The Best Movies From 1999

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Updated April 30, 2024 48.6K views 120 items
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Voting Rules
Only movies released in theaters in 1999.

Over 2,100 movie fans have come together to cast their votes for the best movies of 1999. From classic thrillers like The Sixth Sense and Fight Club, to irreverent comedies like American Pie and Office Space, this list has some of the most beloved films from that era.

The Matrix wowed audiences with its unique visuals and revolutionary action sequences while Toy Story 2 captivated kids and adults alike with its heartwarming story about friendship. Other classics include Being John Malkovich and its quirky look at identity issues and Election with its witty satire on high school politics.

Each one of these timeless films resonates with viewers today in different ways - whether it be through the heartfelt messages or all-star cast performances, they remain a treat for all ages. So why not take a trip down memory lane by voting up your favorite movies from 1999? It might just become someone else's new favorite movie.

Most divisive: Star Wars: Episode I - The Phantom Menace
Over 2.2K Ranker voters have come together to rank this list of The Best Movies From 1999
  • The Matrix
    1
    Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss
    1,363 votes

    An innovative blend of science fiction and action, The Matrix is a groundbreaking film that redefined genre cinema in 1999. Directed by Lana and Lilly Wachowski, this mind-bending story follows Neo (Keanu Reeves) as he uncovers the truth behind the simulated reality he inhabits - known as the Matrix - while leading a rebellion against oppressive machines controlling humanity. Boasting cutting-edge visual effects such as "bullet time" and providing thought-provoking philosophical concepts about existence itself, The Matrix has become a cornerstone of modern filmmaking revered by critics and fans alike.

  • The Sixth Sense
    2
    Bruce Willis, Haley Joel Osment, Toni Collette
    1,103 votes

    Renowned for its shocking twist ending, M. Night Shyamalan's The Sixth Sense is a supernatural thriller that captivated audiences in 1999 with its chilling atmosphere and exceptional performances. Starring Bruce Willis as child psychologist Dr. Malcolm Crowe and Haley Joel Osment as troubled young Cole Sear, the film follows their attempts to uncover the cause of Cole's terrifying visions of deceased individuals. Showcasing deft direction, masterful storytelling, and captivating cinematography, The Sixth Sense remains an influential piece of modern cinema that keeps viewers guessing until its unforgettable conclusion.

  • Fight Club
    3
    Brad Pitt, Ed Norton, Helena Bonham Carter
    1,355 votes

    Fight Club, a distinct and powerful film directed by David Fincher, premiered in 1999 to widespread acclaim. Based on Chuck Palahniuk's novel of the same name, the movie stars Brad Pitt and Edward Norton as two disillusioned men who form an underground fighting club as an aggressive form of male bonding and emancipation from societal norms. The film's themes of consumerism, masculinity, and self-destruction are expertly woven into its provocative narrative, making it one of the standout movies of 1999. With its shocking twist ending, superb performances from its cast, and relentless pacing, Fight Club remains a must-watch for cinephiles worldwide.

  • The Green Mile
    4
    Tom Hanks, David Morse, Michael Clarke Duncan
    1,018 votes

    Based on Stephen King's bestselling novel and directed by Frank Darabont in 1999, The Green Mile is an emotionally powerful drama that examines themes such as redemption and sacrifice via extraordinary events at a Louisiana death row prison during the Great Depression. Tom Hanks stars as compassionate prison guard Paul Edgecomb who forms an unlikely bond with gentle giant inmate John Coffey (Michael Clarke Duncan), whose miraculous healing powers have profound consequences for those around him. Featuring stellar performances from its ensemble cast—including Oscar-nominated turns by Hanks and Duncan—The Green Mile is essential viewing for those seeking a poignant and engaging cinematic experience.

  • The Mummy
    5
    Brendan Fraser, Rachel Weisz, John Hannah
    787 votes

    Bringing swashbuckling adventure and horror together in a thrilling package, Stephen Sommers' 1999 film The Mummy reinvigorated interest in Egyptology while delivering heart-pounding action sequences alongside chilling supernatural scares. Brendan Fraser stars as daring adventurer Rick O'Connell who, along with librarian Evelyn Carnahan (Rachel Weisz) and her brother Jonathan (John Hannah), inadvertently awakens ancient Egyptian priest Imhotep (Arnold Vosloo) from his cursed slumber leading to dire consequences for all involved. Encompassing romance, humor, and classic monster movie elements, The Mummy remains a beloved fan-favorite among action-adventure enthusiasts nearly two decades after its release.

