The 10 best films starring Owen Wilson
(Credit: Sony Classics)

From Woody Allen to Wes Anderson: Owen Wilson’s 10 best films

Do I know what I’m doing today? No. But I’m here, and I’m gonna give it my best shot. – Owen Wilson

American actor Owen Wilson is one of the most established and recognisable faces working in the industry today. Renowned for his quirky and wonderfully weird outings in director Wes Anderson’s films, Wilson has enjoyed an immensely successful career in the movies that spans more than 25 years. Also known for his screenwriting abilities, Wilson earned an Academy Award nomination in 2002 for co-authoring The Royal Tenenbaums with Wes Anderson and the pair also scripted Bottle Rocket and Rushmore together. Still going strong, he continues his collaboration with Anderson in The French Dispatch, a film which is just around the corner.

Born and raised in Dallas, Wilson attended the University of Texas at Austin, where he roomed with Anderson and together they wrote the screenplay for Anderson’s first feature, Bottle Rocket. The actor’s and the director’s careers sort of mushroomed from there. “My roommate in college in Austin, Texas, was Wes Anderson,” he once commented. “Wes always wanted to be a director. I was an English major in college, and he got us to work on a screenplay together. And then, in working on the screenplay, he wanted my brother, Luke, and me to act in this thing.” Wilson adds: “We did a short film that was kind of a first act of what became Bottle Rocket.”

Post-Bottle Rocket, Wilson has enjoyed leading turns in films like Behind Enemy Lines, I Spy, Marley and Me, and Wedding Crashers. Wilson starred as a nostalgia-seized writer in Midnight in Paris, written and directed by Woody Allen. The film premiered at the 64th Cannes Film Festival to critical acclaim and earned him a Golden Globe Award for his performance.

Growing up only dreaming about working in the movies, Wilson admits that the acting aspect of it might come in accidentally. He explains: “It was something I didn’t know I would continue to do because it’s a little bit out of your hands—it just depends on how people react to you or if people want to hire you. Maybe that’s why there’s insecurity sometimes in acting because it’s not like there’s a correlation between hard work and how people receive you.”

“But after Bottle Rocket, I started getting acting work. People started offering me roles in movies. It wasn’t something that I thought about as a kid growing up in Texas. Actually, maybe I would have thought of it as a possibility, but it seemed so crazily far-fetched to think that you could work in movies that I really didn’t ever quite imagine it. It was just lucky.”

On the occasion of his 52nd birthday, we list the best ten films featuring Owen Wilson.

Owen Wilson’s best ten movies:

10. Shanghai Noon (Tom Dey – 2000)

The Old West meeting the Far Eat, this Jackie Chan-led martial arts-meets-Western comedy starred Owen Wilson as Roy O’Bannon, a rather inept outlaw who starts out hijacking Wang’s (Jackie Chan) train but ends up becoming an invaluable ally in his quest. Chan and Owen Wilson proved to be one of the more unlikely of effective buddy comedy duos, but that’s exactly what they are in Shanghai Noon.

The film, set in Nevada and other parts of the American West in the 19th century, is a juxtaposition of a Western with a kung fu action film with extended martial arts sequences, and also has hoards of comedy featuring two vastly different heroes (a Chinese imperial guard and a white Western outlaw) who team up to stop a crime.

Wilson recalls about playing his character in the film: “I try to find a way to make it comfortable or interesting or funny to me. I remember working with Jackie Chan on Shanghai Noon, and when we were working on the script, I thought that my character thought about being an outlaw the way a kid today would think about being a rock star, as a way to impress girls. So it was just kind of a funny idea, but once we had that idea, it changed the character and made it something that was funnier to me to play.”

9. Meet the Parents (Jay Roach – 2000)

Another hilarious comedy, Meet the Parents tells the story of Greg Focker (Ben Stiller), a male nurse from Chicago, visits his girlfriend’s Pam parents at Long Island. There he learns that his would-be father-in-law is a no-nonsense retired CIA agent (De Niro) who thinks Greg isn’t good enough for his little daughter. Greg tries to win his approval but things don’t go exactly as he expected. Owen Wilson stars as Kevin Rawley, the wealthy broker/carpenter ex-fiancé of Pam. He gives us a single “wowww” which is all it should take to convince you to watch this.

Meet the Parents went on to become one of the highest-grossing films of 2000 and was well received by film critics and viewers alike, winning several awards and earning additional nominations.

With Meet the Parents included, Wilson has starred alongside Ben Stiller in twelve movies. Talking about their relationship, he says: “In a way, it kind of doesn’t seem quite believable. Like, geez, have we been in Hollywood that long where we could have worked on these many movies together? It’s a little bit strange to think that we’ve worked together so much and we’ve been around so long that we could have.”

