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10 Movies That Made 1999 an Iconic Year In Film

Since being lionized in Brian Rafferty’s book Best. Movie. Year. Ever., it’s easy to see why Rafferty made the case that 1999 was one of the great years cinema had to offer. There are undeniable canonical films that became part of film history, like The Sixth Sense, Fight Club, and The Matrix, all of which left their footprint. Additionally, we had animated classics like Toy Story 2, Tarzan, and The Iron Giant. American auteurs like Stanley Kubrick, Martin Scorsese, Sofia Coppola, Spike Jonze, and Paul Thomas Anderson released important work. Comedy legends Adam Sandler and Eddie Murphy were doing hilarious work that audiences moved in droves to see. But also, the indie circuit produced cult hits like Office Space and Boondocks Saints. All in all, it’s easy to see why 1999 was such an iconic year for film. 1999 is a deep roster, ranging from all genres and voices, giving audiences such a wide variety of artful, popcorn fun.

Related: 10 Movies That Made 1994 an Iconic Year in Film

10 Star Wars Episode I: The Phantom Menace


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Sixteen years after Star Wars fans thought their beloved trilogy had ended, George Lucas decided to drop the prequels to the Luke Skywalker story. Not only generating enough excitement to earn over $1 billion at the global box office, but Star Wars: Episode I – The Phantom Menace also gave us the iconic Darth Maul, the controversial Jar-Jar Binks, and one of the greatest lightsaber duels in the history of the franchise between Darth, Qui-Gon Jinn, and Obi-Wan. The duel sets up the plight and arc of Obi-Wan as it intersects with the young Anakin before he turns into the formidable galactic villain, Darth Vader.

9 Office Space


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The cult hit of the 90s promptly entered the workplace comedy canon. Mike Judge makes perfect use of his workplace wit, humor, and seemingly nuanced look at the life of the middle-class worker. Whether it be the blue-collar in King of The Hill or here, the white-collar in Office Space. With memorable bits from every worker’s dream of smashing the faulty printer or the “I showed her my ‘Oh’ face.”. Judge’s sharp-eyed observations make Office Space a comedy classic during a year of cult hits.


8 Being John Malkovich


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An oddity of a Hollywood production that at the time almost felt novel. Being John Malkovich is an idea from the singular mind of Charlie Kaufman that was harnessed and digested by another warm-hearted weirdo Spike Jonze. With a concept built around finding a door that leads you inside the body and consciousness of famed actor John Malkovich, the film was a perfect bookend of surreal comedy to end the decade with an all-star ensemble led by John Cusack and Cameron Diaz.

7 The Iron Giant


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Despite not reaching a major audience upon its release, Brad Bird’s The Iron Giant has since garnered a cult following that properly elevated it to modern classic status. With a signature, hand-drawn animation style that blended in computer-generated effects as well, The Iron Giant managed to be a heartwarming story of friendship but also a high octane action-adventure. Director Brad Bird would bring this style to Pixar years later, but for now, The Iron Giant remains at the top of anyone’s list for all-time animated films.

Related: Popular Debut Movies From First-Time Filmmakers, Ranked

6 Eyes Wide Shut


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This would be the last film from the legendary director Stanley Kubrick, who teamed up with, at the time, the Hollywood power couple of Nicole Kidman and Tom Cruise. During a brief stint of time where Cruise still took cracks at his star power veneer, Eyes Wide Shut is a film that always pops up in conversation during the holidays. The film is a surreal drift into the shadows of a secret society and also a complex distillation of a marriage in crisis, where Cruise memorably wanders the dimly lit streets of New York. If you’re going to a party, don’t be afraid to whisper “Fidelio”.

5 10 Things I Hate About You


Heath Ledger and Julia Stiles point to the camera in 10 Things I Hate About You
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An all-timer in the Teen movie genre and an irresistible rom-com that elevated Heath Ledger to superstardom, 10 Things I Hate About You is another film from 1999 that you’d have trouble escaping today. Based on a classic Shakespeare play, the story is modernized to the world of high school class hierarchy. With Julia Stiles staving off the charming degeneracy of Heath Ledger with a supporting cast of Joseph Gordon-Levitt and David Krumholtz as the nerdy sidekicks, 10 Things has all the ingredients for formulaic comedy but raised in quality by such a charismatic cast. Especially the star-making moment of Ledger singing a classic love song in the middle of a football field.


4 The Sixth Sense


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The film that would go on to launch the career of the singular M. Night Shyamalan, a name would become synonymous with the phrase “twist ending.” The Sixth Sense would embody everything that people would go on to love about the director and his intricate work. A film with all the trappings of a supernatural thriller but wrapped with empathy and humanity. With an incredible twist ending that the pre-social-media world would not spoil, Sixth Sense became a smash, global success. Now, with the “I see dead people” line becoming one of the all-time greats, The Sixth Sense concretely became part of the culture.

3 The Blair Witch Project


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It’d be near impossible to repeat the hysteria and word-of-mouth phenomenon of The Blair Witch Project today because of social media. A film so terrifying (at the time) and marketed to the world as found footage, Blair Witch went on to shock the country. Put together on the meager budget of $200,000, Blair Witch went on to make $248.8 Million. Its legacy is everlasting and influence on the found-footage genre undeniable, spawning such carbon copies like Paranormal Activity or REC. While the film’s horror hasn’t aged well, it’s impossible not to talk about the year 1999 without mentioning just what a monocultural moment the film was for anyone going to the movies.

Related: 15 Best Found Footage Movies, Ranked

2 Fight Club


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David Fincher’s anti-social, chaos-inducing opus Fight Club is another film from 1999 that caught on late. The film failed, initially to ignite the fervor and acclaim it has garnered since its release. While maligned by some critics and failing to strike profit at the box office. But, true to the film’s nature, it caught on by word of mouth and was not an overnight success. With what is now considered an agent of chaos icon “Tyler Durden” and the “The first rule of Fight Club.”, David Fincher’s maddening and hypnotic wild ride of violence also led to one of the all-time great film twists while offering a message about consumerism with sustained relevance.

1 The Matrix


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There isn’t much else to say about The Matrix that hasn’t already been said. With the combination of sleek genre fair, immaculately cool set-pieces, and a high sci-fi concept executed to perfection by Lana and Lily Wachowski, The Matrix has lived in the minds of audiences everywhere since its release. The movie is designed with mind-bending special effects and the since popular “simulation theory” that has permeated the every day since the “Meta-verse” has started up. Even before seeing the film, the “bullet time” scene was known everywhere and has since been a staple of film culture. The Matrix is a rare cultural artifact that will remain perfect.


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