  • Office Space
    6
    Ron Livingston, Jennifer Aniston, David Herman
    827 votes

    Office Space is a hilarious cult classic comedy directed by Mike Judge that delves into the soul-crushing monotony of corporate life through the eyes of beleaguered software engineer Peter Gibbons (Ron Livingston). Released in 1999, this witty satire lampoons office culture with relatable characters such as cubicle-dwelling everyman Milton Waddams (Stephen Root) and overbearing boss Bill Lumbergh (Gary Cole), showcasing the absurdity inherent within the daily grind for many employees worldwide. With its biting commentary on workplace frustrations and memorable quotes, Office Space endures as a compelling examination of the human condition within modern corporate America.

  • 10 Things I Hate About You
    7
    Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
    708 votes

    A modern-day retelling of William Shakespeare's The Taming of the Shrew, the 1999 romantic comedy 10 Things I Hate About You stars Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, and Larisa Oleynik in a charming tale of teenage relationships and high school politics. Directed by Gil Junger, this delightful film features witty dialogue, appealing performances from its young cast, and an infectious soundtrack that resonated with audiences during its release. With Ledger's memorable rendition of "Can't Take My Eyes Off You" and Stiles' poignant delivery of her titular poem, 10 Things I Hate About You remains an enduring classic for fans of '90s cinema.

  • American Beauty
    8
    Kevin Spacey, Annette Bening, Thora Birch
    1,007 votes

    Sam Mendes' directorial debut American Beauty is a powerful exploration of suburban ennui that earned five Academy Awards in 2000, including Best Picture. Kevin Spacey stars as Lester Burnham—a disillusioned advertising executive at the center of this darkly comedic family drama—who becomes infatuated with his teenage daughter's best friend (Mena Suvari) while simultaneously struggling with his crumbling marriage (Annette Bening). Showcasing masterful writing by Alan Ball and stellar performances from its ensemble cast, American Beauty expertly dissects themes such as materialism, self-discovery, and societal expectations amid a seemingly idyllic suburban landscape.

  • Cruel Intentions
    9
    Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon
    508 votes

    Cruel Intentions is a deliciously dark teen drama released in 1999, loosely based on Pierre Choderlos de Laclos' novel Les Liaisons dangereuses. Directed by Roger Kumble and starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair in career-defining roles, this sensual tale explores themes such as betrayal, manipulation, and self-discovery amid a backdrop of decadent New York City high society. Featuring sumptuous cinematography and a seductive soundtrack boasting hits such as The Verve's "Bitter Sweet Symphony," Cruel Intentions offers viewers a titillating glimpse into the twisted machinations of privileged adolescence.

  • Sleepy Hollow
    10
    Johnny Depp, Christina Ricci, Miranda Richardson
    712 votes

    Tim Burton's 1999 film adaptation of Washington Irving's classic tale The Legend of Sleepy Hollow, Sleepy Hollow stars Johnny Depp as Ichabod Crane, a New York City constable sent to investigate mysterious beheadings in the eponymous small town. With its atmospheric visuals, macabre Gothic aesthetic, and grisly horror sequences featuring Christopher Walken as the dreaded Headless Horseman, this stylish production is a delightfully spooky ride for fans of supernatural thrillers. Boasting unforgettable set designs and captivating performances from its ensemble cast—including Christina Ricci as love interest Katrina Van Tassel—Sleepy Hollow demonstrates why it ranks among Tim Burton’s most beloved cinematic endeavors.

  • South Park: Bigger, Longer & Uncut
    11
    George Clooney, Minnie Driver, Isaac Hayes
    556 votes

    From the irreverent minds behind the popular animated television series South Park comes South Park: Bigger, Longer & Uncut—a raunchy musical extravaganza that pushes boundaries with its biting satire and controversial humor. Released in 1999, this film co-directed by Trey Parker and Matt Stone sees the titular Colorado town embroiled in a dangerous conflict with Canada after parents blame their neighbors to the north for their children's exposure to profanity-laden entertainment. Featuring an Academy Award-nominated song ("Blame Canada") and a plethora of memorable musical numbers such as "Uncle F**ka" and "Kyle's Mom's a B***h," South Park: Bigger, Longer & Uncut remains an audacious achievement in animated satire.

  • Being John Malkovich
    12
    John Cusack, Cameron Diaz, Catherine Keener
    718 votes

    Spike Jonze's 1999 directorial debut Being John Malkovich is a surreal exploration of identity that introduced audiences to one of the most inventive cinematic minds in recent memory. Written by Charlie Kaufman, this mind-bending tale stars John Cusack as puppeteer Craig Schwartz who stumbles upon a portal leading into the mind of actor John Malkovich (playing himself), allowing individuals to inhabit his consciousness for brief periods. As Schwartz exploits this discovery for personal gain alongside his manipulative co-worker (Catherine Keener) and wife (Cameron Diaz), Being John Malkovich offers viewers a kaleidoscope of existential concepts deftly woven into an engaging narrative.

