Today, we're going to take a 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 Owen Wilson's least funny movies.

Owen Wilson's journey in Hollywood has been a long and storied one. He got his start in the late 90s with the indie classic Bottle Rocket, which he co-wrote with frequent collaborator Wes Anderson. The film's success launched his career and set the tone for the type of roles he would become famous for.

Over the years, Wilson has become known for playing affable, slightly off-kilter characters who are both endearing and hilarious. He's been a part of some of the biggest comedy hits of the last two decades, including Zoolander, Wedding Crashers, and The Royal Tenenbaums. But despite his reputation as a comedic powerhouse, Wilson has also shown a surprising range as an actor.

Related: Owen Wilson’s Best Comedy Movies, Ranked

He's tackled dramatic roles in films like The Life Aquatic with Steve Zissou and Midnight in Paris, showcasing a depth and vulnerability that might surprise some of his fans. And his voice acting work in Pixar's Cars franchise has become iconic, cementing him as a beloved figure in the animation world.

But with any actor's career, there are bound to be some missteps. For Wilson, those missteps have come in the form of a handful of movies that didn't quite hit the mark. These films might have had potential, but for one reason or another, they failed to deliver the laughs we've come to expect from the actor.

So, whether you're an Owen Wilson fan or just looking for a few movies to avoid, join us as we explore the least funny films in his illustrious career.

10 Marmaduke (2010)

The titular dog Marmaduke
Netflix

Calling all dog lovers! Unfortunately, even the cutest pooch in the world couldn't save this movie from falling flat. Marmaduke tells the story of a Great Dane who moves to California with his family and struggles to fit in with the local canine community. While the premise sounds promising, the execution leaves much to be desired.

The characters are one-dimensional, the jokes fall flat, and the storyline is predictable. Even the addition of some big-name talent, including Emma Stone and Steve Coogan, couldn't salvage this forgettable flick. Owen Wilson plays the titular character, but his trademark charm is drowned out by a lackluster script and uninspired direction. Sorry, Marmaduke, but this movie is a dud.

9 Are You Here (2013)

Are You Here
Lionsgate

It's always a bummer when a movie with so much potential fails to deliver. Are You Here centers 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 is anything but.

The movie features unlikable characters, and sluggish pacing and the jokes are few and far between. Even the talent of the two leads can't save this movie from being a snooze-fest. Wilson plays a sleazy weatherman who is meant to be the lovable rogue, but his performance falls flat due to a lack of substance in the script. All in all, Are You Here is a forgettable comedy that doesn't quite hit the mark.

8 Free Birds (2013)

Free Birds
Relativity Media

Thanksgiving may be a time for family, friends, and delicious 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 and change the course of history and prevent the first Thanksgiving. While the premise is wacky and imaginative, the execution falls flat.

The characters are forgettable, the jokes are stale, and the plot is convoluted. Even the addition of some big-name voice talent, including Amy Poehler and Woody Harrelson, couldn't save this turkey of a movie. Owen Wilson voices the lead turkey, but his performance is forgettable at best.

7 I Spy (2002)

ispy
Columbia Pictures

It's not uncommon for Hollywood to try and cash in on the popularity of a classic TV show, but I Spy missed the mark. The movie 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 just about every way.

The jokes are uninspired, the characters are not unusual, and the storyline is pretty much like every other spy comedy. Wilson plays the bumbling sidekick to Murphy's wisecracking lead, but even his signature charm can't save this movie from being a dud.

Related: These Are Some of the Funniest Cop Comedies, Ranked

6 Little Fockers (2010)

owen wilson little fockers
Dreamworks Pictures

Ah, the beloved Fockers franchise. Unfortunately, the third installment, 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 much to be desired.

The characters are tired, the plot is predictable, and the jokes are repetitive. Even the addition of some big-name talent, including Robert De Niro and Dustin Hoffman, couldn't save this forgettable flick. Wilson plays the same character he's played in the previous movies, but his charm is overshadowed by the blandness of the script. That said, Little Fockers is a forgettable entry in the franchise.

5 Father Figures (2017)

Father Figures Trailer Has Owen Wilson & Ed Helms on a Dad Hunt

In Father Figures, Owen Wilson stars alongside Ed Helms as estranged fraternal twins who embark on a road trip to find their biological father. Despite its star-studded cast and promising premise, the movie falls flat in the comedy genre.

The jokes aren’t funny and lack originality, making the movie feel more like a tired sitcom than a feature film. Owen Wilson's performance is lackluster, and his comedic timing falls short, failing to generate any significant laughs. While the movie'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 movies.

4 The Big Bounce (2004)

owen wilson in the big bounce
Warner Bros.

The Big Bounce is a crime comedy that sees Owen Wilson as a drifter who gets caught up in a scheme to steal money from a wealthy businessman. Despite its promising setup and talented cast, the movie doesn’t quite charm the audiences. The humor feels forced and contrived, and Owen Wilson's character lacks the charm and wit that he's known for.

The movie also suffers from a convoluted plot that never quite comes together, leaving the audience feeling confused and unsatisfied. While The Big Bounce may have had potential, it ultimately fails to deliver on its promise.

3 Zoolander No. 2 (2016)

Zoolander 2
Paramount Pictures 

Zoolander No. 2 is a sequel to the cult classic comedy Zoolander and sees Owen Wilson reprising his role as Hansel McDonald. Unfortunately, the sequel fails to capture the magic of the original, feeling rather bland as a comedy movie. The jokes are stale and repetitive, and the movie relies too heavily on callbacks to the original film. Owen Wilson's performance is lackluster, and his character feels like a caricature of his original self. While the movie may have some moments of humor, they are few and far between.

Zoolander No. 2 suffered from the sequel curse, failing to capture the magic of the original and relying too heavily on callbacks to the first film. Owen Wilson's character, Hansel McDonald was lacking the charm and wit that made him a fan favorite in the original movie. Overall, the movie fails to recapture the magic of the original, leaving audiences feeling disappointed and underwhelmed.

Related: 14 Comedy Sequels That Are Funnier Than the First Movie

2 Drillbit Taylor (2008)

drillbit taylor
Paramount Pictures

When you combine the comedic stylings of Owen Wilson with the awkwardness of high school, you might expect to get something magical. Unfortunately, Drillbit Taylor misses the mark. The movie follows a group of bullied high schoolers who hire a homeless man, played by Wilson, as their bodyguard. While the premise sounds promising, the execution leaves much to be desired.

The characters are generic, the plot is predictable, and the jokes aren’t original. Even Wilson's charming performance can't save this forgettable comedy from being a misfire. The movie fails to provide any real depth to the characters or their motivations, making it difficult to care about their plight.

1 You, Me And Dupree (2006)

owen wilson in you, me and dupree
Avis-Davis Productions

In You, Me And Dupree, Owen Wilson stars as Dupree, a slacker who moves in with his newlywed friends and wreaks havoc on their marriage. While the movie 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 lovable slacker archetype he's known for. The other characters also lack depth and fail to generate any real laughs.

The movie's premise had potential but ultimately fails to deliver on its promise of a funny and heartwarming story. Overall, the movie suffers from a lack of originality and forced humor, making it a less funny entry in Owen Wilson's filmography. While Wilson has proven himself to be a talented comedian in other films, You, Me And Dupree fails to showcase his comedic talents, leaving audiences feeling underwhelmed and disappointed.