Entertainment

The Best Movies of 1999  

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Originally by Ranker Community
20.1k votes 1.3k voters 34.2k views 138 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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26
Cruel Intentions is listed (or ranked) 26 on the list The Best Movies of 1999
Reese Witherspoon, Sarah Michelle Gellar, Tara Reid
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
27
Any Given Sunday is listed (or ranked) 27 on the list The Best Movies of 1999
Cameron Diaz, Al Pacino, Jamie Foxx
Any Given Sunday is a 1999 American drama film directed by Oliver Stone depicting a fictional professional American football team. The film features an ensemble cast, consisting of Al Pacino, ...more
28
Go is listed (or ranked) 28 on the list The Best Movies of 1999
Katie Holmes, Melissa McCarthy, Timothy Olyphant
Go is a 1999 comedy film written by John August and directed by Doug Liman, with three intertwining plots that happen to involve one deal. The film stars William Fichtner, Katie Holmes, Jay ...more
29
Election is listed (or ranked) 29 on the list The Best Movies of 1999
Reese Witherspoon, Matthew Broderick, Chris Klein
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
30
Girl, Interrupted is listed (or ranked) 30 on the list The Best Movies of 1999
Angelina Jolie, Winona Ryder, Whoopi Goldberg
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
31
Varsity Blues is listed (or ranked) 31 on the list The Best Movies of 1999
Ali Larter, Paul Walker, Amy Smart
Varsity Blues is a 1999 American coming-of-age sports comedy-drama film directed by Brian Robbins that follows a small-town high school football team and their overbearing coach through a ...more
32
Boys Don't Cry is listed (or ranked) 32 on the list The Best Movies of 1999
Boys Don't Cry Hilary Swank, Chloë Sevigny, Natalie Zea
Boys Don't Cry is a 1999 American independent romantic drama film directed by Kimberly Peirce and co-written by Andy Bienen. The film is a dramatization of the real-life story of Brandon Teena, ...more
33
The Blair Witch Project is listed (or ranked) 33 on the list The Best Movies of 1999
Heather Donahue, Joshua Leonard, Michael C. Williams
The Blair Witch Project is a 1999 American found footage horror film written, directed and edited by Daniel Myrick and Eduardo Sánchez. The film was produced by the Haxan Films production ...more
34
Man on the Moon is listed (or ranked) 34 on the list The Best Movies of 1999
Courtney Love, Jim Carrey, Danny DeVito
Man on the Moon is a 1999 American biographical comedy–drama film about the late American entertainer Andy Kaufman, starring Jim Carrey. The film was directed by Miloš Forman and also features ...more
35
The Hurricane is listed (or ranked) 35 on the list The Best Movies of 1999
Denzel Washington, Liev Schreiber, Rod Steiger
The Hurricane is a 1999 biographical film directed by Norman Jewison, and starring Denzel Washington. The script was adapted by Armyan Bernstein and Dan Gordon from the books Lazarus and the ...more
36
Analyze This is listed (or ranked) 36 on the list The Best Movies of 1999
Robert De Niro, Billy Crystal, Lisa Kudrow
Analyze This is a 1999 comedy film directed by Harold Ramis, who co-wrote the screenplay with playwright Kenneth Lonergan and Peter Tolan. The film stars Robert De Niro as a mafioso and Billy ...more
37
Arlington Road is listed (or ranked) 37 on the list The Best Movies of 1999
Jeff Bridges, Tim Robbins, Joan Cusack
Arlington Road is a 1999 American mystery thriller film, which tells the story of a widowed George Washington University professor who suspects his new neighbors are involved in terrorism and ...more
38
Notting Hill is listed (or ranked) 38 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
39
Tarzan is listed (or ranked) 39 on the list The Best Movies of 1999
