The Top 10 Films of 1999
As this decade draws to a close, Flickchart looks back 20 years to the close of a century and a millennium. We’re talking about the year that Napster and SpongeBob Squarepants became a thing, the Euro was created as a currency, and Vladimir Putin became president of Russia. The world was gripped by the fear of Y2K, but modern cinema was having a pretty banner year, as you can see below.
These are the Top 10 Films of 1999, as ranked by the users of Flickchart:
10. Dogma
And that’s not counting George Carlin, Jason Lee’s manic angel of death, or a monster literally made from human excrement. Did I mention this movie’s weird? Sure it is, and it could easily be dismissed as heretical garbage, but Smith’s cast helps him sell it, and we’re still talking about it twenty years later. – Nigel Druitt
- Global rank: 629
- Wins 48% of matchups
- 361 users have it at #1
- 7714 have it in their top 20
9. Magnolia
Paul Thomas Anderson had announced his prowess to the world loudly with Hard Eight and Boogie Nights. Paying homage to his favorite directors was prevalent in his early work, and Magnolia sees PTA ape Robert Altman. A sprawling three hour epic with interspersed storylines, Magnolia might be PTA’s most humanist work. While there is plenty of awful behavior throughout, he ultimately ends the film with notes of hope on the universal experiences of humanity. With a fantastic Aimee Mann-inspired soundtrack and a huge ensemble of powerful actors ranging from Tom Cruise to Julieanne Moore, Anderson weaved one of his most potent works yet. It may not be to everyone’s taste, but it was an early sign of why PTA was destined to become one of the preeminent filmmakers of his generation. – Connor Adamson
- Global rank: 572
- Wins 51% of matchups
- 272 users have it at #1
- 3331 have it in their top 20
8. Being John Malkovich
By agreeing to take on the very mantle of the film itself, John Malkovich became destined for notoriety: career suicide if the movie tanked, celluloid immortality if it worked. Fortunately, he picked the perfect film. May his name live forever in infamy. – Nigel
- Global rank: 406
- Wins 52% of matchups
- 410 users have it at #1
- 7787 have it in their top 20
7. Toy Story 2
The sequel to the movie that started it all for Pixar saw the return of the entire A-list cast including Tom Hanks and Tim Allen, as well as newcomers Joan Cusack, Kelsey Grammer, and Wayne Knight. Like its predecessor, the sequel deals with surprisingly deep themes as Woody struggles with an existential dilemma. The animation is sleeker than before, the music from Randy Newman is splendid, and of course the humor is top-notch for all ages. If the Oscar for Best Animated Feature Film had existed at the time, it would have surely been a front-runner alongside Disney’s Tarzan and Brad Bird’s The Iron Giant, and it could have kickstarted Pixar’s unprecedented run of awards season success even earlier. You’d be hard-pressed to find a series more charming than Toy Story, as its nearly impossible to watch this fun-loving group of toys without a giant grin on your face. – Kyle Larkin
- Global rank: 301
- Wins 54% of matchups
- 680 users have it at #1
- 13,471 have it in their top 20
6. The Green Mile
It’s all highlighted by a typically gorgeous Thomas Newman score and amazing photography from cinematographer David Tattersall. And never before or since Mr. Jingles has a movie managed to make me care so deeply for a simple mouse. – Nigel
- Global rank: 259
- Wins 57% of matchups
- 636 users have it at #1
- 11,388 have it in their top 20
5. The Sixth Sense
It is difficult to find many faults, if any, in The Sixth Sense, as everything from the writing to the acting to the “haunting” score by James Newton Howard is top-notch. Haley Joel Osment delivers what could easily be considered a top-ten performance from a child actor. Toni Collette shines as the tortured mother on the brink of despair, and Bruce Willis is as proficient as ever as the naive child psychologist. With a multi-layered plot that ponders dark themes, it’s hard to avoid gripping a pillow tightly or averting your eyes during the movie’s many thrilling scenes. The Sixth Sense also created one of the horror genre’s most famous one-liners: “I see dead people.” And, of course, its ending contains the twist of all twists, which to this day remains unparalleled, despite Shyamalan’s best efforts. – Kyle
- Global rank: 239
- Wins 56% of matchups
- 588 users have it at #1
- 12,319 have it in their top 20
4. American Beauty
- Global rank: 197
- Wins 58% of matchups
- 865 users have it at #1