8. Marley & Me (David Frankel – 2008)

Marley & Me is a wonderful album of life; taking us through the ups and downs of it, the failed expectations and the sudden blessings. It is a story that affects all of us, both young and old. Based on the 2005 memoir of the same name by John Grogan, the film stars Owen Wilson and Jennifer Aniston as the owners of Marley, a Labrador retriever.

Admittedly, Wilson had great fun shooting opposite the canine co-stars: “Actually, I don’t remember it happening. Clyde was the main dog who played Marley and he was quite consistent about misbehaving and doing stuff. You’re sort of a little bit like the crew, the director, everyone’s like… I’d say my line and now: ‘Is [the dog] going to pick up that? Yes! He’s got it! Okay, I’ll say my other line now.’”

7. Wedding Crashers (David Dobkin – 2005)

David Dobkin’s sex-comedy Wedding Crashers starred an ensemble of Owen Wilson, Vince Vaughn, Christopher Walken, Rachel McAdams, Isla Fisher, Bradley Cooper, and Jane Seymour, and follows two divorce mediators (Wilson and Vaughn) who crash weddings in an attempt to meet and seduce women. One of the most successful films in Wilson’s filmography, the film grossed $288.5 million worldwide, receiving critical plaudits along the way. Amazingly, Wedding Crashers is credited with helping to revive the popularity of adult-oriented, R-rated comedies.

Would you be chuffed to bits if someone crashed your wedding? “Would I? It depends on the person. If some of the people seated next to me on this podium were to crash my wedding – and they would have to crash, they wouldn’t be invited – I’d probably let bygones be bygones and welcome them. I’d shake their hands so they could see that I’m not holding a dagger.”

6. Cars (John Lasseter – 2006)

In 2006, Wilson lent his vocal talent to Cars, an animated film about a racecar who learns the true meaning of friendship and family. Cars is far from Pixar’s best-received film, but it still grossed over $460 million at the box office, ranking number one in the US during its opening weekend with a $60 million gross. It also spawned a sequel and a spinoff, Planes. In the film, Wilson voices the racecar Lightning McQueen, as he embarks on his mission to win the Piston Cup from other challengers.

Cars garnered generally positive reviews and also received commercial success, grossing $462 million worldwide against a budget of $120 million. It was nominated for two Academy Awards including Best Animated Feature but lost to Happy Feet.

At a promotional event, Wilson revealed the secret behind his casting. “Yeah, there is some talk. Uh, I saw Jackie (Chan) not too long ago and we were talking about it. But, it’s funny that you mention that because Shanghai Noon was the movie, I think, that helped me sorta become involved with Cars because when I met John Lasseter, he and his kids had enjoyed that movie. And, he said that he had this animated movie that he thought maybe I’d be good for so that’s, you know, how I ended up getting cast as Lightning McQueen.”

5. Inherent Vice (Paul Thomas Anderson – 2014)

Paul Thomas Anderson’s period neo-noir crime film, based on the 2009 novel of the same name by Thomas Pynchon follows Larry “Doc” Sportello, a well-intentioned but inept stoner, hippie, and private investigator in 1970, who is embroiled in the Los Angeles criminal underworld while investigating three cases interrelated by the disappearance of his ex-girlfriend and her new wealthy boyfriend.

Here, Wilson appears as Coy Harlingen, a man whose disappearance prompts his wife (Jena Malone) to hire the film’s P.I. protagonist (Joaquin Phoenix) to mount a search. The film was nominated for a number of awards, including two at the 87th Academy Awards and Best Actor – Motion Picture Musical or Comedy for Phoenix at the 72nd Golden Globe Awards.

“When I read the script for Paul Thomas Anderson’s Inherent Vice, I didn’t understand it. I couldn’t understand the movie either! I was excited when Paul asked me to be a part of it, just because I’ve always admired his work. But when I watched the movie, of course, there are some beautiful scenes; scenes between Joaquin and Katherine, the scene with the Neil Young song… So beautiful! But I couldn’t tell you what the movie was about. Sometimes I wouldn’t even be quite sure, like, are these dream sequences?”

4. Wonder (Stephen Chbosky – 2017)

Wonder, based on the 2012 novel of the same name by R. J. Palaciowhich, follows a boy with Treacher Collins syndrome trying to fit in his surroundings. Wilson plays the role of the boy’s father, Nate Pullman, acting alongside Julia Roberts, who plays his mother. The film received mostly positive reviews and was even nominated for an Academy Award.

