Entertainment

The Best Movies of 1999 

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Originally by Ranker Community
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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.
list ordered by
1
The Matrix is listed (or ranked) 1 on the list The Best Movies of 1999
Keanu Reeves, Hugo Weaving, Carrie-Anne Moss
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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2
Toy Story 2 is listed (or ranked) 2 on the list The Best Movies of 1999
Tom Hanks, Kelsey Grammer, Tim Allen
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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#249 of 1,699 The Most Rewatchable Moviesfeaturing The Best Toy Story Characters in the Whole Series, Rankedlisted on The Highest Grossing 90s Movies

3
Fight Club is listed (or ranked) 3 on the list The Best Movies of 1999
Brad Pitt, Jared Leto, Helena Bonham Carter
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 254 The Best Psychological Thrillers of All Time #24 of 348 The Best Movies Based On Booksfeaturing 20 Surprising Facts You Didn't Know About Fight Club

4
The Sixth Sense is listed (or ranked) 4 on the list The Best Movies of 1999
Bruce Willis, Mischa Barton, Haley Joel Osment
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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#3 of 254 The Best Psychological Thrillers of All Time #84 of 1,699 The Most Rewatchable Movieslisted on The Highest Grossing 90s Movies

5
American Beauty is listed (or ranked) 5 on the list The Best Movies of 1999
Kevin Spacey, Annette Bening, Mena Suvari
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 Green Mile is listed (or ranked) 6 on the list The Best Movies of 1999
Tom Hanks, Gary Sinise, Sam Rockwell
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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#48 of 1,699 The Most Rewatchable Movies #15 of 157 The Best Movies You Never Want to Watch Again #12 of 348 The Best Movies Based On Books

7
Office Space is listed (or ranked) 7 on the list The Best Movies of 1999
Jennifer Aniston, John C. McGinley, 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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#82 of 1,699 The Most Rewatchable Movies #5 of 1,007 The All-Time Greatest Comedy Filmslisted on The Very Best Movies About Hackers

8
Being John Malkovich is listed (or ranked) 8 on the list The Best Movies of 1999
Cameron Diaz, Brad Pitt, Charlie Sheen
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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9
The Iron Giant is listed (or ranked) 9 on the list The Best Movies of 1999
Jennifer Aniston, Vin Diesel, Cloris Leachman
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 589 The Best Animated Films Ever #237 of 348 The Best Movies Based On Books

10
Magnolia is listed (or ranked) 10 on the list The Best Movies of 1999
wiabux added
Tom Cruise, Julianne Moore, Philip Seymour Hoffman
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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#561 of 599 The Greatest Epic Movies Ever Made #172 of 324 Movies with the Best Soundtracks #381 of 460 The Most Quotable Movies of All Time

11
Austin Powers: The Spy W... is listed (or ranked) 11 on the list The Best Movies of 1999
Elizabeth Hurley, Heather Graham, Will Ferrell
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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12
The Mummy is listed (or ranked) 12 on the list The Best Movies of 1999
Rachel Weisz, Brendan Fraser, Patricia Velásquez
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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#104 of 1,699 The Most Rewatchable Movies #4 of 97 The Greatest Movie Remakes of All Timelisted on The Highest Grossing 90s Movies

13
Eyes Wide Shut is listed (or ranked) 13 on the list The Best Movies of 1999
Tom Cruise, Nicole Kidman, 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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#74 of 157 The Best Movies You Never Want to Watch Again #12 of 156 The Most Confusing Movies Ever Made

14
The Talented Mr. Ripley ... is listed (or ranked) 14 on the list The Best Movies of 1999
Gwyneth Paltrow, Cate Blanchett, Matt Damon
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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#434 of 803 The Greatest Chick Flicks Ever Made #155 of 710 The Best Movies Roger Ebert Gave Four Stars #67 of 90 List of Movies Like Inception

15
10 Things I Hate About Y... is listed (or ranked) 15 on the list The Best Movies of 1999
Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger
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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#6 of 803 The Greatest Chick Flicks Ever Made #301 of 1,198 The Absolute Funniest Movies Of All Time

16
Three Kings is listed (or ranked) 16 on the list The Best Movies of 1999
George Clooney, Mark Wahlberg, Ice Cube
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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17
Sleepy Hollow is listed (or ranked) 17 on the list The Best Movies of 1999
Johnny Depp, Christina Ricci, Christopher Walken
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 #206 of 599 The Greatest Epic Movies Ever Madelisted on Every Oscar Winning Film Ever

18
American Pie is listed (or ranked) 18 on the list The Best Movies of 1999
Alyson Hannigan, Tara Reid, Shannon Elizabeth
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
Dogma is listed (or ranked) 19 on the list The Best Movies of 1999
Ben Affleck, Matt Damon, Chris Rock
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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#167 of 1,699 The Most Rewatchable Movies #143 of 460 The Most Quotable Movies of All Time

20
The Insider is listed (or ranked) 20 on the list The Best Movies of 1999
Al Pacino, Russell Crowe, Christopher Plummer
The Insider is a 1999 American drama film directed by Michael Mann, based on the true story of a 60 Minutes segment about Jeffrey Wigand, a whistleblower in the tobacco industry. The 60 Minutes ...more
21
The Boondock Saints is listed (or ranked) 21 on the list The Best Movies of 1999
Willem Dafoe, Norman Reedus, Billy Connolly
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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22
Galaxy Quest is listed (or ranked) 22 on the list The Best Movies of 1999
Sigourney Weaver, Alan Rickman, Tim Allen
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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23
South Park: Bigger, Long... is listed (or ranked) 23 on the list The Best Movies of 1999
George Clooney, Minnie Driver, Isaac Hayes
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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24
Star Wars Episode I: The... is listed (or ranked) 24 on the list The Best Movies of 1999
Natalie Portman, Keira Knightley, Ewan McGregor
(32 Years Before Episode IV) Stranded on the desert planet Tatooine after rescuing young Queen Amidala from the impending invasion of Naboo, Jedi apprentice Obi-Wan Kenobi and his Jedi Master ...more

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25
Big Daddy is listed (or ranked) 25 on the list The Best Movies of 1999
Adam Sandler, Jon Stewart, Steve Buscemi
Big Daddy is a 1999 American comedy film directed by Dennis Dugan and starring Adam Sandler. The film was produced by Robert Simonds and released on June 25, 1999, by Columbia Pictures where it ...more

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