The Best Movies From 1999
- 1Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss
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.
- 2Brad Pitt, Ed Norton, Helena Bonham Carter
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.
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- 3Bruce Willis, Haley Joel Osment, Toni Collette
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.
More The Sixth Sense - 4Tom Hanks, David Morse, Michael Clarke Duncan
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.
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- 5Ron Livingston, Jennifer Aniston, David Herman
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.
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- 6Brendan Fraser, Rachel Weisz, John Hannah
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.
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- 7Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
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.
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- 8Kevin Spacey, Annette Bening, Thora Birch
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.
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- 9Johnny Depp, Christina Ricci, Miranda Richardson
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.
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- 10Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon
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.
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- 11Jennifer Aniston, Eli Marienthal, Harry Connick
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.
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- 12Tim Allen, Sigourney Weaver, Alan Rickman
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.
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- 13John Cusack, Cameron Diaz, Catherine Keener
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.
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- 14Mike Myers, Heather Graham, Michael York
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.
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- 15George Clooney, Minnie Driver, Isaac Hayes
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.
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- 16Jason Biggs, Shannon Elizabeth, Alyson Hannigan
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.
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- 17Matt Damon, Gwyneth Paltrow, Jude Law
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.
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- 18Winona Ryder, Angelina Jolie, Clea Duvall
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.
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- 19Ben Affleck, Linda Fiorentino, Matt Damon
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.
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- 20James Van Der Beek, Jon Voight, Paul Walker
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.
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- 21Willem Dafoe, Sean Patrick Flanery, Norman Reedus
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.
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- 22Tommy Lee Jones, Ashley Judd, Bruce Greenwood
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.
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- 23Jason Robards, Julianne Moore, Tom Cruise
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.
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- 24Tom Cruise, Nicole Kidman, Sydney Pollack
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.
- 25Adam Sandler, Joey Lauren Adams, Jon Stewart
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.
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- 26Denzel Washington, Vicellous Reon Shannon, Deborah Kara Unger
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.
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- 27Mel Gibson, Gregg Henry, Maria Bello
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.
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- 28Denzel Washington, Angelina Jolie, Queen Latifah
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.
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- 29Tony Goldwyn, Glenn Close, Minnie Driver
Disney's animated adaptation of Edgar Rice Burroughs' iconic character Tarzan premiered in 1999 to widespread acclaim for its stunning visual effects—particularly regarding fluid character motion achieved via groundbreaking computer-generated imagery combined with traditional hand-drawn animation techniques under directors Chris Buck and Kevin Lima. Featuring memorable songs by Phil Collins—including the Academy Award-winning "You'll Be in My Heart"—this heartwarming tale chronicles Tarzan's journey from orphaned infant raised by gorillas within the African jungle to discovering his true heritage as an English nobleman while navigating relationships with newfound love interest Jane Porter (voiced by Minnie Driver) and protective gorilla mother Kala (Glenn Close). With its rousing narrative, engaging characters, and breathtaking visuals set amidst lush jungle environments, Tarzan remains a beloved entry within Disney's animated canon.
- 30George Clooney, Mark Wahlberg, Ice Cube
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.
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- 31Matthew Broderick, Reese Witherspoon, Chris Klein
Alexander Payne's satirical comedy Election hit theaters in 1999, offering a biting look at high school politics and personal ambition through the eyes of ambitious overachiever Tracy Flick (Reese Witherspoon) as she vies for student body president against affable underdog Paul Metzler (Chris Klein) under the watchful eye of disillusioned teacher Jim McAllister (Matthew Broderick). With its razor-sharp screenplay, well-developed characters, and standout performances—particularly from Witherspoon in her breakout role—Election provided audiences with a hilarious glimpse into the cutthroat world of adolescent power struggles while proving itself a timeless classic within the genre.