  • The Iron Giant
    13
    Jennifer Aniston, Eli Marienthal, Harry Connick
    684 votes

    The Iron Giant premiered in 1999 to widespread acclaim for its heartwarming story about friendship between young Hogarth Hughes (Eli Marienthal) and an extraterrestrial robot who crash-lands near his small Maine town amid Cold War tensions. Directed by Brad Bird before his subsequent work on Pixar classics such as The Incredibles and Ratatouille, this animated film boasts a touching narrative, impressive visuals, and memorable voice performances from talents like Jennifer Aniston, Harry Connick Jr., and Vin Diesel. Earning praise for its themes of empathy, acceptance, and the importance of choosing one's path in life, The Iron Giant remains an enduring family favorite.

  • Austin Powers: The Spy Who Shagged Me
    14
    Mike Myers, Heather Graham, Michael York
    720 votes

    In 1999, audiences were once again treated to the groovy exploits of British secret agent Austin Powers in Austin Powers: The Spy Who Shagged Me. Directed by Jay Roach and starring Mike Myers in multiple roles—including both titular character Austin and his nemesis Dr. Evil—this uproarious sequel continues the madcap adventures of everyone's favorite swinging spy as he travels back in time to recover his stolen mojo. With quotable lines, outrageous costumes, and unforgettable characters such as Mini-Me (Verne Troyer) and Felicity Shagwell (Heather Graham), this comedy sequel remains a beloved entry in the Austin Powers franchise.

  • Galaxy Quest
    15
    Tim Allen, Sigourney Weaver, Alan Rickman
    585 votes

    Galaxy Quest is a sci-fi comedy released in 1999 that lovingly parodies popular television series like Star Trek while maintaining its unique identity as an entertaining standalone film. Directed by Dean Parisot and featuring an ensemble cast including Tim Allen, Sigourney Weaver, Alan Rickman, Tony Shalhoub, Sam Rockwell, and Daryl Mitchell, this delightful romp follows former television space opera actors who are whisked away by aliens seeking their assistance against a deadly threat. Packed with witty humor, thrilling action sequences, and affectionate nods to genre tropes, Galaxy Quest has become a cult classic among fans of science fiction cinema.

  • Girl, Interrupted
    16
    Winona Ryder, Angelina Jolie, Clea Duvall
    471 votes

    Based on Susanna Kaysen's eponymous memoir, Girl, Interrupted is a compelling drama released in 1999 that features standout performances from Winona Ryder and Angelina Jolie—who won her first Academy Award for her role as sociopath Lisa Rowe. Directed by James Mangold, this film explores themes such as mental illness, self-discovery, and personal growth through the eyes of Kaysen (Ryder) during her stay at a psychiatric hospital during the late 1960s. Showcasing powerful acting alongside poignant storytelling grounded in real-life experiences, Girl, Interrupted offers viewers an intimate glimpse into the often misunderstood world of mental health treatment.

  • American Pie
    17
    Jason Biggs, Shannon Elizabeth, Alyson Hannigan
    825 votes

    A quintessential coming-of-age comedy, American Pie burst onto screens in 1999 with its raunchy humor and endearing portrayal of teenage friendship. Directed by brothers Paul and Chris Weitz, this crowd-pleasing tale follows a group of high school friends—played by Jason Biggs, Chris Klein, Thomas Ian Nicholas, Eddie Kaye Thomas, and Seann William Scott—as they make a pact to lose their virginity on prom night. Featuring memorable scenes involving warm apple pastries and uproarious one-liners from characters such as Jim's Dad (Eugene Levy), American Pie has become a beloved classic within the teen-comedy genre.

  • The Talented Mr. Ripley
    18
    Matt Damon, Gwyneth Paltrow, Jude Law
    606 votes

    Based on Patricia Highsmith's novel, The Talented Mr. Ripley is a psychological thriller released in 1999 that features exceptional performances from its star-studded cast including Matt Damon, Jude Law, Gwyneth Paltrow, Cate Blanchett, and Philip Seymour Hoffman. Directed by Anthony Minghella, this tense narrative follows the exploits of enigmatic Tom Ripley (Damon) as he becomes entangled in the lives of wealthy expatriates Dickie Greenleaf (Law) and his girlfriend Marge Sherwood (Paltrow) in 1950s Italy—leading to disastrous consequences for all involved. With its lush cinematography capturing picturesque settings and remarkable acting conveying nuanced characterizations, The Talented Mr. Ripley remains a gripping tale about ambition, obsession, and deception.

