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The Best Movies of 1999

Updated September 4, 2020 23.7k votes 1.7k voters 40.7k views124 items

List RulesOnly movies released in theaters in 1999.

A list of the best movies of 1999, from blockbusters like The Matrix to cult classics like The Boondock Saints. The '90s were a decade where Hollywood thrived. In were new stars and big blockbusters and 1999 was no exception. Some the best movies of this year are some of the best teen, coming of age, adventure, comedies and dramas in history. The films on here are very memorable and had audiences on the edges of their seats, and still pack a punch so many years after they were first released. You shouldn't be too surprised by the movies listed on here.

As stated before, some of the best movies of the decade were released in 1999. Who could forget The Sixth Sense with Bruce Willis and Haley Joel Osment, Being John Malkovich with John Cusack, Cameron Diaz and Catherine Keener, and of course, South Park: Bigger, Longer & Uncut. And let's not forget about Girl, Interrupted with Angelina Jolie.

The best movies of 1999 featured some of the biggest stars in the movie business. Whether it was the aforementioned stars continuing their success or the breakout performances featured in American Pie, or established stars like Brad Pitt and Edward Norton in Fight Club.

Some of the best movies of all time were released in 1999. This is the ultimate list of the best movies of 1999, which shouldn't feature the best movies of 1998. Vote and re-rank this list according to how you think the best movies of that year should be reflected. If you notice that there's a movie from this year that should be on this list but is missing, feel free to add it.
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  • The Sixth Sense1
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    The Sixth Sense

    Bruce Willis, Mischa Barton

    Released1999

    Directed byM. Night Shyamalan

    The Sixth Sense is a 1999 American supernatural thriller film written and directed by M. Night...  more
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  • Toy Story 22
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    Toy Story 2

    Tom Hanks, Kelsey Grammer

    Released1999

    Directed byJohn Lasseter, Lee Unkrich, Ash Brannon

    Toy Story 2 is a 1999 American computer-animated comedy adventure film produced by Pixar...  more
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  • 10 Things I Hate About You3
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    125

    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

    10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and...  more
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    #5 of 125 The Greatest Date Movies of All Time#1 of 200 The Best Teen Romance Movies

  • Office Space4
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    Office Space

    Jennifer Aniston, John C. McGinley

    Released1999

    Directed byMike Judge

    Office Space is a 1999 American comedy film written and directed by Mike Judge. The film...  more
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  • The Green Mile5
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    The Green Mile

    Tom Hanks, Gary Sinise

    Released1999

    Directed byFrank Darabont

    The Green Mile is a 1999 American fantasy drama film directed by Frank Darabont and adapted...  more
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  • Fight Club6
    544
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    Fight Club

    Brad Pitt, Jared Leto

    Released1999

    Directed byDavid Fincher

    Fight Club is a 1999 film based on the 1996 novel of the same name by Chuck Palahniuk. The...  more
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  • American Beauty7
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    American Beauty

    Kevin Spacey, Annette Bening

    Released1999

    Directed bySam Mendes

    American Beauty is a 1999 American drama film directed by Sam Mendes. An advertising executive...  more
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  • The Mummy8
    283
    186

    The Mummy

    Rachel Weisz, Brendan Fraser

    Released1999

    Directed byStephen Sommers

    The Mummy is a 1999 American fantasy adventure film written and directed by Stephen Sommers...  more
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  • Cruel Intentions9
    180
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    Cruel Intentions

    Reese Witherspoon, Sarah Michelle Gellar

    Released1999

    Directed byRoger Kumble

    Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe,...  more
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  • The Matrix10
    518
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    The Matrix

    Keanu Reeves, Hugo Weaving

    Released1999

    Directed byAndy Wachowski, Lana Wachowski

    The Matrix is a 1999 American-Australian science fiction action film written and directed by...  more
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  • Sleepy Hollow11
    231
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    Sleepy Hollow

