The exceptional Bruce Willis has crafted an outstanding Hollywood resume over the course of his 40-year career, fearlessly tackling every genre. After achieving widespread fame with his role in the ‘80s comedy-drama series Moonlighting, the seasoned performer went on to become a worldwide action hero with his role as the sarcastic John McClane in the epic 1988 flick Die Hard. He would go on to star in a slew of dynamic and critically-acclaimed pictures, showing off his natural gift for humor in popular flicks like Look Who’s Talking, Red and Cop Out.

Willis has proven time and time again that he’s far more than just a brooding leading man, demonstrating his comedic chops and undeniable star power constantly throughout his enviable career. His sardonic delivery of lines and willingness to embrace the quirky and strange have helped make Willis one of the most successful box office draws of all time. Having worked with revered directors like Wes Anderson, Robert Zemeckis, and Robert Rodriguez in the comedy genre, Willis is undoubtedly a jack of all trades in the entertainment business. His ability to inject even a serious action movie with witty, sarcastic humor makes it sometimes difficult to separate his action films from his comedy films, but these are the movies which show Bruce Willis at his funniest best.

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9 The Whole Nine Yards

     Warner Bros.

Bruce Willis and Matthew Perry teamed up to star in the 2000 crime comedy The Whole Nine Yards, telling the story of the charismatic but unhappy dentist Nicholas “Oz” Oseransky, who makes the startling discovery that his new next-door neighbor Jimmy is actually a notorious Chicago contract killer with a large bounty on his head. At the insistence of his money-hungry wife, Oz decides to inform the mob boss of his whereabouts in exchange for the reward. Willis showed off his comedic chops in the entertaining picture, brilliantly portraying gangster Jimmy “the Tulip” Tudeski and showcasing his undeniable on-screen chemistry with Perry. The actor would later famously guest star on Friends after appearing in the comedy, having lost a bet to Perry after The Whole Nine Yards topped the box office. The two teamed up again for a sequel, The Whole Ten Yards.

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

8 The Last Boy Scout

The 1991 buddy action comedy The Last Boy Scout features an impressive cast including Bruce Willis, Damon Wayans, and Halle Berry, and is considered one of the best films directed by Tony Scott. The movie follows private investigator Joe Hallenbeck as he warily finds himself joining forces with the boyfriend of a female witness he was hired to protect to investigate the violent crime. Despite an initially mixed reaction by critics, the flick was still a box office success and helped Willis recover his cinema star status after the failure of his other comedy project Hudson Hawk that same year. Since its initial release, The Last Boy Scout has garnered a passionate following as a ’90s cult classic and has since been praised for the sharp screenplay, delightful chemistry between Willis and Wayans and the overall direction of the movie.

7 Look Who’s Talking

     Tri-Star Pictures

Bruce Willis once again showed off his talents as a dynamic performer when he hilariously portrayed the narrating baby Mikey in the 1989 romantic comedy Look Who’s Talking, offering amusing commentary on the state of his mother Mollie’s love life and her blossoming relationship with suitor James in the clever film. Director Amy Heckerling (of Fast Times at Ridgemont High and Clueless fame) got the idea for the playful picture from her own young daughter, who would always look around in her baby seat; she once revealed, “My husband and I started to put words in her mouth, what she might be thinking based on her expressions.” Co-starring John Travolta and Kirstie Alley, the rom-com was a surprise hit at the box office and went on to earn $297 million, spawning two popular sequels and the short-lived ABC sitcom Baby Talk.

6 Death Becomes Her

     Universal Pictures

Robert Zemeckis directed the cult classic 1992 satirical black comedy Death Becomes Her, telling the spellbinding story of a narcissistic, fading actress who discovers a magic potion that grants them eternal youth and immortality, but with some undesirable repercussions. Meryl Streep, Goldie Hawn, and Bruce Willis star in the dark fantasy comedy, with the renowned actresses portraying life-long frenemies vying for the affection of the same man (Willis), both of whom take the potion in hopes of winning him over.

The film is widely regarded as a pioneer in its impressive use of computer-generated effects, having been the first to use photo-realistic human skin software. Death Becomes Her has gone on to acquire a prominent following, especially in the LGBTQ+ community, with Vanity Fair calling the comedy “a touchstone of the queer community.”

