox, Wilson voices Ash Fox’s gym teacher, Coach Skip. He gets a hysterical monologue explaining the ridiculous rules of “Whack-Bat.” Coach Skip is a relatively minor role in Fantastic Mr. Fox – George Clooney and Meryl Streep lead the movie in the roles of Mr. and Mrs. Fox – but he’s certainly memorable, largely thanks to having Wilson’s unmistakable voice.

Coach Skip isn’t a brash, loudmouthed jock like most gym teachers in movies and TV shows. In fact, he’s the total opposite. Like most Wilson characters, he’s hilariously mild-mannered.

4 Eli Cash (The Royal Tenenbaums)

Eli Cash isn’t a member of the titular family in The Royal Tenenbaums – he’s just a long-time family friend – but he desperately wants to be a Tenenbaum. He becomes a popular western author almost by accident with an alternate history novel called Old Custer. He has a fun dynamic with a bunch of other characters: an endearing lifelong friendship with Richie, a strained love affair with Margot, and he’s oblivious to Royal’s hatred of him.

Wilson plays Eli as human and vulnerable, caught in the throes of addiction. He’s involved in one of the funniest sequences in the movie when, high on mescaline, he crashes into the Tenenbaum residence, narrowly avoiding Chas’ kids, and the overcautious Chas loses it and chases him through the house.

3 Francis Whitman (The Darjeeling Limited)

Arguably Anderson’s most underrated movie, The Darjeeling Limited masterfully captures the difficulties with communication between brothers. Wilson stars as Francis Whitman alongside Jason Schwartzman and Adrien Brody as his younger brothers Jack and Peter, respectively.

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The painfully relatable Francis is absurdly controlling without realizing it. He orders for his brothers in restaurants and he’s constantly saying, “Let’s make an agreement,” and “Can we agree on that?” Throughout the movie, he’s recovering from a motorcycle accident that’s poignantly revealed to be a suicide attempt when the brothers reunite with their estranged mother.

2 Ned Plimpton (The Life Aquatic With Steve Zissou)

The heart of The Life Aquatic with Steve Zissou is Steve’s long-lost son’s desperate attempts to connect with him. Ned Plimpton, a Kentucky pilot who joins Team Zissou to get closer to his estranged dad, is Wilson’s most wholesome, likable character in the Anderson oeuvre. Sadly, he’s also the one who meets the most sudden and heartbreaking end.

It’s hard not to choke up during Ned’s burial at sea. It would’ve been a tragedy if any of the characters in The Life Aquatic died, but Ned was nothing but generous and caring from the moment he was introduced.

1 Dignan (Bottle Rocket)

The first role that Wilson played in an Anderson movie was also the first role that he played in any movie. Luke Wilson is the real star of Bottle Rocket, playing the put-upon everyman who’s roped into his friend’s zany get-rich-quick scheme, but his brother gives a fantastic performance as that friend. As a wannabe criminal whose dimwittedness becomes his downfall, Dignan is extremely lovable.

He wants to become a career thief, but he’s so hilariously inept at it that it’s impossible not to root for him. In the disastrous final heist, Dignan proves himself to be a good guy when he takes the fall to allow his friends to escape.

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