    Johnny Depp, Christina Ricci

    Released1999

    Directed byTim Burton

    Sleepy Hollow is a 1999 American fantasy horror adventure film directed by Tim Burton. It is a...  more
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  • Austin Powers: The Spy Who Shagged Me12
    242
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    Austin Powers: The Spy Who Shagged Me

    Elizabeth Hurley, Heather Graham

    Released1999

    Directed byJay Roach

    Austin Powers: The Spy Who Shagged Me is a 1999 action comedy film and the second film in the...  more
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  • Galaxy Quest13
    186
    120

    Galaxy Quest

    Sigourney Weaver, Alan Rickman

    Released1999

    Directed byDean Parisot

    Galaxy Quest is a 1999 American science fiction action comedy film directed by Dean Parisot...  more
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  • The Boondock Saints14
    168
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    The Boondock Saints

    Willem Dafoe, Norman Reedus

    Released1999

    Directed byTroy Duffy

    The Boondock Saints is a 1999 American film written and directed by Troy Duffy. The film stars...  more
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  • Being John Malkovich15
    223
    182

    Being John Malkovich

    Cameron Diaz, Brad Pitt

    Released1999

    Directed bySpike Jonze

    Being John Malkovich is a 1999 American fantasy comedy film written by Charlie Kaufman and...  more
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  • Girl, Interrupted16
    167
    98

    Girl, Interrupted

    Angelina Jolie, Winona Ryder

    Released1999

    Directed byJames Mangold

    Girl, Interrupted is a 1999 American drama film, and an adaptation of Susanna Kaysen's 1993...  more
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  • The Iron Giant17
    203
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    The Iron Giant

    Jennifer Aniston, Vin Diesel

    Released1999

    Directed byBrad Bird

    The Iron Giant is a 1999 American animated science fiction comedy-drama film using both...  more
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  • South Park: Bigger, Longer & Uncut18
    190
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    South Park: Bigger, Longer & Uncut

    George Clooney, Minnie Driver

    Released1999

    Directed byTrey Parker

    South Park: Bigger, Longer & Uncut is a 1999 American adult animated satirical musical comedy...  more
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  • Election19
    137
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    Election

    Reese Witherspoon, Matthew Broderick

    Released1999

    Directed byAlexander Payne

    Election is a 1999 American comedy film directed and written by Alexander Payne and adapted by...  more
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  • Magnolia20
    198
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    Magnolia

    Tom Cruise, Julianne Moore

    Released1999

    Directed byPaul Thomas Anderson

    Magnolia is a 1999 American drama film written, produced, and directed by Paul Thomas Anderson...  more
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  • Dogma21
    177
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    Dogma

    Ben Affleck, Matt Damon

    Released1999

    Directed byKevin Smith

    Dogma is a 1999 American comedy film written and directed by Kevin Smith. The existence of...  more
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  • Double Jeopardy22
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    Double Jeopardy

    Ashley Judd, Tommy Lee Jones

    Released1999

    Directed byBruce Beresford

    Double Jeopardy is a 1999 American mystery-thriller film directed by Bruce Beresford and...  more
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  • Eyes Wide Shut23
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    Eyes Wide Shut

    Tom Cruise, Nicole Kidman

    Released1999

    Directed byStanley Kubrick

    Eyes Wide Shut is a 1999 American thriller film loosely based upon Arthur Schnitzler's 1926...  more
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  • Three Kings24
    155
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    Three Kings

    George Clooney, Mark Wahlberg

    Released1999

    Directed byDavid O. Russell

    Three Kings is a 1999 satirical comedy film written and directed by David O. Russell from a...  more
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  • Deep Blue Sea25
    119
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    Deep Blue Sea

    Samuel L. Jackson, LL Cool J

    Released1999

    Directed byRenny Harlin

    Deep Blue Sea is a 1999 science fiction horror film, starring Saffron Burrows, Thomas Jane, LL...  more
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