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- 32Al Pacino, Russell Crowe, Christopher PlummerThe Insider is a stirring drama-thriller, directed by Michael Mann. It tells the story of Jeffrey Wigand (Russell Crowe), a tobacco industry executive-turned-whistleblower, and Lowell Bergman (Al Pacino), a seasoned producer for CBS's '60 Minutes.' The narrative unfolds as Wigand risks his safety to expose corporate deception, while Bergman grapples with journalistic ethics amidst corporate pressure. The film, noted for its gripping exploration of power dynamics and moral dilemmas, won several awards, including an Academy Award nomination for Best Picture. Its tense atmosphere and powerful performances make it a standout in its genre.More The Insider
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- 33Heather Donahue, Michael C. Williams, Joshua Leonard
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.
- 34Jim Carrey, Bob Zmuda, Max Alexander
Milos Forman directed this compelling biopic Man on the Moon in 1999 which delves into the enigmatic life and career of legendary comedic performer Andy Kaufman through an extraordinary portrayal by Jim Carrey that garnered critical acclaim for its uncanny accuracy. Chronicling Kaufman's breakthrough as Latka Gravas on television sitcom Taxi alongside his controversial wrestling antics and mysterious behavior that blurred the lines between reality and performance art, Man on the Moon offers viewers an intimate look at one of entertainment's most intriguing figures while questioning conventional notions surrounding fame and artistic integrity within popular culture.
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- 35Thomas Jane, Saffron Burrows, Samuel L. Jackson
Deep Blue Sea is a thrilling shark-infested action-horror film released in 1999 under the direction of Renny Harlin. The movie stars Saffron Burrows, Thomas Jane, LL Cool J, Michael Rapaport, Stellan Skarsgård, and Samuel L. Jackson as a team of researchers stationed at an underwater facility who find themselves fighting for their lives when their experiments on genetically enhanced mako sharks take a catastrophic turn. Featuring intense action sequences bolstered by innovative animatronics and CGI effects for its time—as well as memorable scenes such as Jackson's shocking mid-speech demise—Deep Blue Sea remains a suspenseful cinematic experience for fans of shark-infested mayhem.
More Deep Blue Sea - 36Robert De Niro, Billy Crystal, Lisa Kudrow
A delightful fusion of mobster movie tropes and comedic elements, Analyze This premiered in 1999 under director Harold Ramis as an entertaining romp featuring standout performances from Robert De Niro as mafia boss Paul Vitti who seeks therapy from mild-mannered psychiatrist Ben Sobol (Billy Crystal) to address his newly discovered anxiety issues. With its amusing premise offering a fresh take on the gangster film genre alongside sharp dialogue that highlights the comedic chemistry between De Niro and Crystal, Analyze This struck a chord with audiences and critics alike—proving itself a memorable entry within both actors' esteemed careers.
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- 37Jake Gyllenhaal, Chris Cooper, Laura Dern
Inspired by the true story of NASA engineer Homer Hickam, October Sky is a heartwarming drama released in 1999 that chronicles one young man's pursuit of his dream to become a rocket scientist despite facing seemingly insurmountable odds growing up in rural West Virginia amid socioeconomic hardship. Directed by Joe Johnston and starring Jake Gyllenhaal, Chris Cooper, Laura Dern, and Chris Owen, this uplifting tale showcases themes such as perseverance, self-determination, and the importance of supportive educators as it follows Hickam's journey from aspiring miner to accomplished aerospace engineer thanks to his unwavering passion for knowledge. Featuring stellar performances and an inspiring narrative grounded in real-life events, October Sky stands as a testament to the power of dreams and determination.
