There aren't many actors that audiences associate with pure quality, and while Bruce Willis got a little more cavalier with his movie choices in the late 2000s and 2010s, his name was attached to the very best movies of the 1990s.

Many of Willis' movies changed the course of Hollywood in a major way and are hugely iconic. And with the announcement of Willis' retirement, it's worth looking back at the movies he helped become such a huge part of pop culture and that current Letterboxd users still can't get enough of.

UPDATE: 2022/09/25 12:11 EST BY SHAWN S. LEALOS

With Bruce Willis retiring earlier in 2022, Hollywood lost one of its most iconic action stars. He was the man who changed how Hollywood looked at action heroes, playing an every-man rather than a muscled bodybuilder with lots of guns. He parlayed that into a career that added in some sci-fi action movies and comedy roles along the way and became one of the most beloved movie stars in the world. While his later output was mostly B-grade action projects, he left a trail of movies behind him after his retirement that Letterboxd fans rank among the best in the genre.

The Last Boy Scout (1991) - 3.4

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Joe and Jimmy standing together in The Last Boy Scout.

The Last Boy Scout came out when Bruce Willis was at the top of his game, following the immense success of the Die Hard franchise. With a script by Lethal Weapon writer Shane Black and directed by Tony Scott, Willis starred as Joe, a disgraced Secret Service agent now working as a private investigator.

Joe is hired to bodyguard for someone named Cory, and after her death, he ends up teaming with her boyfriend, a disgraced former football player banned for gambling, played by Damon Wayans. This was an odd-couple pairing, and both Willis and Wayans turned in fun roles that resulted in an underrated and mostly forgotten 90s action movie.

Looper (2012) - 3.5

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Bruce Willis with a gun holding Joseph Gordon-Levitt in Looper

Rian Johnson directed Looper as his third feature, taking on the idea of a time travel film. In this movie, time travel is possible, but only in certain situations, and the crime world uses this to eliminate dead bodies without detection. However, they also have a way to retire assassins, by sending back older versions for the younger ones to kill.

Things go wrong when Joe (Bruce Willis) is sent back to die, but fights his younger self (Joseph Gordon-Levitt) and sets out to get revenge against the people who betrayed him. The movie was interesting, with Levitt doing his best to imitate a younger Bruce Willis, but it was the older actor who really carried the story.

Lucky Number Slevin (2006) - 3.5

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Mr. Goodkat pointing a gun in Lucky Number Slevin.

Directed by Paul McGuigan, Lucky Number Slevin was a crime thriller with Josh Hartnett playing a hapless guy who is kidnapped by rival mob bosses in a case of mistaken identity. He is ordered to kill someone, or they will kill him. Bruce Willis stars as Mr. Goodkat, the man pulling all the strings.

The movie gave Willis a chance to appear in a similar movie to the more successful Pulp Fiction. However, while Willis was the lackey fighting back in the Tarantino movie, here he got the chance to play the master manipulator.

Grindhouse (2007) - 3.6

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Lt. Muldoon in Planet Terror.

In 2007, Quentin Tarantino and Robert Rodriguez teamed up to create the double-feature called Grindhouse. For Rodriguez's part of the movie, he directed Planet Terror, a horror movie where a biochemical outbreak creates what is basically a zombie infestation.

While Rose McGowan is the main hero fighting the outbreak, Bruce WIllis also plays an important role as the villainous Lt. Muldoon, the man who accidentally releases the toxins into the air and starts the entire mess to begin with. This movie gave Willis a chance to play one of the evilest roles of his career.

Nobody's Fool (1994) - 3.6

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Paul Newman and Bruce Willis sitting at the bar in Nobody's Fool

Nobody's Fool was mostly a Paul Newman vehicle, but Bruce Willis was there as a nemesis throughout the movie. The story follows Sully, a freelance construction worker who schemes to keep ahead by doing things like constantly suing a local contractor named Carl for a variety of offenses, although always failing.

Willis plays Carl, and while he is not a genuine bad guy, the fact he is always at odds with Sully makes him someone viewers have no problems rooting against. It is a rare unlikable role for Willis, but one that he pulls off well.

Death Becomes Her (1992) - 3.6

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Ernest painting Madeline's skin in Death Becomes Her

While Die Hard arrived in 1988 and proved that the actor could carry a movie and could be an action hero, Death Becomes Her proved Willis can act. The movie was originally critically panned when it was first released in 1992, and it underperformed at the box office too, despite its star power of Willis, Meryl Streep, and Goldie Hawn.

However, it has since become a cult classic and is loved by cinephiles for its gothic but camp aesthetic. What's most admirable about the movie is that, even though Willis was a ladies' man and action star at the time, he wasn't afraid to act silly and look goofy for the wacky comedy.

Sin City (2005) - 3.6

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Bruce Willis and Jessica Alba in Sin City

Sin City is very much a multi-stranded neo-noir narrative with an ensemble cast, and every character is so strange with their own unique quirks. However, given that Bruce Willis' gruff demeanor is something only he can do, the grumpy every-man character of Detective John Hartigan is the perfect role for the actor, and he steals the show whenever he's on the screen.

Hartigan calls to memory another character called John that Willis played, the iconic John McClane, and they both share a lot of characteristics. But it's so fascinating to see Willis in a movie that's so unapologetically stylish and full of oddball characters. The actor hadn't let his hair down in a movie that's as much about the aesthetic as it is about the narrative since The Fifth Element, which came 8 years earlier.

