90s Movies 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
373 194
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
2
389 187
Fight Club is listed (or ranked) 2 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
3
312 144
The Sixth Sense is listed (or ranked) 3 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
4
272 129
Toy Story 2 is listed (or ranked) 4 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
5
289 167
The Green Mile is listed (or ranked) 5 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
6
281 161
American Beauty is listed (or ranked) 6 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 and written by Alan Ball. Kevin Spacey stars as Lester Burnham, an office worker who has a midlife crisis when he becomes ...more
7
187 134
Being John Malkovich is listed (or ranked) 7 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
8
219 124
Office Space is listed (or ranked) 8 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
9
151 139
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
10
164 132
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
11
210 146
The Mummy is listed (or ranked) 11 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
12
186 138
Austin Powers: The Spy Who Sha... is listed (or ranked) 12 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
13
215 156
American Pie is listed (or ranked) 13 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
14
167 149
Sleepy Hollow is listed (or ranked) 14 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
15
136 138
The Talented Mr. Ripley is listed (or ranked) 15 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
16
190 97
10 Things I Hate About You is listed (or ranked) 16 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
17
154 140
Eyes Wide Shut is listed (or ranked) 17 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
18
146 137
Dogma is listed (or ranked) 18 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
19
119 109
Three Kings is listed (or ranked) 19 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
20
139 112
South Park: Bigger, Longer & U... is listed (or ranked) 20 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
21
139 100
Galaxy Quest is listed (or ranked) 21 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
22
100 87
The Insider is listed (or ranked) 22 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
23
113 139
Notting Hill is listed (or ranked) 23 on the list The Best Movies of 1999
Julia Roberts, Alec Baldwin, Mischa Barton
Notting Hill is a 1999 British romantic comedy film set in Notting Hill, London, released on 21 May 1999. The screenplay was by Richard Curtis and the film was produced by Duncan Kenworthy and ...more
24
129 142
Big Daddy is listed (or ranked) 24 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
25
119 99
The Boondock Saints is listed (or ranked) 25 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