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The 25 best movies of 1999

by Slampage • Created 14 years ago • Modified 14 years ago
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  • 25 titles
  • Brad Pitt and Edward Norton in Fight Club (1999)

    1. Fight Club

    19992h 19mR67Metascore
    8.8 (2.5M)
    An insomniac office worker and a devil-may-care soap maker form an underground fight club that evolves into much more.
    DirectorDavid FincherStarsBrad PittEdward NortonMeat Loaf
  • Keanu Reeves, Laurence Fishburne, Joe Pantoliano, and Carrie-Anne Moss in The Matrix (1999)

    2. The Matrix

    19992h 16mR73Metascore
    8.7 (2.2M)
    When a beautiful stranger leads computer hacker Neo to a forbidding underworld, he discovers the shocking truth--the life he knows is the elaborate deception of an evil cyber-intelligence.
    DirectorsLana WachowskiLilly WachowskiStarsKeanu ReevesLaurence FishburneCarrie-Anne Moss
  • Movie Poster

    3. The Green Mile

    19993h 9mR61Metascore
    8.6 (1.5M)
    A death row guard learns that a gentle giant in his charge possesses a mysterious gift.
    DirectorFrank DarabontStarsTom HanksMichael Clarke DuncanDavid Morse
  • Tom Hanks and Tim Allen in Toy Story 2 (1999)

    4. Toy Story 2

    19991h 32mG88Metascore
    7.9 (645K)
    When Woody is stolen by a toy collector, Buzz and his friends set out on a rescue mission to save Woody before he becomes a museum toy property with his roundup gang Jessie, Prospector, and Bullseye.
    DirectorsJohn LasseterAsh BrannonLee UnkrichStarsTom HanksTim AllenJoan Cusack
  • Kevin Spacey, Thora Birch, Mena Suvari, and Wes Bentley in American Beauty (1999)

    5. American Beauty

    19992h 2mR84Metascore
    8.3 (1.2M)
    A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend.
    DirectorSam MendesStarsKevin SpaceyAnnette BeningThora Birch
  • Eric Idle, Matt Stone, Isaac Hayes, Trey Parker, Mary Kay Bergman, Franchesca Clifford, Anthony Cross-Thomas, and Jesse Brant Howell in South Park: Bigger, Longer & Uncut (1999)

    6. South Park: Bigger, Longer & Uncut

    19991h 21mR73Metascore
    7.7 (220K)
    When Eric Cartman and his friends go see an R-rated movie, they start cursing and their parents think that Canada is to blame.
    DirectorTrey ParkerStarsTrey ParkerMatt StoneMary Kay Bergman
  • Christopher Walken in Sleepy Hollow (1999)

    7. Sleepy Hollow

    19991h 45mR65Metascore
    7.3 (400K)
    Ichabod Crane is sent to Sleepy Hollow to investigate the decapitations of three people; the culprit is legendary apparition The Headless Horseman.
    DirectorTim BurtonStarsJohnny DeppChristina RicciMiranda Richardson
  • Version A, 1 sheet

    8. Office Space

    19991h 29mR68Metascore
    7.6 (299K)
    Three company workers who hate their jobs decide to rebel against their greedy boss.
    DirectorMike JudgeStarsRon LivingstonJennifer AnistonDavid Herman
  • Salma Hayek, Ben Affleck, Matt Damon, Linda Fiorentino, Alan Rickman, Chris Rock, Kevin Smith, and Jason Mewes in Dogma (1999)

    9. Dogma

    19992h 10mR62Metascore
    7.3 (234K)
    An abortion clinic worker with a special heritage is called upon to save the existence of humanity from being negated by two renegade angels trying to exploit a loop-hole and reenter Heaven.
    DirectorKevin SmithStarsBen AffleckMatt DamonLinda Fiorentino
  • Denzel Washington in The Hurricane (1999)

    10. The Hurricane

    19992h 26mR74Metascore
    7.6 (105K)
    The story of Rubin 'Hurricane' Carter, a boxer wrongly imprisoned for murder, and the people who aided in his fight to prove his innocence.
    DirectorNorman JewisonStarsDenzel WashingtonVicellous ShannonDeborah Kara Unger
  • Cameron Diaz, Al Pacino, James Woods, Dennis Quaid, Jamie Foxx, and LL Cool J in Any Given Sunday (1999)

    11. Any Given Sunday

    19992h 42mR52Metascore
    6.9 (129K)
    A behind-the-scenes look at the life-and-death struggles of modern-day gladiators and those who lead them.
    DirectorOliver StoneStarsAl PacinoDennis QuaidCameron Diaz
  • Winona Ryder in Girl, Interrupted (1999)

    12. Girl, Interrupted

    19992h 7mR51Metascore
    7.3 (224K)
    Directionless teenager Susanna is rushed to Claymoore, a mental institution, after a supposed suicide attempt. There she befriends a group of troubled women who deeply influence her life.
    DirectorJames MangoldStarsWinona RyderAngelina JolieClea DuVall
  • Haley Joel Osment in The Sixth Sense (1999)