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- 38Al Pacino, Cameron Diaz, Dennis QuaidAny Given Sunday, a sports drama directed by Oliver Stone, is an intense exploration of the professional football world. The narrative orbits Tony D'Amato (Al Pacino), a veteran coach grappling with personal and professional crises and Willie Beamen (Jamie Foxx), a third-string quarterback who rises to fame amidst team turmoil. The film probes the tumultuous dynamics of sports politics, media scrutiny, and the personal sacrifices made in pursuit of glory. It's a visceral depiction of life on and off the field, layered with compelling performances that earned Foxx an MTV Movie Award for Best Breakthrough Performance.More Any Given Sunday
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- 39Brendan Fraser, Alicia Silverstone, Christopher Walken
Released in 1999, Blast from the Past is a charming romantic comedy directed by Hugh Wilson that offers a humorous look at culture shock and adapting to new surroundings when faced with unfamiliar experiences. Starring Brendan Fraser as Adam Webber—a young man who has spent his entire life living in an underground fallout shelter built by his paranoid father (Christopher Walken) during the height of Cold War panic—he emerges into present-day Los Angeles seeking supplies and unwittingly falls for quirky antique store owner Eve (Alicia Silverstone). With delightful performances from Fraser and Silverstone alongside an amusing premise exploring societal norms through fresh eyes, Blast from the Past is a lighthearted cinematic treat.
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- 40Hilary Swank, Chloë Sevigny, Peter Sarsgaard
Boys Don't Cry is a powerful drama based on the real-life story of Brandon Teena—a transgender man who was brutally murdered in Nebraska during December 1993 after his biological gender was revealed to acquaintances. Directed by Kimberly Peirce, this 1999 film features a career-defining performance by Hilary Swank in her Academy Award-winning role as Teena alongside strong supporting turns from Chloë Sevigny and Peter Sarsgaard. With its unflinching portrayal of violence against transgender individuals rooted in ignorance and prejudice, Boys Don't Cry offers an important glimpse into the struggles faced by those who defy societal norms in search of acceptance and love.
More Boys Don't Cry- #2 of 16 onIFC Films Movies List
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- 41Tobey Maguire, Charlize Theron, Delroy Lindo
Based on John Irving's novel and directed by Lasse Hallström in 1999, The Cider House Rules is a coming-of-age drama set during World War II that garnered critical acclaim for its sensitive exploration of complex themes such as self-discovery, love amid adversity, and moral ambiguity. Tobey Maguire stars as Homer Wells—an orphan raised within a rural Maine hospital who embarks upon his own path after forming a bond with a young couple (Charlize Theron and Paul Rudd)—while learning valuable life lessons from the institution's compassionate head doctor (Michael Caine) who imparts wisdom regarding the titular rules of the cider house. With its evocative storytelling, moving performances—Caine earned an Academy Award for his role—and picturesque cinematography that captures the beauty of its New England setting, The Cider House Rules remains a thought-provoking entry within contemporary cinema.
- #194 of 375 onThe Best Movies Based On Books
- #288 of 379 onThe Best Movies Of The '90s, Ranked
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- 42Pierce Brosnan, Rene Russo, Denis Leary
In 1999, director John McTiernan helmed this stylish remake of the 1968 film The Thomas Crown Affair—starring Pierce Brosnan as debonair billionaire and art thief Thomas Crown alongside Rene Russo as cunning insurance investigator Catherine Banning. As these two formidable adversaries engage in a high-stakes cat-and-mouse game filled with thrilling heist sequences, luxurious settings, and undeniable chemistry that culminates in a passionate romance—the movie offers viewers an enticing blend of suspense, glamour, and intrigue that has since solidified its place among classic caper films.