Rosie O'Donnell, Glenn Close, Minnie Driver
Tarzan is a 1999 American animated adventure musical film produced by Walt Disney Feature Animation and released by Walt Disney Pictures. The 37th film in the Walt Disney Animated Classics, it ...more
40
Stir of Echoes is listed (or ranked) 40 on the list The Best Movies of 1999
Jennifer Morrison, Kevin Bacon, Illeana Douglas
Stir of Echoes is a supernatural horror-thriller released in the US in 1999, starring Kevin Bacon and directed by David Koepp. The film is loosely based on the novel A Stir of Echoes by Richard ...more
41
The Straight Story is listed (or ranked) 41 on the list The Best Movies of 1999
weik added Sissy Spacek, Harry Dean Stanton, Richard Farnsworth
The Straight Story is a 1999 biographical drama film directed by David Lynch. The film was edited and produced by Mary Sweeney, Lynch's longtime partner and co-worker. She co-wrote the script ...more
42
The World Is Not Enough is listed (or ranked) 42 on the list The Best Movies of 1999
Pierce Brosnan, Denise Richards, John Cleese
The World Is Not Enough is the nineteenth spy film in the James Bond series, and the third to star Pierce Brosnan as the fictional MI6 agent James Bond. The film was directed by Michael Apted, ...more
43
Deep Blue Sea is listed (or ranked) 43 on the list The Best Movies of 1999
looksharp added Samuel L. Jackson, LL Cool J, Thomas Jane
Deep Blue Sea is a 1999 science fiction horror film, starring Saffron Burrows, Thomas Jane, LL Cool J, Michael Rapaport, Stellan Skarsgård and Samuel L. Jackson. The film was directed by ...more
44
October Sky is listed (or ranked) 44 on the list The Best Movies of 1999
Jake Gyllenhaal, Laura Dern, Chris Cooper
October Sky is a 1999 American biographical film directed by Joe Johnston, starring Jake Gyllenhaal, Chris Cooper and Laura Dern. It is based on the true story of Homer Hickam, a coal miner's ...more
45
Double Jeopardy is listed (or ranked) 45 on the list The Best Movies of 1999
Ashley Judd, Tommy Lee Jones, Bruce Campbell
Double Jeopardy is a 1999 American mystery-thriller film directed by Bruce Beresford and starring Tommy Lee Jones, Ashley Judd, and Bruce Greenwood. The film is about a woman who is framed.
46
The Thomas Crown Affair is listed (or ranked) 46 on the list The Best Movies of 1999
Pierce Brosnan, Faye Dunaway, Rene Russo
The Thomas Crown Affair is a 1999 American film directed by John McTiernan. The film, starring Pierce Brosnan, Rene Russo and Denis Leary, is a remake of the 1968 film of the same name. The film ...more
47
The Virgin Suicides is listed (or ranked) 47 on the list The Best Movies of 1999
Kirsten Dunst, Kathleen Turner, Danny DeVito
The film is a 1999 American drama written and directed by Sofia Coppola, produced by her father Francis Ford Coppola, starring James Woods, Kathleen Turner, Kirsten Dunst, Josh Hartnett, and A. ...more
48
Payback is listed (or ranked) 48 on the list The Best Movies of 1999
Mel Gibson, Lucy Liu, Maria Bello
Payback is a 1999 American action film directed by Brian Helgeland and starring Mel Gibson, Gregg Henry, Maria Bello and David Paymer. It was based on the novel The Hunter by Donald E. Westlake ...more
49
The Bone Collector is listed (or ranked) 49 on the list The Best Movies of 1999
wiabux added Angelina Jolie, Denzel Washington, Queen Latifah
The Bone Collector is a 1999 psychological thriller film starring Denzel Washington and Angelina Jolie, directed by Phillip Noyce and produced by Martin Bregman. The movie was based on the novel ...more
50
Blast from the Past is listed (or ranked) 50 on the list The Best Movies of 1999
looksharp added Alicia Silverstone, Christopher Walken, Brendan Fraser
Blast from the Past is a 1999 American romantic comedy film based on a story and directed by Hugh Wilson, and starring Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek and ...more