    13. The Sixth Sense

    19991h 47mPG-1364Metascore
    8.2 (1.1M)
    After being shot by a resentful former patient whom he failed to help, a Philadelphia child psychologist seeks redemption by treating a young boy with a disturbing secret.
    DirectorM. Night ShyamalanStarsBruce WillisHaley Joel OsmentToni Collette
  • Jude Law, Matt Damon, and Gwyneth Paltrow in The Talented Mr. Ripley (1999)

    14. The Talented Mr. Ripley

    19992h 19mR76Metascore
    7.4 (261K)
    In late 1950s New York, a young underachiever named Tom Ripley is sent to Italy to retrieve Dickie Greenleaf, a rich and spoiled millionaire playboy. But when the errand fails, Ripley takes extreme measures.
    DirectorAnthony MinghellaStarsMatt DamonGwyneth PaltrowJude Law
  • Russell Crowe and Al Pacino in The Insider (1999)

    15. The Insider

    19992h 37mR85Metascore
    7.8 (186K)
    A research chemist comes under personal and professional attack when he decides to appear in a 60 Minutes exposé on Big Tobacco.
    DirectorMichael MannStarsRussell CroweAl PacinoChristopher Plummer
  • Mike Myers and Heather Graham in Austin Powers: The Spy Who Shagged Me (1999)

    16. Austin Powers: The Spy Who Shagged Me

    19991h 35mPG-1359Metascore
    6.7 (256K)
    Dr. Evil is back and has invented a new time machine that allows him to go back to the 1960s and steal Austin Powers' mojo, inadvertently leaving him "shagless".
    DirectorJay RoachStarsMike MyersHeather GrahamMichael York
  • Hilary Swank in Boys Don't Cry (1999)

    17. Boys Don't Cry

    19991h 58mR86Metascore
    7.5 (106K)
    A young transgender man named Brandon navigates love, life, and trying to pass as a boy in rural Nebraska.
    DirectorKimberly PeirceStarsHilary SwankChloë SevignyPeter Sarsgaard
  • Julia Roberts and Hugh Grant in Notting Hill (1999)

    18. Notting Hill

    19992h 4mPG-1368Metascore
    7.2 (365K)
    A set of circumstances makes Anna Scott, a famous actress, fall in love with William Thacker, owner of a bookstore in Notting Hill. But the paparazzi's fascination with her complicates their bond.
    DirectorRoger MichellStarsHugh GrantJulia RobertsRichard McCabe
  • Robert De Niro and Billy Crystal in Analyze This (1999)

    19. Analyze This

    19991h 43mR60Metascore
    6.7 (165K)
    A comedy about a psychiatrist whose number-one patient is an insecure mob boss.
    DirectorHarold RamisStarsRobert De NiroBilly CrystalLisa Kudrow
  • Mena Suvari, Jason Biggs, Alyson Hannigan, Chris Klein, Natasha Lyonne, Thomas Ian Nicholas, Tara Reid, Seann William Scott, and Eddie Kaye Thomas in American Pie (1999)

    20. American Pie

    19991h 35mR58Metascore
    7.0 (452K)
    Four teenage boys enter a pact to lose their virginity by prom night.
    DirectorPaul WeitzStarsJason BiggsChris KleinThomas Ian Nicholas
  • All About My Mother (1999)

    21. All About My Mother

    19991h 41mR87Metascore
    7.8 (107K)
    A comedy-drama about a bereaved mother, an overwrought actress, her jealous lover, and a pregnant nun.
    DirectorPedro AlmodóvarStarsCecilia RothMarisa ParedesCandela Peña
  • The Lord's Lantern in Budapest (1998)

    22. The Lord's Lantern in Budapest

    19981h 43m
    6.7 (1.1K)
    A portrait of the wild capitalism after the regime change in Hungary, in which the characters show with a continuous change of identity how interests override everything. But in the end, everyone ends up in the same place and the same way.
    DirectorMiklós JancsóStarsZoltán MucsiPéter SchererJózsef Szarvas
  • John Cusack, Cameron Diaz, and Catherine Keener in Being John Malkovich (1999)

    23. Being John Malkovich

    19991h 53mR90Metascore
    7.7 (362K)
    A puppeteer discovers a portal that leads literally into the head of movie star John Malkovich.
    DirectorSpike JonzeStarsJohn CusackCameron DiazCatherine Keener
  • George Clooney, Mark Wahlberg, and Ice Cube in Three Kings (1999)

    24. Three Kings

    19991h 54mR82Metascore
    7.1 (184K)
    In the aftermath of the Persian Gulf War, four soldiers set out to steal gold that was stolen from Kuwait, but they discover people who desperately need their help.
    DirectorDavid O. RussellStarsGeorge ClooneyMark WahlbergIce Cube
  • Nicolas Cage in Bringing Out the Dead (1999)

    25. Bringing Out the Dead

    19992h 1mR72Metascore
    6.9 (79K)
    Haunted by the patients he failed to save, a monumentally burned-out Manhattan ambulance paramedic fights to maintain his sanity over three increasingly turbulent nights.
    DirectorMartin ScorseseStarsNicolas CagePatricia ArquetteJohn Goodman

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