Luke and Owen Wilson are both among the most famous actors of their generation. From critical darlings to box office successes, they’ve appeared in some of the most popular movies of the 21st Century. However, some film fans may not realize that they have an older brother, named Andrew, who’s appeared in numerous films with either Luke or Owen, and in some cases, even both. All three brothers got their start alongside American filmmaker Wes Anderson, whom Owen met in college.
The Wilsons starred in Anderson’s debut feature, Bottle Rocket (1996). Ever since, they’ve worked with the director on numerous occasions, while also collaborating with a group called the Frat Pack, which consists of famous names like Ben Stiller, Will Ferrell, Vince Vaughn, and Jack Black. Alongside other Hollywood superstars, all three Wilson brothers have played a part in some hilarious modern comedies, and this list will shine light on the best. These are the best films that feature multiple Wilson brothers, ranked.
6 Zoolander (2001)
Starring Owen and Andrew Wilson
Among the most famous comedies of the 21st Century is Zoolander (2001), directed by Ben Stiller. He also co-wrote the script with John Hamburg and Drake Sather, while famously providing the eponymous effort: Derek Zoolander, a male model. Owen Wilson plays Hansel, his nemesis-turned-ally, while Christina Taylor plays Matilda, his love interest.
Hilarious Performances
All three lead actors share engaging chemistry while exchanging uproarious lines of unforgettable dialogue. And while Zoolander wasn’t exactly a hit with critics, audiences hold it in high regard. And justifiably so. Ben Stiller and Owen Wilson are among the greatest acting collaborators of the century, and this is perhaps their most hilarious movie. They sell their parts as dimwitted models to perfection, and frankly, everyone involved puts forth hilarious efforts — that includes Andrew Wilson, even if his role as Hansel’s corner guy was rather minor overall.
The success of Zoolander led to a sequel in the following decade, though only Owen appears as far as the Wilson brothers are concerned. Not that it matters for the sake of the list — the sequel pales in comparison to its original counterpart. The latter holds up today as one of the funniest movies by everyone involved, and that will forever be the case. Stream on Paramount+
5 The Wendell Baker Story (2005)
Directed by Luke and Andrew Wilson, and starring Luke and Owen Wilson
Directed by Luke and Andrew Wilson from the former’s original script, The Wendell Baker Story (2005) also features Luke in the titular role. It’s perhaps the most underrated movie of his career. Critically and commercially, The Wendell Baker Story came up short. In reality, it’s worth far more loved today as a high-quality comedy with a star-studded cast.
Peak Luke Wilson
This is one of Luke Wilson’s most charismatic performances — he rattles off his own witty dialogue at a rapid yet soothing pace. His brother Owen makes a supporting appearance as the head nurse at a retirement home in which Wendell begins to work, while Eva Mendes plays Wendell’s love interest, named Doreen. Everyone performs to perfection, most notably the two Wilsons. There are legitimate nuances to their comedic approach, with hilarious expressions and careful intonations.
Each actor is at their comedic peak in The Wendell Baker Story, which also features an engaging story and brilliant pacing, even if its success implies otherwise. With a mediocre response from industry pundits (a 40% approval rating on Rotten Tomatoes) and even worse numbers re: the box office, this should be known as the most underrated film by both Luke and Owen Wilson. Stream on Prime Video
4 Bottle Rocket (1996)
Co-written by Owen Wilson, and starring Owen, Luke, and Andrew Wilson
Marking Wes Anderson’s directorial debut, Bottle Rocket was co-written by Anderson and Owen Wilson. The two met in college, even roomed together, and they first made Bottle Rocket as a short. Both films, the short and the feature, were filmed throughout their home state of Texas, and they recruited another local actor to co-star alongside Owen. Of course, that would be his younger brother, Luke.
An Acclaimed Debut with a Star-Studded Cast
After being released from a mental institution, Anthony (played by Luke) is convinced by his friend, Owen’s character Dignan, to commit a massive crime spree. It’s a compelling plot, with other characters being played by the likes of James Caan — as Dignan’s boss, Abe Henry — along with the eldest Wilson brother. Andrew shows up as Jon Mapplethorp, and sure, his role is once again smaller than those of his brothers. But with Bottle Rocket, all three of them marked their on-screen debuts.