- #261 of 379 onThe Best Movies Of The '90s, Ranked
- #199 of 228 onThe 200+ Best Film Scores Of All Time
- #4 of 15 on15 Great Movie Heists That Were Planned To Perfection
- 43Antonio Banderas, Diane Venora, Dennis StorhøiIn The 13th Warrior, Ahmad Ibn Fadlan (Antonio Banderas), an Arab courtier, finds himself thrust into a world of Norse warriors and unknown dangers. When he's enlisted as the 13th member of a Viking party, he embarks on a mission to combat an unseen enemy terrorizing a distant village. Directed by John McTiernan, this action-adventure flick weaves elements of historical fiction and mythology. The film is based on Michael Crichton's novel Eaters of the Dead, providing a unique spin on the classic Beowulf tale. As Ahmad faces cultural clashes and brutal battles, his survival instincts are tested in ways unimaginable.More The 13th Warrior
- #696 of 769 onThe Most Rewatchable Movies
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- #60 of 200 onThe 195+ Greatest Adventure Movies
- 44James Woods, Kathleen Turner, Kirsten Dunst
Sofia Coppola's directorial debut The Virgin Suicides premiered in 1999, offering a haunting exploration of adolescence and suburban ennui through the eyes of five teenage sisters who succumb to inexplicable acts of self-destruction amid a seemingly idyllic environment. Based on Jeffrey Eugenides' novel and starring Kirsten Dunst, James Woods, Kathleen Turner, and Josh Hartnett among its talented cast, this ethereal drama features evocative cinematography that captures the dreamlike quality of its narrative alongside a mesmerizing score by French duo Air—contributing to an overall atmosphere of melancholic beauty that has resonated with audiences for decades.
More The Virgin Suicides- #49 of 133 onThe Most Utterly Depressing Movies Ever Made
- #39 of 63 onThe Greatest Directorial Debuts Of All Time
- #363 of 473 onThe 400+ Best Chick Flicks Ever
- 45Bill Pullman, Bridget Fonda, Oliver Platt
A tongue-in-cheek homage to classic monster movies, Lake Placid debuted in 1999 as an entertaining creature-feature directed by Steve Miner that pits humans against nature in the form of a giant crocodile lurking within an idyllic Maine lake. Starring Bill Pullman, Bridget Fonda, Oliver Platt, Brendan Gleeson, and Betty White among its eclectic cast, this thrilling romp balances humor and horror while showcasing impressive special effects for its time. Despite receiving mixed reviews upon release due in part to its intentionally campy tone, Lake Placid has since gained cult status among fans who appreciate its cheeky approach to the genre.
More Lake Placid- #139 of 149 onMovies That Should Never Be Remade
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- 46Milla Jovovich, John Malkovich, Faye Dunaway
Luc Besson directed this historical epic The Messenger: The Story of Joan of Arc in 1999 which chronicles the life and legacy of France's patron saint through a powerful performance by Milla Jovovich in the titular role. Featuring an impressive supporting cast including John Malkovich, Faye Dunaway, and Dustin Hoffman as well as lavish production design that immerses viewers within medieval Europe during times of brutal conflict—the film offers a visually arresting look at one of history's most revered figures. Although met with mixed reviews upon release, The Messenger: The Story of Joan of Arc remains a compelling entry within the historical drama genre that showcases Besson's signature flair for grandiose storytelling.
- #148 of 262 onThe 200+ Best War Movies Of All Time
- #237 of 425 onThe Greatest Movies in World Cinema History
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- 47Freddie Prinze, Rachael Leigh Cook, Matthew Lillard
She's All That is a delightful romantic comedy directed by Robert Iscove that captured the hearts of audiences in 1999. Starring Freddie Prinze Jr., Rachael Leigh Cook, Paul Walker, and Matthew Lillard, this modern-day Pygmalion retelling follows popular high school jock Zack Siler (Prinze Jr.) as he attempts to transform artsy outsider Laney Boggs (Cook) into prom queen material through an ill-conceived bet with fellow classmates. Boasting an infectious '90s soundtrack and memorable dance sequences choreographed by Fatima Robinson alongside endearing performances from its talented cast, She's All That remains a beloved staple for fans of teen romantic comedies.