5 Cop Out

     Warner Bros. Pictures

Bruce Willis teamed up with the always hilarious Tracy Morgan for the 2010 buddy cop action-comedy Cop Out, in which the entertaining duo portray seasoned NYPD partners Jimmy Monroe and Paul Hodges, who investigate the theft of Jimmy’s highly-coveted, mint-condition baseball card that was stolen by a memorabilia-connoisseur gangster. While there was no shortage of drama during the production and aftermath of the comedy (Willis and director Kevin Smith notoriously butted heads), Cop Out still went on to become Smith’s most financially successful project to date and showcased the comical on-screen chemistry between Willis and Morgan. In the wake of the actor’s retirement from filmmaking due to his ongoing battle with aphasia, Smith publicly apologized for his disparaging past comments towards Willis.

4 Planet Terror

     Dimension Films

The innovative Robert Rodriguez helmed the 2007 action horror comedy Planet Terror, which follows a shabby group of biochemical outbreak survivors who are forced to fend off a terrifying horde of zombie-like creatures in rural Texas. Longtime Rodriguez friend and collaborator Quentin Tarantino helped bring the freaky flick to life, with co-star Marley Shelton stating, “Quentin was on set a lot. He had notes and adjustments to our performances and he changed lines every once in a while. Of course, he always deferred to Robert on Planet Terror and vice versa for Death Proof. So it’s really both of their brainchild.”

Bruce Willis appeared alongside actors Rose McGowan and Josh Brolin for the horror comedy, amusingly portraying the deranged Lieutenant Muldoon who contributed to the gruesome zombie outbreak.

3 Red

     Summit Entertainment 

Touting a star-studded cast of Hollywood elite like Bruce Willis, Morgan Freeman, and Helen Mirren, the 2010 action comedy Red centers on the bored and retired black-ops agent Frank Moses (Willis) as he reassembles his lethal old team in order to defeat a high-tech assassin and dangerous group of hit men. Tagged as R.E.D. (Retired, Extremely Dangerous), the squad must once again put their special skills to good use in order to break into CIA headquarters and expose an enormous conspiracy.

Loosely based on the Homage Comics series of the same name, Red went on to become a critical and commercial hit, grossing $199 million at the box office and leading to a 2013 sequel; in their glowing review, the Sydney Morning Herald called the comedy “While it’s a movie richly endowed with big names, you come away imbued with the happy thought that they all left their egos at home."

2 Moonrise Kingdom

     Focus Features

Renowned filmmaker Wes Anderson directed the 2012 coming-of-age comedy-drama Moonrise Kingdom, telling the heartwarming tale of two 12-year-olds who fall in love in 1965 and decide to run away from their coastal New England town. The island’s police captain Sharp (Bruce Willis) bans together with a group of peculiar residents to track down the lovestruck kids and bring them home.

When discussing the Oscar-nominated picture and working with Anderson, Willis opened up to the Huffington Post, calling it one of the projects he’s most proud of: “Moonrise Kingdom is a very novel story. There’s nothing like it, except another Wes Anderson film. And even in his library, I think he would say, too, that Moonrise Kingdom was really different than anything he has ever done.” The dramedy premiered at the Cannes Film Festival and garnered universal acclaim, with the BBC calling it one of the greatest films of the 21st century.

1 Die Hard

     20th Century Fox

Bruce Willis became a certified movie star when he memorably portrayed the iconic, wise-cracking New York City police detective John McClane in the 1988 action classic Die Hard, which follows the reluctant hero as he faces off against German terrorists who have taken a Los Angeles skyscraper hostage. Famous for his biting one-liners, including his beloved famous catchphrase “Yippee-ki-yay, motherfu**er," McClane provided hilarious and colorful commentary as he begrudgingly fights to take down villain Hans Gruber, brilliantly entertaining audiences every step of the way. Willis’ performance in the ‘80s staple helped redefine the face of the action genre, with the actor’s portrayal of McClane inspiring a new wave of everyday hero characters who manage to save the day with an average physique and sardonic humor to boot.