Sometimes, just sometimes, the stars just align and make for a legendary year, like 1984 for the NBA Draft, or the 1982 vintage for Bordeaux. In film, 1999 is widely considered to be the best year in movies, and it’s hard to disagree. There are probably some better top-heavy years, but the turn of the century gave us unrivaled depth and breadth of great films. Interestingly, many of the year’s greatest films were initial box office disappointments, slow burners of innovative storytelling that generally met with middling box office results but grew by word-of-mouth into veritable cult classics and cinematic landmarks. Another common thread among all these films (even in ones that aren’t listed here, like The Blair Witch Project and Audition) is a tendency to push the boundaries, whether it be in form, themes, narrative, special effects, or redefining tropes/genres. Here are my personal favorites from that remarkable year, 20 years on:
Honorable Mentions
American Beauty; 10 Things I Hate About You; The Talented Mr. Ripley; Lock, Stock and Two Smoking Barrels; Magnolia; Office Space; Toy Story 2
10. Galaxy Quest
Directed by Dean Parisot; starring Tim Allen, Sigourney Weaver, Alan Rickman
I’m sure I’d love this movie even more if I were actually a trekkie (or was even more familiar with Star Trek), but it’s a testament to how culturally ubiquitous Star Trek is and how piercingly funny and relatable Galaxy Quest is that I laughed as much as I did while watching this. The story follows a cast of actors on a popular Star-Trek like TV show who encounter real aliens (who in turn think they are real space explorers), and the line between what’s real and what’s made up quickly and hilariously gets blurred and hijinks ensue. One of the best movie parodies of all time, Galaxy Quest boasts a deep bench (Alan Rickman is perfect, but I had almost forgotten that Sam Rockwell, Justin Long and even Rainn Wilson were in this) and a shamelessly audacious sense of humor, poking fun at TV tropes and cliches galore. It has the rare achievement of being loved and validated by Star Trek fans but equally admired by mainstream audiences who enjoy high quality comedy. By Grabthar’s hammer, this movie is fun to watch.
9. The Insider
Directed by Michael Mann; starring Al Pacino, Russell Crowe
The Insider is a movie that simmers throughout its entire 2 hr and 37 min runtime, always threatening to boil over at any moment. It’s Michael Mann at his best, with Pacino seething in a righteous rage, but much more restrained than he is compared to previous Michael Mann films. The female roles are pretty underbaked, but the story and characters are delicate but thrilling. Journalistic exposé movies can be talky and tedious, but Mann infuses this comparatively quiet film with a vibrant sense of psychology and emotion. One of the best things about The Insider is that it paints an underdog story without being campy or melodramatic, and portrays the struggle against big tobacco without being preachy or moralizing. It’s rare indeed to come across a film about “doing the right thing” which humanizes, rather than lionizes, its protagonists. It’s a movie that knows how hard it is to do the right thing and examines what it costs, even after a “win” – it is not about the confrontation, but rather the consequences.
8. The Iron Giant
Directed by Brad Bird; starring Vin Diesel, Jennifer Aniston, Harry Connick Jr.
This cold war era animated classic is Brad Bird at his most endearing and heart-tugging best, telling the story of, as Bird himself put it, “What if a gun had a soul, and didn’t want to be a gun?” At first glance, a kid + pet/robot buddy cartoon film seems pretty standard, but the development of the characters and relationships and the themes of mortality, existentialism, big government are all injected with a sense of honesty and humanity that is touching if you have a heart (even a metal one). There’s a level of authenticity in the characters and their relationships that effectively underlines the anti-war or anti-violence sentiment but lets the story speak for itself. Vin Diesel does some great voice work here and the animation style is appropriately nostalgic, but The Iron Giant is a classic in every sense of the word – it is just as resonant and affecting today as it was 20 years ago.
7. Being John Malkovich
Directed by Spike Jonze; starring John Cusack, Cameron Diaz, Catherine Keener, John Malkovich
Being John Malkovich introduced us to the talents of Spike Jonze and of Charlie Kaufman, and what a bow this is. It’s a typically bizarre fantasy-comedy from Kaufman, absurd while still being fun and chock full of pop culture references. Jonze deftly digs into the strangeness of human desires in the most quirky, out-of-the-box ways. John Cusack and Cameron Diaz are two sad sack characters who hate their lives (in such sharp left turns from their usual roles) who discover a way to, for just 15 minutes, disappear into the body of John Malkovich and literally be somebody else, but Catherine Keener is the real star turn here, while John Malkovich is endlessly watchable in his puppet/puppeteer role. This surreal escapist film is intelligent, weird, funny, captivating, and full of ideas.
6. Eyes Wide Shut
Directed by Stanley Kubrick; starring Tom Cruise, Nicole Kidman
Kubrick’s final film is a slow-paced, taxing experience, but in the best way possible. That’s evident even in its production – the film holds the Guiness World Record for longest continuous film shoot at 400 days – though not completely surprising for the notoriously perfectionist Kubrick, who purposely even created strain and jealousy between Kidman and Cruise, a real life couple at the time. That sexual tension, the sense of helplessness and failure, the strange nighttime (and daytime) encounters – like everything else in Kubrick’s films, it all remains completely intentional throughout the entire dreamscape/fantasy sequence that makes up most of the movie. Eyes Wide Shut delves into the planting and growing of the seeds of jealousy in a relationship, and though it is far from Kubrick’s best work, this is a great example of his range and skillful exploration of sexual fantasy, jealousy, power structures, of complacency and ignorance.
