Today we are going to look at one of Hollywood’s most recognizable faces, Owen Wilson. This Texas native has graced our screens for decades with his laid-back charm, offbeat humor, and signature “wow” catchphrase. But despite his countless comedic hits, there have been a few misses along the way. So, without further ado, let’s dive into the list of the least funny Owen Wilson movies.
Owen Wilson’s journey in Hollywood has been a long and storied one. He started with the indie classic in the late 90s Bottle Rocket, which he co-wrote with frequent collaborator Wes Anderson. The film’s success launched his career and set the tone for the kind of roles he would become famous for.
Over the years, Wilson has become known for playing affable, slightly offbeat characters that are both endearing and hilarious. He has been part of some of the biggest comedy hits of the past two decades, including zoolander, Wedding CrashersAnd The Royal Tenenbaums. But despite his reputation as a comedic powerhouse, Wilson has shown surprising range as an actor as well.
He has tackled dramatic roles in movies like The Life Aquatic with Steve Zissou And Midnight in Paris, with a depth and vulnerability that might surprise some of his fans. And his voice acting work in Pixar’s cars franchise has become iconic, making him a beloved figure in the animation world.
But with any actor’s career, there are bound to be some missteps. For Wilson, those missteps came in the form of a handful of movies that weren’t quite right. These movies may have had potential, but for some reason they couldn’t deliver the laughs we’ve come to expect from the actor.
So, whether you’re an Owen Wilson fan or just looking for a movie or two to avoid, join us as we explore the least funny films in his illustrious career.
10 Marmaduke (2010)
Calling all dog lovers! Unfortunately, not even the cutest dog in the world could save this movie from failure. Marmaduke tells the story of a Great Dane who moves to California with his family and struggles to fit into the local dog community. While the premise sounds promising, the execution leaves a lot to be desired.
The characters are one-dimensional, the jokes fall flat, and the storyline is predictable. Not even the addition of some big names, including Emma Stone and Steve Coogan, could save this forgettable film. Owen Wilson plays the titular character, but his signature charm is drowned out by a bland script and uninspired direction. Sorry, Marmaduke, but this movie is a dud.
9 Are You Here (2013)
It’s always a shame when a movie with so much potential doesn’t deliver. Are you here revolves around two best friends, played by Owen Wilson and Zach Galifianakis, who go on a road trip after one of them inherits a large sum of money. The premise is promising, but the execution anything but.
The film contains unlikely characters, a slow pace and the jokes are few and far between. Not even the talent of the two protagonists can save this film from a slumber party. Wilson plays a scruffy weatherman who is meant to be the sympathetic villain, but his performance falls short due to a lack of substance in the script. Overall, Are you here is a forgettable comedy that isn’t quite right.
8 Free Birds (2013)
Thanksgiving may be a time for family, friends, and great food, but this movie fails to capture any of that spirit. Free birds tells the story of two turkeys who go back in time to try to change the course of history and prevent the first Thanksgiving. While the premise is silly and imaginative, the execution falls flat.
The characters are forgettable, the jokes are stale, and the plot is convoluted. Not even the addition of some big voice talent, including Amy Poehler and Woody Harrelson, could save this turkey of a movie. Owen Wilson voices the lead turkey, but his performance is forgettable at best.
7 I Spy (2002)
It’s not uncommon for Hollywood to try and cash in on the popularity of a classic TV show, but I spy missed the target. The film stars Owen Wilson and Eddie Murphy as two spies tasked with recovering a stolen jet. The premise sounds like a recipe for success, but the movie falls flat in pretty much every way.
The jokes are uninspired, the characters are not unusual, and the storyline is much like any other spy comedy. Wilson plays the bumbling sidekick to Murphy’s wisecracking lead, but not even his signature charm can save this film from being a dud.
6 Little Fockers (2010)
Ah, the beloved Fockers franchise. Unfortunately, the third episode, Little Fockers, fails to live up to the hilarity of its predecessors. The movie follows the same dysfunctional family we’ve come to know and love as they prepare for a big birthday party. While the premise sounds promising, the execution leaves a lot to be desired.
The characters are tired, the plot is predictable and the jokes are repetitive. Not even the addition of some big names, including Robert De Niro and Dustin Hoffman, could save this forgettable movie. Wilson plays the same character he played in the previous films, but his charm is overshadowed by the dullness of the script. That being said, Little Fockers is a forgettable entry in the franchise.
5 Father Figures (2017)
In Father figures, Owen Wilson co-stars with Ed Helms as estranged fraternal twins who go on a road trip to find their birth father. Despite the star-studded cast and promising premise, the film falls flat in the comedy genre.
The jokes are unfunny and lack originality, making the film feel more like a tired sitcom than a feature film. Owen Wilson’s performance is mediocre and his comedic timing falls short, making it hard to get any real laughs. While the film’s heart is in the right place, it fails to deliver on its promise of a funny and heartwarming story, ultimately making it one of Owen Wilson’s least funny films.
4 The Big Leap (2004)
The big jump is a crime comedy that sees Owen Wilson as a hobo who gets caught up in a scheme to steal money from a wealthy businessman. Despite its promising set-up and talented cast, the film does not fully appeal to the audience. The humor feels forced and contrived, and Owen Wilson’s character lacks the charm and humor he’s known for.
The film also suffers from a convoluted plot that never quite comes together, leaving the audience feeling confused and unsatisfied. While The Big Bounce had potential, it ultimately fails to deliver on its promise.
3 Zoolander No. 2 (2016)
Zoolander No. 2 is a sequel to the cult classic Zoolander and sees Owen Wilson reprising his role as Hansel McDonald. Unfortunately, the sequel fails to capture the magic of the original and feels rather bland as a comedy film. The jokes are stale and repetitive, and the movie relies too heavily on callbacks to the original movie. Owen Wilson’s performance is lackluster and his character feels like a caricature of his original self. While the film may contain some moments of humor, they are rare.
Zoolander No. 2 suffered from the sequel curse, failed to capture the magic of the original, and relied too heavily on callbacks to the first film. Owen Wilson’s character, Hansel McDonald, lacked the charm and humor that made him a fan favorite in the original film. Overall, the movie fails to recapture the magic of the original, leaving audiences feeling disappointed and awed.
2 Chuck Taylor (2008)
When you combine Owen Wilson’s comedic style with high school awkwardness, you might expect something magical. Unfortunately, Drill Bit Taylor misses the target. The film follows a group of bullied high school students who hire a homeless person, played by Wilson, as a bodyguard. While the premise sounds promising, the execution leaves a lot to be desired.
The characters are generic, the plot is predictable and the jokes are unoriginal. Not even Wilson’s charming performance can save this forgettable comedy from failure. The movie doesn’t give any real depth to the characters or their motivations, making it hard to care about their plight.
1 You, Me and Dupree (2006)
In You, me and DupreeOwen Wilson stars as Dupree, a slacker who moves in with his newlywed friends and destroys their marriage. While the film has some potential for laughs, it ultimately falls flat in the comedy genre. The humor is predictable and lacks originality, with the jokes feeling forced and contrived. Owen Wilson’s performance as Dupree is lackluster, and his character feels like a one-dimensional version of the sympathetic flaccid archetype he’s known for. The other characters also lack depth and can’t really laugh.
The film’s premise had potential, but ultimately fails to deliver on its promise of a funny and heartwarming story. Overall, the film suffers from a lack of originality and forced humor, making it a less funny entry in Owen Wilson’s filmography. While Wilson has proven to be a talented comedian in other films, You, me and Dupree fails to showcase his comedic talents, leaving the audience feeling awed and disappointed.