- 13,061 have it in their top 20
3. Office Space
Before Michael Scott’s office and Leslie Knope’s parks and recreation department came to dominate the American office comedy market, we had this little late-90s number based on the Milton shorts from SNL. Colorful and quotable, Office Space strikes a chord by tapping into how many of us feel about menial office work and making us laugh at it, as Preston Sturges had done in similar movies decades earlier. Whether it is the eccentricities of Stephen Root’s Milton, Gary Cole’s apathetic Lumbergh, or Ron Livingston’s everyman protagonist, the characters of Office Space give the film relatability and staying power. Through them we live out many of the angry fantasies that intrude into office workers’ minds then and now, and in catharsis we find something cheerier than anger. It shouldn’t be surprising the film comes from Mike Judge, one of the best deadpan character comedy minds out there. By the way, get off of this movie site on your work time and get us those TPS reports, m’kay? Great, thanks. – Connor
- Global rank: 145
- Wins 61% of matchups
- 600 users have it at #1
- 11,517 have it in their top 20
2. The Matrix
Red pill or blue pill. Kung-fu. Slow motion. Keanu Reeves. The Matrix is a defining film not only of 1999, but of a decade. Emerging from the morass of 90s cynicism, this dark and influential sci-fi action work took some basic philosophical ideas and infused them with a “neo” cyber-punk flavor. The idea of waking up from a lie is now thoroughly ingrained in the pop culture conscious as memes proliferate about “the simulation.” As a work of cinema, The Matrix‘s unique visual style has inspired countless copycats as well. The underdog tale at the heart of the story keeps the movie honest and helped cement Reeves’ status as an action icon. The Matrix reminds us to live life with our eyes wide open. – Connor
- Global rank: 41
- Wins 70% of matchups
- 1763 users have it at #1
- 22,846 have it in their top 20
1. Fight Club
Cinephiles have been breaking the first rule of Fight Club for twenty years now, and they’re not about to stop any time soon. – Nigel
- Global rank: 11
- Wins 75% of matchups
- 2575 users have it at #1
- 25,419 have it in their top 20
Bloggers’ Picks
These films don’t make the global Top Ten list for the year, but our bloggers feel they are worth your time.
The Straight Story
Before David Lynch’s surrealist masterpiece Mulholland Dr., there was his most down-to-earth film, The Straight Story. It’s in the title, after all; Lynch wanted to make a film with a straightforward narrative and teamed up with Disney, of all studios, to make it. The story is still somewhat bizarre, though: an elderly man rides a lawnmower across several states to reconcile with his dying brother. The movie is based on a real-life story, and the out-there quality of it must have appealed to Lynch, who gives us a heartwarming feature anchored in a fantastic end-of-career turn from Richard Farnsworth. Farnsworth conveys the down-home quality of his character and his simple drive to do what he feels is right. Farnsworth was dying during the filming and committed suicide the year after release. He only agreed to do the role out of admiration for the real-life Alvin Straight, and this admiration is clear in the performance. Lynch, of course, adds some of his own directorial touches, with deliberate zooms and pans and his trademark ambient sound design. The film is therefore distinctly Lynchian in style, but that style is married to a wholesome story of family and community. A bright spark of hope in a year of cynicism. The Straight Story is one of the best of 1999. – Connor Adamson
Galaxy Quest
Not that this is a movie made only for a specific subset of sci-fi fans. Galaxy Quest is, at its core, a whimsical, lighthearted showbiz comedy, with just the right amount of pathos to put some meat on the funny bones. It’s populated by a cast at the top of their games and having the time of their lives, none more so than the late Alan Rickman, whose pitch-perfect turn as a weary thespian in funny alien makeup gives Galaxy Quest its Trek-appropriate Shakespearean soul. – Nigel Druitt
1999 was such an amazing year for movies, you could write a book on the subject. In fact, somebody has!
https://www.amazon.ca/Best-Movie-Year-Ever-Screen/dp/1501175386
Favourites of mine missing here include:
Ghost Dog: Way of the Samurai
The Ninth Gate
Election
Ravenous
Eyes Wide Shut
The Virgin Suicides
The Talented Mr. Ripley
Honourable Mentions:
The Limey
The Insider
Man on the Moon
eXistenZ
South Park: Bigger, Longer, & Uncut