10 Must-Watch Movies from 1999, Ranked

1999 was the close of the century that saw the very beginnings of cinema through its rapid development and evolution. It was also the end of a decade that began with bold new independent voices in film and was host to innovative new technologies that would change the face of blockbuster cinema.

Staring down the barrel of Y2K seemed to embolden filmmakers and studios to create wholly original films along with radical adaptations of existing works. 1999 was a year filled with great movies that covered a wide swath of tones, voices and genres. Whether searching for stories that challenge or ones that simply seek to entertain, these ten films are among the best of the year and must be watched.

10

‘Office Space’ (1999)

Directed by Mike Judge

Office Space was the first live-action film by Beavis and Butthead creator Mike Judge. It’s a sharply written comedy that still accurately captures the American work life in an office setting perfectly over 25 years later. Judge’s biting satire of the day-to-day drudgery of mindless office drones pre-empted TV series like Judge’s own Silicon Valley and the highly acclaimed Severance. The film wasn’t a box office hit but found its audience on cable and the home video market, leading it to become a beloved cult classic.

Expanded from Judge’s earlier animated shorts titled Milton, and inspired by the director’s own work in an office, the movie stars Ron Livingston as Peter, a programmer at a software company who feels aimless and unfulfilled. That all changes when he goes to a hypnotherapist who unintentionally leaves Peter in a perpetual state of relaxation. He stops caring about work and does what he wants, which ironically only leads him to a promotion. Office Space is pointedly funny in its critiques and is filled with memorably quotable characters, played to perfection by its cast, including Gary Cole as the mundanely villainous boss Lumbergh, and Stephen Root as the timid, red stapler-loving Milton.

9

‘Galaxy Quest’ (1999)

Directed by Dean Parisot

Essential 90s sci-fi movie Galaxy Quest was inspired by the dedicated fandom of Star Trek, and tapped into the culture of conventions, online discourse and IP reboots years before those were part of the normal ecosystem of Hollywood and were still considered niche. Dean Parisot’s wickedly funny and wonderfully entertaining film is a perfectly cast adventure that is both retro and prescient at the same time.

Tim Allen stars as the Shatner-like lead of the titular long-since canceled sci-fi series. His co-stars include Sigourney Weaver as the buxom blonde bombshell of the series whose job solely consisted of repeating the computer and a scene-stealing Alan Rickman as a British thespian whose career has been reduced to repeating his character’s catchphrase for nerds. Their mundane lives are changed forever when a group of legitimate aliens beams the cast up, believing them to be a true space crew, to help them battle a nefarious nemesis. It’s Three Amigos by way of Gene Roddenberry and the film is entertaining from beginning to end with plenty of action, comedy and endlessly quotable lines.

8

‘Fight Club’ (1999)

Directed by David Fincher

Another 90s box office bomb that found its audience at home, David Fincher’s counter-culture Gen-X black comedy Fight Club focuses on thirty-something men who are part of a generation raised on advertising that rebel against the Baby Boomer culture through acts of violence. Naturally, those violent impulses lead to a toxic culture that quickly evolves into domestic terrorism.

Fincher’s film is filled with radical disdain for the prevailing popular culture of the time, but it also shows an alternative that is not a healthy substitute. Controversial upon its release and continually misinterpreted by film bros, Fight Club may be a product of its time but seems only more relevant in an era of rising incel subculture. The film is remembered for its trio of performances by Brad Pitt, Edward Norton and Helena Bonham Carter, as well as for Fincher’s strong visuals and the mid-film twist that turns the story on its head. It’s a must-watch movie that should inspire plenty of debate.

7

‘The Iron Giant’ (1999)

Directed by Brad Bird

Beautifully animated and heartwarming, Brad Bird’s animated adaptation of The Iron Giant brought the filmmaker boldly into the world of feature films. Despite being overlooked at the box office (a common theme among the films of 1999), The Iron Giant has only gained more appreciation as time has gone on, and has been rediscovered, as Bird became a household name thanks to animated hits like Ratatouille and The Incredibles.

Set in an idealized small town in the 1950s, young latchkey child Hogarth Hughes discovers the titular character having crash-landed near his home. The arrival of the massive alien robot inspires both Hogarth to come out of his shell as well as a suspicious government agent to investigate. With it’s mix of 2D and 3D animation, and terrific voice cast, The Iron Giant is as charming as animated films get.

6

‘Eyes Wide Shut’ (1999)

Directed by Stanley Kubrick

The final film from master filmmaker Stanley Kubrick, Eyes Wide Shut is an erotic thriller that was unjustly dismissed by audiences, as evidenced by its terrible Cinemascore grade, and some critics reacted coldly to it as well, comparing it unfavorably to Kubrick’s other masterworks. Time has shown that it’s another complex mystery from one of cinema’s most uncompromising auteurs.