  • The Boondock Saints
    19
    Willem Dafoe, Sean Patrick Flanery, Norman Reedus
    542 votes

    In 1999 director Troy Duffy made his feature debut with The Boondock Saints—a gritty action-thriller that attained cult status for its stylish violence, dark humor, and unconventional storytelling. Starring Sean Patrick Flanery and Norman Reedus as two Irish brothers who embark on a vigilante mission to rid Boston of evil under the guidance of their religious beliefs, this film showcases memorable performances from Willem Dafoe as an eccentric FBI agent hot on their trail. With its catchy dialogue and unforgettable action sequences, The Boondock Saints remains a beloved fixture within the realm of crime cinema.

  • Dogma
    20
    Ben Affleck, Linda Fiorentino, Matt Damon
    591 votes

    Kevin Smith's irreverent take on religious dogma and organized faith manifested itself in his controversial 1999 film Dogma—a comedy that explores complex theological concepts through humor without forsaking sincerity or thoughtfulness. Boasting an all-star cast including Ben Affleck, Matt Damon, Chris Rock, Salma Hayek, Jason Lee, Alan Rickman, Linda Fiorentino—and the director himself reprising his role as Silent Bob—Dogma pokes fun at conventional biblical lore while examining more profound ideas about belief systems and devotion. Despite inciting backlash from certain religious groups upon its release due to perceived blasphemy, Dogma endures as an influential examination into matters of faith within contemporary cinema.

  • Double Jeopardy
    21
    Tommy Lee Jones, Ashley Judd, Bruce Greenwood
    369 votes

    Double Jeopardy is a suspenseful crime thriller directed by Bruce Beresford that premiered in 1999 to audience acclaim for its engaging plot twists and standout performances by Ashley Judd and Tommy Lee Jones. Judd stars as Libby Parsons—a woman framed for her husband's murder—who discovers he is still alive upon her release from prison and resolves to exact justice without fear of further legal repercussions due to the titular legal concept preventing her from being tried twice for the same crime. Showcasing atmospheric cinematography and a tense cat-and-mouse narrative, Double Jeopardy remains an enthralling cinematic experience that keeps viewers on their toes.

  • Varsity Blues
    22
    James Van Der Beek, Jon Voight, Paul Walker
    429 votes

    Varsity Blues is a 1999 sports drama directed by Brian Robbins that delves into the world of high school football culture within small-town Texas amid intense pressure for players to achieve success on the field at any cost. Starring James Van Der Beek as Jonathan "Mox" Moxon—a backup quarterback thrust into the spotlight following an injury to the team's star player—the film examines themes such as loyalty, courage under adversity, and the importance of maintaining integrity amid conflicting influences. With memorable performances from actors like Jon Voight and Paul Walker, Varsity Blues resonates with audiences as a compelling portrayal of contemporary American sports culture.

  • Magnolia
    23
    Jason Robards, Julianne Moore, Tom Cruise
    591 votes

    Paul Thomas Anderson's sprawling ensemble drama Magnolia premiered in 1999 to critical acclaim for its interwoven narratives exploring themes such as forgiveness, redemption, love amid loss—all set during one rainy day within California's San Fernando Valley region. Boasting an incredible cast including Tom Cruise, Julianne Moore, Philip Seymour Hoffman, William H. Macy, John C. Reilly, and Jason Robards in his final role before passing away—Cruise received an Academy Award nomination for his portrayal of self-help guru Frank T.J. Mackey. With its poignant storytelling featuring emotionally charged scenes set to a captivating score by Jon Brion, Magnolia remains a powerful examination of human connections within the fabric of everyday life.

  • Big Daddy
    24
    Adam Sandler, Joey Lauren Adams, Jon Stewart
    572 votes

    Adam Sandler stars as the lovable but irresponsible Sonny Koufax in Big Daddy—a heartwarming comedy released in 1999 about an unlikely father-son bond forged through unexpected circumstances. Directed by Dennis Dugan and featuring supporting roles from Joey Lauren Adams, Jon Stewart, Rob Schneider, and Steve Buscemi, this film follows Sonny as he learns valuable life lessons while caring for abandoned five-year-old Julian (Cole and Dylan Sprouse). With its mix of slapstick humor and genuine emotion showcasing Sandler's versatility as a comedic actor, Big Daddy has resonated with audiences as a charming exploration of parenthood and personal growth.