More She's All That- #250 of 379 onThe Best Movies Of The '90s, Ranked
- #31 of 473 onThe 400+ Best Chick Flicks Ever
- #38 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- 48Johnny Depp, Frank Langella, Lena Olin
The Ninth Gate is a supernatural thriller directed by Roman Polanski that premiered in 1999 starring Johnny Depp as rare book dealer Dean Corso, who becomes embroiled in a dangerous quest to locate the titular demonic tome capable of summoning Satan himself. As Corso travels throughout Europe while encountering mysterious figures both human and otherworldly, The Ninth Gate showcases atmospheric cinematography that evokes classic horror cinema aesthetics through its shadowy visuals and eerie score composed by Wojciech Kilar. Though polarizing among audiences upon release due to its slow-burning narrative and unconventional conclusion, The Ninth Gate remains an intriguing entry within the realm of occult-themed cinema for viewers seeking a more cerebral exploration into matters of sacred texts and arcane knowledge.
More The Ninth Gate- #475 of 769 onThe Most Rewatchable Movies
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- 49Desmond Askew, Taye Diggs, William FichtnerGrocery store clerk Simon (Desmond Askew) occasionally sells drugs from his cash register at work, so when soap opera actors Adam (Scott Wolf) and Zack (Jay Mohr) come looking for Ecstasy on a quiet Christmas Eve, they are surprised to find Ronna (Sarah Polley) covering his shift. Desperate for money, Ronna decides to become an impromptu drug dealer, unaware that Adam and Zack are secretly working for obsessed narcotics officer Burke (William Fichtner).More Go
- #480 of 633 onThe 600+ Funniest Movies Of All Time
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- 50Kevin Bacon, Kathryn Erbe, Illeana Douglas
Kevin Bacon stars in Stir of Echoes—a chilling supernatural thriller directed by David Koepp in 1999 about a blue-collar worker who becomes haunted by terrifying visions following an ill-fated hypnosis session that unlocks his latent psychic abilities. As Tom Witzky (Bacon) delves deeper into the mystery surrounding his newfound gift while navigating his crumbling marriage and friendships amid increasingly disturbing encounters with malevolent forces—this film provides audiences with a gripping narrative filled with unexpected twists and expertly crafted scares that will keep them on the edge of their seats until its shocking conclusion.
More Stir of Echoes- #38 of 252 onThe 200+ Best Psychological Thrillers Of All Time
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- 51Liam Neeson, Ewan McGregor, Natalie PortmanIn Star Wars Episode I: The Phantom Menace, a young slave boy named Anakin Skywalker (Jake Lloyd), possessing extraordinary piloting skills, is discovered on the desert planet Tatooine by two Jedi Knights, Qui-Gon Jinn (Liam Neeson) and his apprentice Obi-Wan Kenobi (Ewan McGregor). Concurrently, the malevolent Sith Lord Darth Maul (Ray Park) poses a dark threat, while Queen Amidala of Naboo (Natalie Portman) fights to save her people. This science fiction epic, directed by George Lucas, marked the beginning of the legendary Star Wars prequel trilogy, introducing new characters and deepening the saga's lore. Notable for its groundbreaking special effects and John Williams's iconic score, it won Saturn Awards for Best Costumes and Best Special Effects.
- 52Hank Azaria, Janeane Garofalo, William H. Macy
In 1999, director Kinka Usher brought a new breed of superhero to the big screen with Mystery Men—a quirky comedy based on Bob Burden's comic book series starring Ben Stiller, Janeane Garofalo, Hank Azaria, William H. Macy, and Paul Reubens as an eclectic group of would-be crimefighters who must save their city from nefarious villain Casanova Frankenstein (Geoffrey Rush). Showcasing inventive visual effects, colorful characters with unique abilities such as "Furious" (Stiller), who channels his anger into fighting prowess and "The Shoveler" (Macy), who wields shovels like martial arts weapons—this film offers viewers an offbeat alternative to traditional superhero fare while providing plenty of laughs along the way.