Wilson is particularly great at playing the loving father, even though it’s a little weird that he now plays the “adult” after years of playing the offbeat, cool guy with some sort of scheme up his sleeve. Wilson says he wasn’t sure about his acting like that of a father. “Yeah, when I first read it, Nate’s character wasn’t clear, and [director] Steve Chbosky said he was going to sort of taking a pass on it and had some ideas. And so he came up with sort of a point of view for the guy that made sense to me and that I could imagine.”

He added: “But yeah, the first couple times, I was like, ‘Is anyone going to really buy me as a parent?’ But yeah, yep, they do.”

3. The Royal Tenenbaums (Wes Anderson – 2001)

Ostensibly based on a nonexistent novel, and told with a narrative influenced by the writing of J.D. Salinger, it follows the lives of three gifted siblings who experience great success in youth, and even greater disappointment and failure in adulthood. The children’s eccentric father Royal Tenenbaum (Hackman) leaves them in their adolescent years, then returns to them after they have grown, falsely claiming he has a terminal illness. He works on reconciling with his children and ex-wife (Huston).

Co-written by Wilson and directed by long-time friend Wes Anderson, The Royal Tenenbaums involves themes of the dysfunctional family, lost greatness, and redemption. An absurdist and ironic sense of humour pervades the film. It was Anderson’s most financially successful film until 2014’s The Grand Budapest Hotel. Hackman won a Golden Globe for his performance, and the screenwriters (including Wilson) were nominated for the Academy Award for Best Original Screenplay. In 2016, it was included in BBC‘s 100 Greatest Films of the 21st Century.

“I love that movie. I think my favourite scene in that movie is when Gene Hackman and Danny Glover come into the kitchen,” Wilson once commented. “Gene Hackman is kind of sitting there and they kind of have some contretemps. And Gene says, ‘Are you tryin’ to steal my woman? …You heard me, Coltrane’. Danny goes, ‘Did you just call me Coltrane?’ Then Gene’s like, ‘No, but if I did, you couldn’t do anything about it’. (Laughs) Just so it doesn’t seem arrogant that I’m quoting this line, Wes wrote that. I’m really appreciating it as a fan.”

2. Bottle Rocket (Wes Anderson – 1996)

In addition to being Wes Anderson’s feature-length directorial debut, Bottle Rocket was also the debut feature for brothers Owen and Luke Wilson, who co-starred with James Caan and Robert Musgrave. It was in this film that we were introduced to the weird eccentricities of Wes Anderson, and also the first of his many collaborations with the Wilson brothers.

Although it was a blip on the commercial radar, Bottle Rocket was subjected to huge praise, being described as “Reservoir Dogs meets Breathless with a West Texas sensibility.” Director Martin Scorsese later named Bottle Rocket one of his top-ten favourite movies of the 1990s.

Wilson’s Dignan was practically a mythical figure, a rogue cowboy in a yellow jumpsuit with no real past or future. His relentless optimism served as an antidote for the disaffected Gen-X ennui of Luke Wilson’s Anthony Adams, the character the film’s target audience was meant to relate to. To much irony, however, when the film failed to achieve financial success, Wilson considered quitting movies and joining the Marines.

1. Midnight in Paris (Woody Allen – 2011)

Owen Wilson gave us his finest performance in Woody Allen’s dreamy masterpiece Midnight in Paris as Gil Pender, a screenwriter, who is forced to confront the shortcomings of his relationship with his materialistic fiancée and their divergent goals, which become increasingly exaggerated as he travels back in time each night at midnight. As he roams, seemingly losing himself around the exotic and nocturnal Paris of the golden age, we too find ourselves to be amongst the glut of shining personas, noticing beauty and finding inner satisfaction through the eyes of Gil.

Exploring themes of nostalgia and modernism, the film opened to critical acclaim and is considered one of Allen’s best films in recent years. In 2012, it won the Oscar for Best Original Screenplay and the Golden Globe Award for Best Screenplay. It was nominated for three other Academy Awards: Best Picture, Best Director and Best Art Direction.

In his production notes about the film, Woody Allen explained why he cast Wilson as Gil: “Owen is a natural actor. He doesn’t sound like he’s acting, he sounds like a human being speaking in a situation, and that’s very appealing to me. He’s got a wonderful funny bone, a wonderful comic instinct that’s quite unlike my own, but wonderful of its kind. He’s a blond Texan kind of Everyman’s hero, the kind of hero of the regiment in the old war pictures, with a great flair for being amusing. It’s a rare combination and I thought he’d be great.”

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