  • Payback
    25
    Mel Gibson, Gregg Henry, Maria Bello
    324 votes

    Payback is a gritty crime-thriller directed by Brian Helgeland that hit theaters in 1999 starring Mel Gibson as Porter—an anti-hero seeking vengeance against his former partner-in-crime Val Resnick (Gregg Henry) and crime syndicate boss Bronson (Kris Kristofferson) after they betray him during a heist gone awry. With shades of film noir permeating its dark atmosphere alongside sharp dialogue and brutal action sequences, Payback offers viewers an unrelenting tale of revenge featuring standout performances from Gibson as well as supporting roles played by Maria Bello, David Paymer, Bill Duke, and Lucy Liu.

  • The Bone Collector
    26
    Denzel Washington, Angelina Jolie, Queen Latifah
    356 votes

    Directed by Phillip Noyce in 1999, The Bone Collector is an engrossing thriller starring Denzel Washington as quadriplegic forensics expert Lincoln Rhyme tasked with solving a series of grisly murders inspired by obscure crime novels alongside rookie cop Amelia Donaghy (Angelina Jolie). As they work together to decipher cryptic clues left at each crime scene while forging an unlikely bond amid harrowing circumstances, Washington and Jolie deliver top-notch performances punctuating the film's tension-fueled atmosphere. The Bone Collector remains an exciting entry within the crime-thriller genre for its captivating premise and skilled execution.

  • Three Kings
    27
    George Clooney, Mark Wahlberg, Ice Cube
    550 votes

    A unique blend of war film and heist thriller, Three Kings arrived in theaters in 1999 under the direction of David O. Russell—offering viewers an engaging look at the aftermath of the Persian Gulf War as four American soldiers (George Clooney, Mark Wahlberg, Ice Cube, and Spike Jonze) embark upon a risky mission to steal gold bullion hidden by Saddam Hussein's regime. With its distinctive visual style characterized by high-contrast color grading and whip-fast editing that adds to the film's frenetic pacing alongside memorable performances from its ensemble cast conveying the complexities inherent within wartime moral dilemmas—the movie stands out as one of Russell's most accomplished works during his early career.

  • Eyes Wide Shut
    28
    Tom Cruise, Nicole Kidman, Sydney Pollack
    594 votes

    Stanley Kubrick's final film before his untimely passing in 1999, Eyes Wide Shut is a provocative drama that examines themes of sexual desire, infidelity, and societal decadence through the eyes of Dr. Bill Harford (Tom Cruise) following his wife Alice's (Nicole Kidman) revelation of an intimate fantasy involving another man. As Bill embarks upon a dangerous journey into New York City's elite underworld of secret societies and hedonistic pleasures, Kubrick explores the dark recesses of human nature with masterful precision while employing visually arresting cinematography set against a haunting musical score composed by Jocelyn Pook. A controversial and polarizing piece upon release, Eyes Wide Shut remains an enigmatic cinematic masterpiece that continues to generate discussion among scholars and cinephiles alike.

  • The Hurricane
    29
    Denzel Washington, Vicellous Reon Shannon, Deborah Kara Unger
    364 votes

    The Hurricane is a biographical sports drama directed by Norman Jewison in 1999 that tells the inspiring true story of Rubin "Hurricane" Carter—the professional boxer wrongfully convicted of triple homicide in 1966—and his subsequent quest for justice amidst racial prejudice and judicial corruption. Denzel Washington delivers a powerhouse performance as Carter which earned him an Academy Award nomination for Best Actor while showcasing themes such as perseverance against adversity, the impact of grassroots activism led by supporters Lesra Martin (Vicellous Reon Shannon) and Sam Chaiton (Liev Schreiber), and the transformative power of forgiveness within a flawed legal system.

  • The Blair Witch Project
    30
    Heather Donahue, Michael C. Williams, Joshua Leonard
    548 votes

    The Blair Witch Project is a revolutionary found-footage horror film that debuted in 1999 under the direction of Daniel Myrick and Eduardo Sánchez—contributing to the rise of viral marketing campaigns while leaving audiences terrified upon release due to its ambiguously authentic nature. Presented as a documentary-style account of three student filmmakers lost within Maryland's Black Hills Forest while investigating local legends surrounding purported supernatural occurrences involving a malevolent witch figure, this low-budget production capitalized on its unsettling atmosphere achieved through minimalistic techniques such as handheld camera work and improvised dialogue among its cast. The Blair Witch Project remains a landmark achievement within independent cinema that spawned countless imitations thanks to its innovative approach to storytelling.