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The Best Movies of 1999

Updated September 4, 2020 22.5k votes 1.6k voters 39.6k 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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  • 1
    The Sixth Sense is listed (or ranked) 1 on the list The Best Movies of 1999
    424
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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 on Wikipediaamazon buy button
  • 2
    Toy Story 2 is listed (or ranked) 2 on the list The Best Movies of 1999
    354
    183

    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 on Wikipediaamazon buy button

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  • 3
    10 Things I Hate About You is listed (or ranked) 3 on the list The Best Movies of 1999
    267
    119

    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 on Wikipediaamazon buy button
  • 4
    Office Space is listed (or ranked) 4 on the list The Best Movies of 1999
    296
    151

    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 on Wikipediaamazon buy button
  • 5
    Fight Club is listed (or ranked) 5 on the list The Best Movies of 1999
    548
    392

    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 on Wikipediaamazon buy button

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  • 6
    The Green Mile is listed (or ranked) 6 on the list The Best Movies of 1999
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    261

    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 on Wikipediaamazon buy button

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  • 7
    American Beauty is listed (or ranked) 7 on the list The Best Movies of 1999
    350
    244

    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 on Wikipediaamazon buy button
  • 8
    Cruel Intentions is listed (or ranked) 8 on the list The Best Movies of 1999
    177
    93

    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 on Wikipediaamazon buy button
  • 9
    The Matrix is listed (or ranked) 9 on the list The Best Movies of 1999
    507
    422

    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 on Wikipediaamazon buy button

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  • 10
    The Mummy is listed (or ranked) 10 on the list The Best Movies of 1999
    277
    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 on Wikipediaamazon buy button

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  • 11
    Sleepy Hollow is listed (or ranked) 11 on the list The Best Movies of 1999
    229
    166

    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 on Wikipediaamazon buy button
  • 12
    Austin Powers: The Spy Who Sha is listed (or ranked) 12 on the list The Best Movies of 1999
    241
    177

    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 on Wikipediaamazon buy button
  • 13
    Being John Malkovich is listed (or ranked) 13 on the list The Best Movies of 1999
    223
    184

    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 on Wikipediaamazon buy button
  • 14
    The Boondock Saints is listed (or ranked) 14 on the list The Best Movies of 1999
    165
    116

    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 on Wikipediaamazon buy button

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  • 15
    Galaxy Quest is listed (or ranked) 15 on the list The Best Movies of 1999
    181
    121

    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 on Wikipediaamazon buy button
  • 16
    Girl, Interrupted is listed (or ranked) 16 on the list The Best Movies of 1999
    163
    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 on Wikipediaamazon buy button

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  • 17
    Magnolia is listed (or ranked) 17 on the list The Best Movies of 1999
    204
    173

    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 on Wikipediaamazon buy button

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  • 18
    Election is listed (or ranked) 18 on the list The Best Movies of 1999
    136
    96

    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 on Wikipediaamazon buy button

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  • 19
    South Park: Bigger, Longer & U is listed (or ranked) 19 on the list The Best Movies of 1999
    191
    120

    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 on Wikipediaamazon buy button
  • 20
    Eyes Wide Shut is listed (or ranked) 20 on the list The Best Movies of 1999
    207
    177

    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 on Wikipediaamazon buy button
  • 21
    The Iron Giant is listed (or ranked) 21 on the list The Best Movies of 1999
    201
    173

    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 on Wikipediaamazon buy button

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  • 22
    Dogma is listed (or ranked) 22 on the list The Best Movies of 1999
    176
    153

    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 on Wikipediaamazon buy button
  • 23
    Deep Blue Sea is listed (or ranked) 23 on the list The Best Movies of 1999
    119
    79

    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 on Wikipediaamazon buy button

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  • 24
    The Blair Witch Project is listed (or ranked) 24 on the list The Best Movies of 1999
    165
    134

    The Blair Witch Project

    Heather Donahue, Joshua Leonard

    Released1999

    Directed byDaniel Myrick, Eduardo Sánchez

    The Blair Witch Project is a 1999 American found footage horror film written, directed and... more on Wikipediaamazon buy button

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  • 25
    Three Kings is listed (or ranked) 25 on the list The Best Movies of 1999
    154
    134

    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 on Wikipediaamazon buy button

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