Despite its dearth of name value, this is a high-quality film that gave rise to several popular Hollywood names. Upon release, Bottle Rocket received great reviews from critics, with filmmakers like Martin Scorsese even citing this Anderson debut as one of the top 10 movies of the 1990s. And even today, nearly three decades down the line, Bottle Rocket remains among the most essential movies that all three Wilson brothers have to offer. Stream on Prime Video
3 Idiocracy (2006)
Starring Luke and Andrew Wilson
After agreeing to take part in a hibernation experiment run by the government, the protagonist of Idiocracy (2006) wakes up in the year 2505. Played by Luke Wilson, his name is Joe Bowers, and alongside Maya Rudolph’s character Rita, they traverse a dystopian society controlled by corporations who capitalized on the many technological developments of the twenty-first century.
A Creative Force of Comedy
Idiocracy
- Release Date
- September 1, 2006
- Runtime
- 84
Humans are now incapable of living on their own, like Neanderthals re: their intelligence quotients. This plot paves the way for some truly hilarious moments thanks primarily to director Mike Judge, who co-wrote the script with Etan Cohen. And while those names may appear unfamiliar to select film fans, almost everyone will recognize the supporting members of Idiocracy‘s star-studded cast.
Alongside Wilson and Rudolph, there’s also Dax Shepard, Terry Crews, and Justin Long. Three comedic legends, all at the peak of their careers. The other Wilson brother among the cast of Idiocracy is Andrew, who appears as a rehabilitation officer known as Beef Supreme. It’s perhaps the most prominent role of his underrated career. And although the entire movie is just as silly as his character’s name, Idiocracy remains entirely entertaining until the farcical frames of its finale. Rent on YouTube
2 Rushmore (1998)
Co-written by Owen Wilson, and starring Luke and Andrew Wilson
Directed by Wes Anderson and, once again, co-written by the youngest Wilson brother, Rushmore (1998) features the other two — Luke and Andrew — among the cast, albeit in minor fashion. For his first several films, Anderson cast at least one of the Wilson siblings in his projects. But with Rushmore, there are two separate names worth noting: Jason Schwartzman, and Bill Murray. The plot homes in on Schwartzman’s protagonist, named Max.
A Cast of Quirky Characters
Rushmore
- Release Date
- December 11, 1998
- Runtime
- 93
He loves his school, the eponymous Rushmore Academy, even if he by no means excels in class. He’s more of an extracurricular kind of guy, and he loves meeting figures associated with his beloved prep school. Soon into the plot, Max befriends a wealthy business magnate named Herman Blume, played by Murray, and they both fall in love with a new teacher: Rosemary Cross, who’s played by Olivia Williams. They shine as some of Anderson’s quirkiest characters, and each actor shares engaging chemistry with the next.
Known for his star-studded casts, Anderson recruited two of his old pals — Luke and Andrew Wilson, that is — while also finding two new thespians to add to his stable of collaborators. Since Rushmore‘s release, Schwartzman and Murray have worked with Anderson six and eight times, respectively. They’re among his most famous collaborators, and Rushmore remains one of their best movies to-date. The same can be said for all three Wilsons. While Luke and Andrew’s on-screen appearances are few and far between, Owen’s screenwriting efforts should be heralded forever. Rent on YouTube
1 The Royal Tenenbaums (2001)
Co-written by Owen Wilson, and starring Owen, Luke, and Andrew Wilson
At the turn of the century, The Royal Tenenbaums (2001) marked the third-straight Wes Anderson movie to which all three Wilson brothers were attached. Owen helped his longtime collaborator pen the script, and he played a supporting (often scene-stealing) character named Eli Cash. Meanwhile, Luke Wilson appears as Richie, one of the members of the Tenenbaum family, while Andrew Wilson has a minor role in a flashback scene.
Wes Anderson’s Masterpiece
Luke and Owen share hilarious chemistry in The Royal Tenenbaums, delivering some of the movie’s most memorable dialogue with keen comedic timing. This is among the most important films of their respective careers, with Owen being nominated alongside Anderson for Best Original Screenplay at the 74th Academy Awards. And justifiably so, as they developed dozens of indelible personalities to convey an emotional tale.
Gene Hackman and Angelica Huston play the parents of the Tenenbaum family, while Gwyneth Paltrow and Ben Stiller play Richie’s siblings — Margot and Chas, respectively. In supporting roles are Bill Murray and Danny Glover, resulting in one of the greatest movie casts ever assembled. Everyone performs perfectly under Anderson’s direction, and (with Owen’s help) this is perhaps his wittiest script yet by dint of well-written dialogue and thought-out character dynamics. Anyone who argues The Royal Tenenbaums as his masterpiece would not be in the minority. Rent on YouTube