Shot over a period of fifteen months on meticulously crafted sound stages in England (despite being set in New York City), the film follows the nightmarish journey of a doctor, played by Tom Cruise, who spirals into an exploration of eroticism after discovering his wife has harbored fantasies of being unfaithful. It’s an eerie examination of sexuality that like all of Kubrick’s work has a lot to digest and interpret through its layered visuals.

5

‘The Sixth Sense’ (1999)

Directed by M. Night Shymalan

Coming at the end of a decade that had plenty of definitive horror movies but that is also often viewed as being slimmer in its selection, M. Night Shymalan’s The Sixth Sense was a splash of cold water to the faces of audiences who felt burnt out on the glut of the slick but vapid slashers that came in the wake of the success of Scream.

Bruce Willis stars as a child psychologist who takes on a new patient, Haley Joel Osment in an Oscar-nominated role, who has the unique problem of being able to talk to the dead. The Sixth Sense is a beautifully crafted horror film that relies on atmosphere and the well-honed performances of its cast to provide the scares. The script slowly unfurls it’s mysteries and Shymalan’s shocking twist ending actually feels integral to the plot, unlike those in his later films that feel unnecessary or like a crutch for lazy writing.

4

‘The Matrix’ (1999)

Directed by The Wachowskis

Coming off their debut film, the erotic thriller film Bound, the Wachowski’s pushed the queer content into subtext but kept the neo-noir vibes for the cyberpunk action masterpiece The Matrix. The movie became an instant influence on the action and sci-fi genres, with its innovative bullet-time effects quickly infiltrating dozens of other action movies and becoming satirized in comedies.

Keanu Reeves plays Neo, a hacker who discovers that the world he inhabits is all a simulation, and that the real world is an apocalyptic wasteland where the remains of humanity fight against their oppressive machine overlords. The plot pulls from dozens of different sources, including anime and the works of writer William Gibson, and synthesizes it all into a slick, action-packed package that makes some of the entry-level philosophy course dialogue easy to digest. Essential and influential, The Matrix is much more than its imitators or empty sequels, and was one of the most significant films released in 1999.

3

‘Magnolia’ (1999)

Directed by Paul Thomas Anderson

Paul Thomas Anderson’s sprawling character drama Magnolia was his divisive follow-up to the acclaimed Boogie Nights. It follows one of the best movie casts of the 90s, as they search for connection and feeling in a world ruled by cruel fate. Anderson conducts his cast like an orchestra, each singular story fitting into the larger symphony of chaos that culminates in a biblical climax.

The cast is absolutely without fault, but special notice was given to Tom Cruise at the time for his performance as Frank Mackey, a misogynistic motivational speaker who uses his profession to cover up his own insecurities and past. It’s a role that weaponizes Cruise’s natural charisma for a toxic but vulnerable character. If Cruise hadn’t subsequently been swallowed whole by Scientology, it’s quite possible the intervening years between his amazing work in 1999 and his later full dedication to the Mission: Impossible franchise could’ve been filled with some very daring and interesting performances.

2

‘Being John Malkovich’ (1999)

Directed by Spike Jonze

From his influential music videos and short films, to his four feature-length classics, Spike Jonze has been one of the most unique directorial talents to grace the silver over the last few decades. He announced his entry into the mainstream with the fiercely original Being John Malkovich. Working off Charlie Kaufman’s surreal screenplay, Jonze crafted a dark comedy that has few true parallels.

John Cusack plays a puppeteer who gets a job on the seventh and a half floor of an office building where he discovers a doorway that leads into the mind of actor John Malkovich. From there the film goes into even more unexpected directions as more and more people enter Malkovich’s mind, until the actor himself is made aware of the portal’s existence. The cast is terrific, with Cameron Diaz and Catherine Keener in pivotal supporting roles, and Malkovich himself playing off his idiosyncratic reputation. In a year that was filled with sterling original films, Being John Malkovich is the most singular.

1

‘All About My Mother’ (1999)

Directed by Pedro Almodóvar

Pedro Almodóvar is a filmmaker who has consistently put out great work for over four decades that has certainly garnered awards attention and critical acclaim but remains frustratingly overlooked by American audiences. The Spanish filmmaker is known for his melodramas with bold visual styles that frequently feature LGBTQ+ and feminist themes, both of which are on full display in the film frequently cited as his best, All About My Mother.

After the death of her teenage son Esteban, Manuela (Cecilia Roth) travels to Barcelona to reconnect with the teen’s other parent, the transgender Lola (Toni Cantó). In Barcelona, she makes other connections, including Rosa (Penélope Cruz) a nun who is HIV positive and pregnant. It’s Almodóvar’s love letter to women, all women, and he tells his story with compassion and sincerity, all the while calling to mind the classic Hollywood melodramas of filmmakers like Douglas Sirk with his intense visual palette. All About My Mother is a film the likes of which is hardly seen in Hollywood, and should be watched for its empathetic storytelling of women whose lives are often reduced or overlooked in mainstream cinema.