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:
Years before Marvel made “cinematic universes” a thing, Kevin Smith was already doing it with his “ViewAskewniverse.” If Clerks. is his Iron Man, then Dogma is his Avengers: Endgame, not because it’s the last film set in his movie world, but because it’s the most ambitious.
Dogma is a blasphemous stew that pokes unrelentingly at Catholicism, but it works on its own as a comic fantasy unlike just about anything else to hit the screen. What really sells it, of course, is the cast Smith was able to assemble, from his longtime buddy (and the other half of Jay and Silent Bob) Jason Mewes to classically Shakespearean-trained Alan Rickman; from Matt Damon and Ben Affleck (hot off their Oscar wins for Good Will Hunting) to Mexican bombshell Salma Hayek; from motor-mouthed comic Chris Rock to rock goddess Alanis Morissette.
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
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
One of a couple of films on this list that truly is unlike any other movie, Being John Malkovich is a startlingly original debut for both its first-time feature director, Spike Jonze, and its first-time feature screenwriter, Charlie Kaufman. It’s a film whose very essence demands all suspension of disbelief, but it works beautifully, twist after harebrained twist. Kaufman’s literal head-trip of a script begins with a simple enough premise: a puppeteer (John Cusack) falls in love with a woman (Oscar-nominated Catherine Keener) who his not his wife (a nigh-unrecognizable Cameron Diaz). When he discovers a portal that leads directly into the brain of another human being, he finds a way to act on his desires with no repercussions… until there are.
At the center of it all is the actor whose name is not only above the title, but in the title, as John Malkovich plays an absurdist version of himself that truly must be seen to be believed. Never was another actor considered for the role of the man who has other human beings inhabiting his subconscious, if only because no other star’s last name could possibly be as fun to say. “Malkovich, Malkovich, 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
If you ask a group of critics what the toughest accomplishments in cinema are, one of the top answers will be attempting to create a sequel as good or better than its predecessor. There are some notable though not universally-agreed-upon examples, like Terminator 2: Judgment Day, Aliens, The Dark Knight, The Empire Strikes Back, and Best Picture winners The Return of the King and The Godfather Part II. And with Pixar’s first stab at a sequel, Toy Story 2 certainly entered the conversation. Shockingly, the movie was almost pushed directly to home video. With a tight schedule and a re-work of the script, John Lasseter and crew managed not only to churn out another critical success, but the movie also nabbed third place at the worldwide box office.
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
The world of cinematic Stephen King adaptations is full of schlock, but there are a few notable films that rise to the top, like Carrie, The Shining, and It. The Green Mile is one of the best of them. Returning to a prison setting not unlike the one from his first of his King adaptations, The Shawshank Redemption, writer/director Frank Darabont creates an exceedingly faithful adaptation in which all of King’s ambitious “serial novel” is represented, with one or two minor tweaks that only make the film better.
The true highlight of this film is its casting. Every actor breathes life into their character, from the guards — Tom Hanks’ world-weary Paul Edgecomb and David Morse’s steadfast Brutus Howell — to the inmates like Michael Jeter’s skittish Eduard Delacroix and Sam Rockwell’s feisty “Wild Bill” Wharton. The standouts, though, are Michael Clarke Duncan’s Oscar-nominated turn as the soulful John Coffey, who turns this death row cell block on its ear, and Doug Hutchison’s utterly vile Percy Whetmore, the abusive new guard who very easily makes my shortlist of movie villains I love to hate.
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
Among Hollywood’s most well-known directors, M. Night Shyamalan has famously experienced a controversial, up-and-down career. But before he became known for his signature style that leaves audiences and critics divided to this day, Shyamalan burst onto the scene in 1999 with one of the most iconic horror movies of all time: The Sixth Sense. At just 29 years old, Shyamalan stamped his name in the record books as the bone-chilling film became the years’s second highest grossing movie domestically behind Star Wars Episode I: The Phantom Menace, and the highest grossing horror film of all time, a mark it would hold for 18 years.