Die Hard With A Vengeance (1995) - 3.6

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Bruce Willis and Samuel L Jackson in Die Hard with a Vengeance

The second Die Hard movie was a fine popcorn flick, but it essentially repeated the same story of the original movie beat for beat, only it was set in an airport instead of a skyscraper. However, Die Hard with a Vengeance, the third movie in the series, took the franchise to New York, which was the first of many refreshing changes.

The film had the style of a buddy-cop comedy more than anything, as it teamed up Willis and Samuel L. Jackson, who sped around New York solving a villain's clues almost like Batman and Robin solving the Riddler's puzzles. The 1995 movie is by far the best of the four Die Hard sequels, and some even think it's better than the original.

The Fifth Element (1997) - 3.7

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Leeloo and Korben Dallas with the Fifth Element multipass.

Just like Sin City, The Fifth Element sees Bruce Willis playing an everyman surrounded by strange and peculiar characters. The 1997 film is a weird science fiction blockbuster with an even weirder cast that, on paper, wouldn't gel.

Along with Willis, the movie stars Gary Oldman, who plays Jean-Baptiste Emanuel Zorg, an evil and hammy space dictator, and comedian Chris Tucker, who plays flamboyant talk-show host Ruby Rhod. But somehow, the movie works, it's so much fun, and it has the aesthetic of a Ru Paul-directed Star Wars movie.

Unbreakable (2000) - 3.7

* Available to rent on Apple TV & Prime Video

Bruce Willis in Unbreakable, standing in a comic book store

Unbreakable was the start of an unlikely and unexpected movie universe, as the series continued with the surprise sequel Split, and then the team-up movie Glass. And while those films are entertaining in their own right, they can't compete with the philosophical questions that Unbreakable asks and the unique approach it has to comic book tropes.

Though Willis never played a major superhero, despite fans wanting him to appear in the MCU, David Dunn (Willis) is very much a more realistic version of a superhero. And he low-key has one of the most interesting hero/villain dynamics with Mr. Glass.

12 Monkeys (1995) - 3.8

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James in a bio-hazard suit in 12 Monkeys

In an interview with Aint It Cool News, Willis revealed his favorite movies of all time, and of all 14 of them, there was only one sci-fi movie on the list. That film was Alien, one of the most thought-provoking and profound films ever made, so his love of the 1979 movie could be what made him take the starring role in 12 Monkeys, a similarly profound and mind-blowing sci-fi movie.

The film follows a man who travels from the future to learn what caused a deadly virus that kills the entire population. The movie's complex narrative requires multiple re-watches, not only to grasp what's going on, but because it's a visual spectacle.

The Sixth Sense (1999) - 4.0

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Cole (Haley Joel Osment) speaking to Malcolm (Bruce Willis) in The Sixth Sense

The Sixth Sense was a phenomenon when it was released. Through sheer word of mouth, the movie managed to earn $670 million worldwide, which is all the more impressive considering it had a budget of just $40 million. While the box office intake was certainly helped by Willis's starring role, audiences hadn't seen anything like it until 1999.

The movie established writer-director M. Night Shyamalan's style of delivering huge, jaw-dropping twists. And while that might have been a case of diminishing returns throughout his career, there was nothing more shocking than that reveal in the film's closing moments.

Moonrise Kingdom (2012) - 4.0

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Captain Sharp holds up a photograph of a boy in Moonrise Kingdom

2012 was a huge year for Willis, as he starred in the exciting sci-fi action blockbuster Looper, which again saw him traveling back in time, just like 12 Monkeys. But 2012 also saw him star in a more modest, wholesome, and character-driven movie, Moonrise Kingdom.

Though Willis doesn't play the main character in Moonrise Kingdom, as the film is about two 12-year-olds who fall in love, he does have the most important adult role in the movie. And his performance is shockingly moving, especially at this point in his career. The 2012 movie features the last great Willis performance, and it's made even better by being in the middle of an animated-looking, inventive, Wes Anderson-directed world.

Die Hard (1988) - 4.1

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Bruce Willis jumping in Die Hard

People will debate for years over whether or not Die Hard is a Christmas movie. But regardless of whichever camp audiences belong to, there's no denying that the 1988 blockbuster is one of the best action films of all time.

The film was ridiculously influential, as there have been so many knock-off action movies that are all set in one location with a John McClane-type character. But none of them will ever come close to the lightning-in-a-bottle magic of the original. Even despite Willis's career going on for another 34 years after the movie, Die Hard is still considered one of the best flicks Bruce Willis ever filmed.

Pulp Fiction (1994) - 4.3

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Pulp Fiction's Bruce Willis On A Motorcycle

As Samuel L. Jackson, Uma Thurman, and John Travolta appeared on stage at this year's Academy Awards to celebrate the 28th anniversary of Pulp Fiction, it wasn't the same without Willis up there. While Pulp Fiction has a great ensemble cast full of unique characters, Butch had the best scenes.

Whether it's the initial meeting with Marsellus Wallace, the vignette-like sequence in the taxi with Esmerelda, or when he murders Vincent, Butch could be seen as the protagonist of Pulp Fiction. The 1994 classic is one of the most important Hollywood movies ever, and Willis is a major part of its legacy.

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