More Mystery Men- #456 of 705 onThe All-Time Greatest Comedy Films
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- 53Richard Farnsworth, Sissy Spacek, Jane Galloway HeitzA retired farmer and widower in his 70s, Alvin Straight (Richard Farnsworth) learns one day that his distant brother Lyle (Harry Dean Stanton) has suffered a stroke and may not recover. Alvin is determined to make things right with Lyle while he still can, but his brother lives in Wisconsin, while Alvin is stuck in Iowa with no car and no driver's license. Then he hits on the idea of making the trip on his old lawnmower, thus beginning a picturesque and at times deeply spiritual odyssey.More The Straight Story
- #361 of 675 onThe Best Movies Roger Ebert Gave Four Stars
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- #18 of 28 onThe Best Movies Where Nothing Really Happens
- 54Sean Connery, Catherine Zeta-Jones, Ving Rhames
Released in 1999, Entrapment is a suspenseful heist film directed by Jon Amiel that stars Sean Connery and Catherine Zeta-Jones as skilled thieves who become embroiled in a dangerous partnership while attempting to pull off the ultimate crime. With its exotic locations, thrilling action sequences—including an unforgettable laser-dodging scene—and palpable chemistry between its two charismatic leads, this movie offers audiences an exciting ride filled with twists and turns that keep viewers guessing until the final reveal. Despite receiving mixed reviews upon release, Entrapment has since garnered appreciation for its entertaining blend of romance and intrigue within the realm of high-stakes art theft.
- 55Devon Sawa, Seth Green, Elden HensonWhen slacker teen Anton Tobias (Devon Sawa) has his right hand possessed by a demonic force, he finds that his life gets a lot more interesting. While Anton himself is an amiable guy, his hand proves to be an appendage of death, killing his two best buddies, Pnub (Elden Henson) and Mick (Seth Green), who return to life as wisecracking zombies. In addition to murdering those closest to him, Anton's evil hand significantly hinders his chances with lovely neighbor Molly (Jessica Alba).More Idle Hands
- 56Rob Schneider, William Forsythe, Eddie GriffinDeuce Bigalow (Rob Schneider) is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer is hot on his trail.
- #338 of 379 onThe Best Movies Of The '90s, Ranked
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- 57Nicolas Cage, Patricia Arquette, John GoodmanAfter a disheartening and haunting career wears him down, New York City paramedic Frank Pierce (Nicolas Cage) begins to collapse under the strain of saving lives and witnessing deaths. Through the course of a few nights, three co-workers (John Goodman, Ving Rhames, Tom Sizemore) accompany Pierce as he grasps for sanity and pushes to be fired. Before Pierce falls off the edge, he still has a hope when he forms a friendship with a victim's daughter (Patricia Arquette).
- 58Arnold Schwarzenegger, Gabriel Byrne, Kevin PollakWith the millennium approaching, a series of disturbing signs suggests that Satan (Arnold Schwarzenegger) has returned to Earth and is walking the streets of New York City. It seems that Satan needs to find a woman who will bear his child, as the time for the arrival of the anti-Christ draws near.
- 59Jeff Bridges, Tim Robbins, Joan CusackWidowed when his FBI agent wife is killed by an extremist group, college professor Michael Faraday (Jeff Bridges) becomes obsessed with the culture of these groups -- especially when his new all-American neighbors, Oliver (Tim Robbins) and Cheryl Lang (Joan Cusack), start acting suspiciously. With each twist, the mystery deepens and questions loom as to whether Faraday is consumed by fear and driven by paranoia, or whether a lethal conspiracy has been born on Arlington Road.More Arlington Road
- #153 of 252 onThe 200+ Best Psychological Thrillers Of All Time
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- 60Julia Roberts, Hugh Grant, Hugh BonnevilleIn the charming romantic comedy, Notting Hill, William Thacker (Hugh Grant), a humble bookstore owner in London's picturesque Notting Hill district, encounters Anna Scott (Julia Roberts), an American actress and global superstar. Their lives intertwine unexpectedly following a chance meeting in his shop, sparking a whirlwind of events that blend the mundane with the glamorous. As their worlds collide, they navigate the challenges of fame, privacy, and love. Directed by Roger Michell, this film is a delightful exploration of two contrasting lives merging in the most unexpected place.More Notting Hill
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