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The Best Movies of 1999 

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Originally by Ranker Community
Updated August 10, 2019 22.1k votes 1.5k voters 37.3k views 136 items

List Rules Only movies released in theatres 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
Bruce Willis, Mischa Barton, Haley Joel Osment

Released: 1999

Directed by: M. Night Shyamalan

The Sixth Sense is a 1999 American supernatural thriller film written and directed by M. Night Shyamalan. The film tells the story of Cole Sear (Haley Joel Osment), a troubled, isolated boy who ...more

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#5 of 250 The Best Psychological Thrillers of All Time #73 of 1,699 The Most Rewatchable Movieslisted on The Highest Grossing 90s Movies

2
Toy Story 2 is listed (or ranked) 2 on the list The Best Movies of 1999
Tom Hanks, Kelsey Grammer, Tim Allen

Released: 1999

Directed by: John Lasseter, Lee Unkrich, Ash Brannon

Toy Story 2 is a 1999 American computer-animated comedy adventure film produced by Pixar Animation Studios and released by Walt Disney Pictures. Directed by John Lasseter and co-directed by Lee ...more

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3
Fight Club is listed (or ranked) 3 on the list The Best Movies of 1999
Brad Pitt, Jared Leto, Helena Bonham Carter

Released: 1999

Directed by: David Fincher

Fight Club is a 1999 film based on the 1996 novel of the same name by Chuck Palahniuk. The film was directed by David Fincher, and stars Brad Pitt, Edward Norton and Helena Bonham Carter. Norton ...more

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#8 of 250 The Best Psychological Thrillers of All Time #24 of 363 The Best Movies Based On Books 'Fight Club' Fan Theories That Just Might Be True

4
The Green Mile is listed (or ranked) 4 on the list The Best Movies of 1999
Tom Hanks, Gary Sinise, Sam Rockwell

Released: 1999

Directed by: Frank Darabont

The Green Mile is a 1999 American fantasy drama film directed by Frank Darabont and adapted from the 1996 Stephen King novel of the same name. The film is told in a flashback format and stars ...more

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#1 of 292 The Top Tearjerker Movies That Make Men Cry #16 of 1,699 The Most Rewatchable Movies #26 of 599 The Greatest Epic Movies Ever Made

5
American Beauty is listed (or ranked) 5 on the list The Best Movies of 1999
Kevin Spacey, Annette Bening, Mena Suvari

Released: 1999

Directed by: Sam Mendes

American Beauty is a 1999 American drama film directed by Sam Mendes. An advertising executive (Kevin Spacey) has a midlife crisis when he becomes infatuated with his teenage daughter's best ...more

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#292 of 1,699 The Most Rewatchable Movies #233 of 599 The Greatest Epic Movies Ever Madelisted on Every Oscar Winning Film Ever

6
The Matrix is listed (or ranked) 6 on the list The Best Movies of 1999
Keanu Reeves, Hugo Weaving, Carrie-Anne Moss

Released: 1999

Directed by: Andy Wachowski, Lana Wachowski

The Matrix is a 1999 American-Australian science fiction action film written and directed by The Wachowskis, starring Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving, and Joe ...more

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7
10 Things I Hate About Y... is listed (or ranked) 7 on the list The Best Movies of 1999
Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger

Released: 1999

Directed by: Gil Junger

10 Things I Hate About You is a 1999 American teen romantic comedy-drama film. It is directed by Gil Junger and stars Julia Stiles, Heath Ledger and Joseph Gordon-Levitt. The romantic comedy ...more

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#302 of 1,199 The Absolute Funniest Movies Of All Time #6 of 804 The Greatest Chick Flicks Ever Made

8
Office Space is listed (or ranked) 8 on the list The Best Movies of 1999
Jennifer Aniston, John C. McGinley, Mike Judge

Released: 1999

Directed by: Mike Judge

Office Space is a 1999 American comedy film written and directed by Mike Judge. The film satirizes the everyday work life of a typical mid-to-late-1990s software company, it focuses on a handful ...more

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#125 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #127 of 1,699 The Most Rewatchable Movieslisted on The Very Best Movies About Hackers

9
Being John Malkovich is listed (or ranked) 9 on the list The Best Movies of 1999
Cameron Diaz, Brad Pitt, Charlie Sheen

Released: 1999

Directed by: Spike Jonze

Being John Malkovich is a 1999 American fantasy comedy film written by Charlie Kaufman and directed by Spike Jonze. It stars John Cusack, Cameron Diaz and Catherine Keener, with John Malkovich ...more

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#237 of 1,199 The Absolute Funniest Movies Of All Time #117 of 493 The Funniest '90s Movies

10
Austin Powers: The Spy W... is listed (or ranked) 10 on the list The Best Movies of 1999
Elizabeth Hurley, Heather Graham, Will Ferrell

Released: 1999

Directed by: Jay Roach

Austin Powers: The Spy Who Shagged Me is a 1999 action comedy film and the second film in the Austin Powers series. It is preceded by the original film, Austin Powers: International Man of ...more

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11
The Mummy is listed (or ranked) 11 on the list The Best Movies of 1999
Rachel Weisz, Brendan Fraser, Patricia Velásquez

Released: 1999

Directed by: Stephen Sommers

The Mummy is a 1999 American fantasy adventure film written and directed by Stephen Sommers and starring Brendan Fraser, Rachel Weisz, John Hannah, and Kevin J. O'Connor, with Arnold Vosloo in ...more

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#190 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #105 of 1,699 The Most Rewatchable Movieslisted on The Highest Grossing 90s Movies

12
Sleepy Hollow is listed (or ranked) 12 on the list The Best Movies of 1999
Johnny Depp, Christina Ricci, Christopher Walken

