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 greatest years for cinema. 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 Martin Scorsese, Stanley Kubrick, Sofia Coppola, Spike Jonze, and Paul Thomas Anderson released important work that year. Comedy legends Adam Sandler and Eddie Murphy were doing hilarious work that audiences moved in droves to see. But also, the indie circuit produced ’90s cult classic hits like Office Space and Boondocks Saints.
Updated November 7th, 2022: This article has been updated with additional films as well as more details regarding each movie on the list including how a few opened on the same day.
The reason for all this is unclear. Did everyone just think Y2K was a real thing and everyone just put out great work in what they thought would be their last chance? Probably not but there was something in the air that made the offerings of 1999 unique, versatile, and enduring which has made it such an iconic year for film. 1999 is a deep roster, ranging from all genres and voices, giving audiences a wide variety of artful, popcorn fun. Here are the 12 best movies that show just how great the last year of the 20th century was for film.
Star Wars Episode I: The Phantom Menace
20th Century Fox
Sixteen years after Star Wars fans thought their beloved trilogy had ended, George Lucas released the first installment in the prequel trilogy. If there was one movie that could be called the event of 1999 it was easily Star Wars: Episode I - The Phantom Menace. Not only generating enough excitement to earn over $1 billion at the global box office, but the movie also gave audiences 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.
There is no doubt that The Phantom Menace was a controversial movie at the time of its release, and in many ways set a new paradigm for online discussion regarding franchise properties both for good and ill. Yet nobody can doubt that in 1999, it was impossible to escape Star Wars fever.
Office Space
20th Century Studios
This 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.”
Office Space bombed at the box office, partially due to a terrible marketing campaign, but the film quickly found new life on home video and became a staple of television airings on networks like TBS and Comedy Central. Judge’s sharp-eyed observations make Office Space a comedy classic during a year of cult hits.
Fight Club
Director David Fincher’s antisocial, chaos-inducing opus Fight Club is another film from 1999 that caught on late. The film initially failed 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 it was speaking to a similar disdain for the modern comforts of the world as other 1999 films like Office Space and American Beauty.
But, true to the film’s nature, it caught on by word of mouth through home video sales. 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 and the emptiness of fascist movements with sustained relevance.
Toy Story 2
Walt Disney Studios Motion Pictures
Toy Story 2 is a miracle movie. Originally intended as a direct-to-video sequel, the film was upgraded to theatrical release only to have the filmmakers scrap half the movie to rework it to get the project on par with the first Toy Story. On top of that, they almost lost all the footage when a Pixar employee accidentally deleted everything, only to be saved when an employee who took her work home with her on maternity leave had a backup file.
Toy Story 2 not only lived up to everyone’s expectations but surpassed them and is often regarded as one of the greatest sequels ever made. It helped set the template for future Pixar films, being fun family films with a real emotional heart that could make any grown-up cry. The 2000s were a golden decade for Pixar, and it all kicked off with Toy Story 2.
Being John Malkovich
USA Films
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.
Eyes Wide Shut
Warner Bros.
This would be the last film from the legendary director Stanley Kubrick, who teamed up with, at the time, the Hollywood power couple Nicole Kidman and Tom Cruise. During a brief stint of time when 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."
Magnolia
New Line Cinema
Cruise had an incredible year in 1999, with both Eyes Wide Shut and Magnolia, director Paul Thomas Anderson’s follow-up to Boogie Nights. Magnolia is an ensemble film that deals with various characters in interconnected stories that deal with happiness, regret, and forgiveness. The film’s climax is of biblical proportions that both engrossed and turned off audiences at the time. All these years later, Magnolia remains a marvel of a film and an indicator of just the type of talent Paul Thomas Anderson was as a filmmaker.
The Iron Giant
Warner Bros. Pictures
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 of all-time animated films.
The Sixth Sense
Buena Vista Pictures
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.
This is just how stacked of a year 1999 was for movies. The Sixth Sense and The Iron Giant, two iconic films opened on the same day with The Sixth Sense taking the number one spot while Iron Giant sadly bombed at number nine.
The Blair Witch Project
Haxan Films
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 a meager budget of $200,000, Blair Witch went on to make $248.8 million.
Its legacy is everlasting and its influence on the found-footage genre is undeniable, spawning such carbon copies like Paranormal Activity or REC. On top of that, it opened so close to The Sixth Sense and played in theaters at the same time showing just how powerful and versatile the horror genre could be. 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.
10 Things I Hate About You
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 I Hate About You has all the ingredients for formulaic comedy but raised in quality by such a charismatic cast that has endured for over 20 years. The moment of Ledger sang “I Want You Baby” was a star-making moment for the young actor and is one of those iconic film moments. 10 Things I Hate About You also has the distinction of opening the same day as the next film on this list and still managed to become a hit despite being in the shadows of The Matrix.
The Matrix
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 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.
Released a whole month before The Phantom Menace, nobody could have predicted this original film would become the iconic action movie of the year and would redefine how action movies were made for the following decade. The Matrix in many ways feels like the perfect film to close out the 90s and lead into the 2000s. The Matrix is a rare cultural artifact that will remain perfect.
