Paint (2023)
IFC FilmsIn one of his most recent roles, Wilson plays an artist with his own television program, à la Bob Ross. Although his role (and hair and wardrobe) was inspired by the real late painter, the plot—including his rivalry with an up-and-coming artist—is entirely fictional.
2Wedding Crashers (2005)
New Line CinemaMany fans know Wilson from this classic comedy about buddies who sneak into weddings in the hopes of making romantic connections. Much of the film—including the "Lock it up!" scene and the line "I think we only use ten percent of our hearts"—was improvised by the actor.
3The Royal Tenenbaums (2001)
Touchstone PicturesWilson co-wrote and starred in this film about a dysfunctional family reuniting after years of chaos—and it earned him an Academy Award nomination. He turned down a role in Ocean's Eleven for this film—and so did Danny Glover and Owen's brother, Luke Wilson.
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4The Internship (2013)
Twentieth Century FoxWilson and Vaughn reunited for this comedy about salesmen landing internships at Google—and learning that competing with tech-savvy youngsters for a job isn't as easy as they thought. The actors starred alongside 100 extras who were real-life Google employees at the time.
5Fantastic Mr. Fox (2009)
Twentieth Century FoxWes Anderson cast his longtime friend as Coach Skip in this animated tale of foxes versus farmers. Wilson, along with his costars George Clooney and Meryl Streep, recorded their parts outside a traditional studio: They went into a stable in a forest to increase the "spontaneity," Anderson once explained.
6The Grand Budapest Hotel (2014)
Searchlight PicturesIn yet another hit film by Wes Anderson, Wilson plays a concierge-turned-secret-society-member helping to solve a mysterious murder. He bonded with costar Adrien Brody on set, so much so that after claiming he never bowled before, Wilson asked the fellow actor to go bowling one night—and beat him in a game that decided who would pay for their drinks.
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7Wonder (2017)
LionsgatePlaying the father of a boy born with Treacher Collins syndrome, Wilson's performance in this film was especially emotional. "When he came on set as Auggie after going through makeup, he became Auggie. It was easy to love and feel protective toward this brave, little dignified person," he told TODAY of costar Jacob Tremblay.
8Meet the Parents (2000)
Universal PicturesThough Kevin Rawley was a supporting role in this beloved comedy, Wilson made the part entirely his own. In fact, he managed to improvise most of his lines as the wealthy ex-fiancé of Teri Polo's character, Pam.
9Meet the Fockers (2004)
Universal PicturesWilson reprised his role in the much-anticipated sequel, which shows the families of a couple meeting for the very first time. Not surprisingly, he had a great time filming all of the Fockers films. "Ben [Stiller] and I have worked together so much that anytime we're in a scene, we were always kind of laughing and stuff together," he once told CinemaBlend.
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10Little Fockers (2010)
Universal PicturesIn the final movie of the Fockers trilogy, Wilson shared an intimate scene with Barbra Streisand that had audiences cracking up. "To be able to say you kissed Barbra Streisand, that's pretty major. That's one you can check off the to-do list," he joked to CinemaBlend.
11Cars (2006)
Disney/PixarIn an animated classic that defined the childhoods of many, Wilson voices Lightning McQueen, a car making his way to a big race. In a rare move for Pixar, a company that usually promotes its projects without drawing attention to the voices behind its characters, most of the film's marketing was centered around Wilson.
12Cars 2 (2011)
Disney/PixarWilson reprised his iconic role after the first was a hit, this time taking Lightning McQueen to the World Grand Prix. The film earned a nomination for the Academy Award for Best Animated Film—the very first Pixar movie to ever be nominated in the category.
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13Cars 3 (2017)
Disney/PixarFeeling pushed out of the sport by a new generation of race cars, Lightning McQueen sets out to prove he still has what it takes to be a champion. Wilson was able to tap into his animated character's emotions, thanks to NASCAR legend Jeff Gordon, who served as a consultant on the film.
14Zoolander (2001)
Paramount PicturesStiller and Wilson costarred together again in this hit comedy about male models turned secret agents. Fun fact: Wilson's memorable long blonde hair in the movie was a wig because he was filming Behind Enemy Lines at the time and had to keep his real hair short.
Zoolander 2 (2016)
Paramount PicturesA whopping 15 years later, audiences were thrilled when the stars reunited for the sequel. To announce the film, Wilson and Stiller dressed up as their characters and hit the Paris runway. Wilson didn't expect such a positive reaction, telling Collider, "When we first announced the movie at the Paris fashion show, we didn’t know what the reaction would be, but it seemed to be like a rock concert."
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16Marley & Me (2008)
Twentieth Century FoxIn this rom-com, Wilson and Jennifer Aniston play newlyweds whose lives change forever after adopting a troublemaking puppy. In addition to working with 22 different dogs throughout the film, he also got to perform alongside his real-life parents, who played his character's parents.
17Behind Enemy Lines (2001)
Twentieth Century FoxWilson's career took a dramatic turn with this intense film about a pilot being shot down over war-torn Bosnia. To prepare for the role, the actor rode in a jet at supersonic speeds. Though he separated his shoulder during a stunt, he was back filming more physical scenes the next day.
18No Escape (2015)
The Weinstein CompanyIn another role that strayed from Wilson's usual lighthearted comedies, he portrays a father who finds himself and his family caught in the middle of an international coup. He later told Collider: "I guess the thing that attracted me to the script was that it didn't feel too action-y. It felt grounded in believability."
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19She's Funny That Way (2014)
LionsgateIn this comedy, the actor took on the role of a playwright whose life goes awry when his project leads to an unexpected love triangle. Director Peter Bogdanovich originally put the film on hold after his first choice for the lead, John Ritter, passed away. After Wes Anderson introduced Bogdanovich to Wilson years later, he decided to bring it back.
20Starsky & Hutch (2004)
Warner Bros.This buddy cop comedy follows Stiller and Wilson's characters as they catch criminals in their red and white Ford Gran Torino. When Wilson's character sings "Don't Give Up on Us Baby," the voice was actually that of David Soul, who played the original Ken Hutchinson in the 1975 television series.
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