The Best Movies From 1999

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Updated June 23, 2023 32.5K votes 2.1K voters 47.8K views
Over 2.1K Ranker voters have come together to rank this list of The Best Movies From 1999
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
Ranked by
  • The Sixth Sense
    1

    The Sixth Sense

    Bruce Willis, Haley Joel Osment, Toni Collette
    1,077 votes
    • Released: 1999
    • Directed by: M. Night Shyamalan
    In the chilling drama The Sixth Sense, young Cole Sear (Haley Joel Osment) is burdened with an ability to see and interact with the deceased. Struggling to understand his unusual gift, he crosses paths with child psychologist Dr. Malcolm Crowe (Bruce Willis). The doctor, still reeling from a traumatic incident involving a former patient, invests himself in helping Cole cope with his terrifying experiences. This suspenseful thriller, directed by M. Night Shyamalan, was lauded for its unexpected plot twist and earned six Academy Award nominations, solidifying its place as a standout in the supernatural genre.

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  • Fight Club
    2

    Fight Club

    Brad Pitt, Ed Norton, Helena Bonham Carter
    1,343 votes
    • Released: 1999
    • Directed by: David Fincher
    In the gritty urban drama Fight Club, Edward Norton (the unnamed protagonist) finds himself spiraling into the underbelly of his own psyche. Stuck in a monotonous job, he meets Tyler Durden (Brad Pitt), a soap salesman with an unconventional philosophy. Together, they form an underground fight club as a radical form of psychotherapy. As their nocturnal activities escalate, so does their bond. But when Marla Singer (Helena Bonham Carter), a fellow support group crasher, enters their lives, things start to unravel. Directed by David Fincher, Fight Club is a jarring exploration of masculinity and identity that won't soon be forgotten.

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  • The Matrix
    3

    The Matrix

    Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss
    1,353 votes
    • Released: 1999
    • Directed by: Lilly Wachowski, Lana Wachowski
    The Matrix is a groundbreaking science fiction movie that redefined the genre. Thomas Anderson (Keanu Reeves) leads a dual life - a corporate slave by day, and a computer hacker named Neo by night. Contacted by enigmatic Morpheus (Laurence Fishburne), Neo is thrust into a reality-bending journey to uncover the truth about The Matrix, an illusory world created by sentient machines. This dystopian thriller, directed by The Wachowskis, won four Academy Awards for its innovative visual effects and editing techniques. With its complex narrative and philosophical undertones, The Matrix leaves viewers questioning their perception of reality.

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  • The Green Mile
    4

    The Green Mile

    Tom Hanks, David Morse, Michael Clarke Duncan
    987 votes
    • Released: 1999
    • Directed by: Frank Darabont
    In the poignant drama The Green Mile, Paul Edgecomb (Tom Hanks) supervises death row in a 1930s Southern prison. Among the inmates, John Coffey (Michael Clarke Duncan), a gentle giant with mysterious abilities, arrives for a ghastly crime he didn't commit. As Paul delves into John's enigmatic character, he discovers an extraordinary secret that challenges his beliefs. Adapted from Stephen King's novel, this film uniquely intertwines fantasy and period drama elements. Garnering four Academy Award nominations, it remains a compelling exploration of justice and humanity.

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  • Office Space
    5

    Office Space

    Ron Livingston, Jennifer Aniston, David Herman
    820 votes
    • Released: 1999
    • Directed by: Mike Judge
    In the comedy film Office Space, Peter Gibbons (Ron Livingston) is a disgruntled software engineer stuck in a soul-sucking job at Initech Corporation. Alongside his equally tormented coworkers, Samir Nagheenanajar (Ajay Naidu) and Michael Bolton (David Herman), they suffer under the oppressive management of Bill Lumbergh (Gary Cole). The trio hatch a plan to steal fractions of pennies from the company, a scheme that spirals out of control. Directed by Mike Judge, this 1999 cult classic provides a satirical look at corporate culture and office politics.

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  • The Mummy
    6

    The Mummy

    Brendan Fraser, Rachel Weisz, John Hannah
    772 votes
    • Released: 1999
    • Directed by: Stephen Sommers
    In the heart-pounding adventure film The Mummy, Nick Morton (Tom Cruise) stumbles upon an ancient tomb in the midst of a battle-ridden Middle East. Unbeknownst to him, the tomb houses the malevolent Princess Ahmanet (Sofia Boutella), cursed for eternity by her own people. As the princess awakens from her crypt, she embarks on a vengeful mission to reclaim what is rightfully hers. The movie, rich in Egyptian mythology and action-packed sequences, unravels as Morton battles this resurrected ancient power. This captivating tale masterfully intertwines history and fantasy, leaving audiences on the edge of their seats.

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