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
American Beauty remains one of the most misunderstood films of 1999. The divisive reactions to Sam Mendes’ suburban satire masterpiece speak to this. To many, the movie’s prestige drama reputation makes the film’s heightened reality and moments of showy reflection, like Wes Bentley gazing forlornly at a plastic shopping bag blowing in the wind, feel pretentious. Yet this is part of Mendes’s purpose; in addition to commenting on suburban angst from the perspective of both parents and children, American Beauty also satirizes the techniques of prestige dramas and simultaneously leans into them. It’s the kind of winking, knowing film Rian Johnson might have made. It is humorous throughout, using Kevin Spacey and Annette Bening’s fantastic comic timing to deliver a bevy of hilarious moments. Mendes takes prototypical dramatic characters and cuts them down to size, emphasizing their quirks with smirking criticism while masterfully eliciting sympathy for their self-selected plights. Chris Cooper’s military dad struggling with his sexuality feels like a trope, yet Mendes takes it to the next level with a heightened scene in the pouring rain that lampoons the conceit of the moment yet still allows Cooper’s authentic performance to draw you in. American Beauty plays with the tropes of Oscar-bait dramas and uses them to craft a sneakily funny story of unease and dissatisfaction that is more memorable than most of its imitators and predecessors. – Connor
- Global rank: 197
- Wins 58% of matchups
- 865 users have it at #1
- 13,061 have it in their top 20
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
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
“You are not a beautiful and unique snowflake. You are the same decaying organic matter as everything else.”
Whether or not you buy into Fight Club’s nihilistic worldview, one thing is for certain: there have been no other movie like this. To be sure, pretenders have come and gone, feeling cool for riffing on their perception of this movie’s aesthetic. Yet this is a singular vision. From Jeff Cronenweth’s grimy cinematography to The Dust Brothers’ unsettling earworm of a score to the yin and yang of Brad Pitt and Edward Norton’s blistering performances, it’s an anarchic symphony of a film that could only have come from one conductor, David Fincher. No matter how many Se7ens or Social Networks he creates, Fight Club will always be his dystopian magnum opus.
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
These films don’t make the global Top Ten list for the year, but our bloggers feel they are worth your time.
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
Ask a group of Trekkies what their favorite Star Trek film is, and of course you’ll get some votes for The Wrath of Khan, but a disproportionate number of them may just tell you that the best Star Trek movie is not a Star Trek movie at all: Galaxy Quest is a pure love letter to the granddaddy of science fiction franchises, a loving spoof that succeeds because it reveres Trek in the form where it truly flourished: on the small screen.
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
Seeing a film in IMAX in 1999 was a very different experience to what it is today. Back then, IMAX theaters were rare, and they all had truly gigantic screens. The one I visited to see Fantasia 2000 was 60 x 80 feet, projected with 70mm film. This was before digital cinema was widespread. The feeling of being completed immersed in the colors, the sound, the music, and the animation was and still is one of the most exciting and exhilarating moments I’ve ever had watching a movie. It’s the one and only time I’ve gone twice to see the same film in IMAX.
Not only was the presentation of the highest quality, but the film itself was a superb mix of well-known selections, classical “hidden gems,” a “remaster” of an old favorite, and one of the last bastions of hand-drawn, 2D feature film animation to grace cinemas.
From the abstract take on Beethoven, to a dramatic and intense depiction of Stravinsky’s “Firebird,” to flying whales set to Respighi, to the Hirschfeld-inspired backdrop for “Rhapsody In Blue,” there’s so much variety and care put into this film. It’s a shame that it is seemingly forgotten and hasn’t received the reverence it deserved.
If you want to remind yourself how powerful great animation and music can be together, do yourself a favor and watch Fantasia 2000
on the largest screen possible. Put down your phone, give it your full attention, and get enraptured like I did. It’s on Disney+
, so fire up your giant 4K TV and spend 75 minutes with an overlooked masterpiece. – Nathan Chase
Is your favorite film from 1999 represented on the list? Is there some glaring omission? Let us know in the comments, and rank all movies from 1999 on your own Flickchart to influence the global chart.