Released: 1999

Directed by: Tim Burton

Sleepy Hollow is a 1999 American fantasy horror adventure film directed by Tim Burton. It is a film adaptation loosely inspired by the 1820 short story The Legend of Sleepy Hollow by Washington ...more

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#181 of 1,699 The Most Rewatchable Movies #210 of 599 The Greatest Epic Movies Ever Madelisted on Every Oscar Winning Film Ever

13
Cruel Intentions is listed (or ranked) 13 on the list The Best Movies of 1999
Reese Witherspoon, Sarah Michelle Gellar, Tara Reid

Released: 1999

Directed by: Roger Kumble

Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is an adaptation of Les Liaisons dangereuses, written ...more

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#208 of 804 The Greatest Chick Flicks Ever Made #119 of 624 The Greatest Guilty Pleasure Movies

14
The Iron Giant is listed (or ranked) 14 on the list The Best Movies of 1999
Jennifer Aniston, Vin Diesel, Cloris Leachman

Released: 1999

Directed by: Brad Bird

The Iron Giant is a 1999 American animated science fiction comedy-drama film using both traditional animation and computer animation, produced by Warner Bros. Animation, and based on the 1968 ...more

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#21 of 598 The Best Animated Films Ever #25 of 292 The Top Tearjerker Movies That Make Men Cry

15
Magnolia is listed (or ranked) 15 on the list The Best Movies of 1999
wiabux added Tom Cruise, Julianne Moore, Philip Seymour Hoffman

Released: 1999

Directed by: Paul Thomas Anderson

Magnolia is a 1999 American drama film written, produced, and directed by Paul Thomas Anderson and starring Jeremy Blackman, Tom Cruise, Philip Baker Hall, Philip Seymour Hoffman, Ricky Jay, ...more

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16
Eyes Wide Shut is listed (or ranked) 16 on the list The Best Movies of 1999
Tom Cruise, Nicole Kidman, Stanley Kubrick

Released: 1999

Directed by: Stanley Kubrick

Eyes Wide Shut is a 1999 American thriller film loosely based upon Arthur Schnitzler's 1926 novella Dream Story. The film was directed, produced, and co-written by Stanley Kubrick. It was his ...more

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17
Dogma is listed (or ranked) 17 on the list The Best Movies of 1999
Ben Affleck, Matt Damon, Chris Rock

Released: 1999

Directed by: Kevin Smith

Dogma is a 1999 American comedy film, written and directed by Kevin Smith, who also stars along with Ben Affleck, Matt Damon, Linda Fiorentino, Alan Rickman, Bud Cort, Salma Hayek, Chris Rock, ...more

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#169 of 1,699 The Most Rewatchable Movies #39 of 493 The Funniest '90s Movies

18
American Pie is listed (or ranked) 18 on the list The Best Movies of 1999
Alyson Hannigan, Tara Reid, Shannon Elizabeth

Released: 1999

Directed by: Chris Weitz, Paul Weitz

American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and Chris Weitz, in their directorial film debut. It is the first film in the American Pie theatrical ...more

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19
The Boondock Saints is listed (or ranked) 19 on the list The Best Movies of 1999
Willem Dafoe, Norman Reedus, Billy Connolly

Released: 1999

Directed by: Troy Duffy

The Boondock Saints is a 1999 American film written and directed by Troy Duffy. The film stars Sean Patrick Flanery and Norman Reedus as fraternal twins, Connor and Murphy MacManus, who become ...more

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#162 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #359 of 599 The Greatest Epic Movies Ever Made

20
Galaxy Quest is listed (or ranked) 20 on the list The Best Movies of 1999
Sigourney Weaver, Alan Rickman, Tim Allen

Released: 1999

Directed by: Dean Parisot

Galaxy Quest is a 1999 American science fiction action comedy film directed by Dean Parisot and written by David Howard and Robert Gordon. The film follows the adventures of a troupe of actors ...more

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21
South Park: Bigger, Long... is listed (or ranked) 21 on the list The Best Movies of 1999
George Clooney, Minnie Driver, Isaac Hayes

Released: 1999

Directed by: Trey Parker

South Park: Bigger, Longer & Uncut is a 1999 American adult animated satirical musical comedy film based on the animated television series South Park, and produced, co-written by and ...more

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22
Girl, Interrupted is listed (or ranked) 22 on the list The Best Movies of 1999
Angelina Jolie, Winona Ryder, Whoopi Goldberg

Released: 1999

Directed by: James Mangold

Girl, Interrupted is a 1999 American drama film, and an adaptation of Susanna Kaysen's 1993 memoir of the same name. The film chronicles Kaysen's 18-month stay at a mental institution. Directed ...more

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23
The Talented Mr. Ripley ... is listed (or ranked) 23 on the list The Best Movies of 1999
Gwyneth Paltrow, Cate Blanchett, Matt Damon

Released: 1999

Directed by: Anthony Minghella

The Talented Mr. Ripley is a 1999 American psychological thriller written for the screen and directed by Anthony Minghella. An adaptation of the 1955 Patricia Highsmith novel of the same name, ...more

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24
Election is listed (or ranked) 24 on the list The Best Movies of 1999
Reese Witherspoon, Matthew Broderick, Chris Klein

Released: 1999

Directed by: Alexander Payne

Election is a 1999 American comedy film directed and written by Alexander Payne and adapted by him and Jim Taylor from Tom Perrotta's 1998 novel of the same title. The plot revolves around a ...more

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25
Three Kings is listed (or ranked) 25 on the list The Best Movies of 1999
George Clooney, Mark Wahlberg, Ice Cube

Released: 1999

Directed by: David O. Russell

Three Kings is a 1999 satirical comedy film written and directed by David O. Russell from a story by John Ridley about a men taking gold that takes place during the 1991 Iraqi uprising against ...more

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