5. All About My Mother
Directed by Pedro Almodovar; starring Cecilia Roth, Penelope Cruz, Marisa Paredes
Winner of the Best Foreign Film at the Academy Awards, Pedro Almodovar’s All About My Mother is somehow still grossly overlooked. The director’s signature use of color and style, and symbolic use of literature (A Streetcar Named Desire plays a huge part in this movie) are all evident here, but it remains smart while not pretentious. The film is oddly paced and very quickly doesn’t go where you expect it to, but it’s a beautiful story about actions and unintended consequences. What does being a mother mean? We see it a little in Pain and Glory but it’s fully fleshed out here – to care for someone and to be cared for, in ways we see played out in all the literal and figurative mother-child roles. The material is emotionally sophisticated with a real aptitude for flair, and the various parental relationships are so human. It’s also a tribute to womanhood, such that almost all of the characters – even the male ones – are women! Even better, each one is more memorable than the last. This is a richly satisfying film on every level.
4. Fight Club
Directed by David Fincher; starring Edward Norton, Brad Pitt, Helena Bonham Carter
It’s hard to overstate just how impactful this film was and still is for a whole generation of teenage boys. As a freshman in high school, I met a schoolmate who, in my very first conversation with me, told me about drugs, girls, and making napalm from simple household items. His god was Tyler Durden. He ended up failing and getting kicked out of school later that semester, but that was the cultural impact that this adaptation of the chuck Palahniuk had. Sure, there was American Psycho, The Dark Knight, and Memento, but there was nothing quite like Fight Club. Forget even” the first rule of Fight Club is… “, how many times, as you cross the aisle/pew, have you heard/thought “ass or crotch”? The machismo, the overwhelming sense of gritty coolness, the burning image of shirtless Brad Pitt. Viewed through a 2019 lens, it’s admittedly problematic in a lot of ways and reeks of toxic masculinity, but its underlying power isn’t lost as the Narrator (and the audience) tries to reckon with the anticonsumerist, anticapitalist philosophy before veering headlong into pure terrorism. Fight Club is subversive, anarchic, conspiratorial, and it plumbs the depths of the male psyche in groundbreaking ways – there is no movie from 1999 that is both more cult and more classic.
3. The Road Home
Directed by Zhang Yimou; starring Zhang Ziyi, Sun Honglei
Zhang Yimou is an all-time visually brilliant film director, but watching films like The Road Home kind of makes you wish that he made more smaller scale/low stakes films like this one, channeling his sublime sense of imagery into conveying specific emotions; early to mid career Yimou had a real tenderness that’s all but disappeared in his later work. The Road Home opens with a man returning home to his countryside village from the city when he finds out his father has passed away. Shot in dreary black and white, the story bursts out in vibrant colors once he starts to recount the story of how his mother and father first met and fell in love. It’s as poetic and personal as anything Yimou has ever made. Zhang Ziyi also makes her film debut here and is an absolute revelation – she is impossibly young and energetic and lights up the screen. There is so little dialogue throughout (it’s mostly voiceover), but all the little touches – the authentic village setting, carrying food in little porcelain bowls, the passing seasons – help shape this story that’s in the running for one of my favorite romantic films of all time. The film captures both the rush of the stolen glances of young love as well as the faithfulness and nostalgia of a lifelong love, and Yimou masterfully weaves themes of tradition, grief and education into the emotional fabric of this masterwork.
2. Election
Directed by Alexander Payne; starring Matthew Broderick, Reese Witherspoon, Chris Klein
Alexander Payne is a gifted director and Election is my favorite film of his by some margin. I didn’t quite get it the first time I saw it (I was probably too young), but Election is one of the movies I most love to rewatch and to reference – two surefire signs of greatness. The story follows well-liked high school history teacher Jim McAllister (played by Matthew Broderick) who, after a series of events, decides to interfere with the high school presidential election to defeat the smug overachiever Tracy Flick (Reese Witherspoon). The movie is so wickedly funny and smart satire (I think it was one of the first films I saw where I had to recognize the dissonance between the voiceover and what was actually appearing onscreen), and it is stylistically so fun and unforgettable, from the freeze frames to the flashbacks to the voiceovers. Broderick, Chris Klein and Jessica Campbell are all impeccable, but Reese Witherspoon is so damn perfect here that “Tracy Flick” isn’t just an iconic movie character, it’s become a generic descriptor for an ambitious female know-it-all gunner. Election says a lot about politics and society, and deals with sexual repression and suburban frustration in a much more entertaining and interesting way than its fellow 1999 release American Beauty, and is one of the greatest and most unique films about high school life or about politics ever made.
1. The Matrix
Directed by the Wachowskis; starring Keanu Reeves, Carrie Anne Moss, Laurence Fishburne
It feels a little silly to try to write anything about The Matrix at this point. What hasn’t already been said, written, discussed, analyzed? It so completely revolutionized not only action movies, but the landscape of film in general. The Matrix is really a groundbreaking action/sci fi/superhero origin story mashup with heavy manga influences. Watching this movie for the first time completely blew my mind and smashed open my world view. It’s like encountering Shakespeare, or falling in love for the first time. There are probably three movies that defined my childhood in each of its various stages – Fantasia, Terminator 2, and then The Matrix. I saw The Matrix on a plane 20 years ago and immediately rewatched it 2-3 more times on that plane ride. Looking back, it’s not quite as philosophically complex as my 12-year-old self thought it was, and there are definitely a few campy lines of dialogue that belong squarely in the province of 90s action movies (Joey Pantoliano in particular is such a movie villain), but it was just so damn cool. As evidence of its staying power, The Matrix spawned countless iconic movie lines (“I know kung fu”, “There is no spoon”, “guns, lots of guns”) and memes and pop culture references (the red pill/blue pill, the John Woo style double gun action, the sunglasses and leather coats that redefined cool) and the endless parodies and knockoffs with bullet time and gunfu. It’s The Matrix‘s world, and we are all just living in it.
