90s Movies The Best Movies of 1999  

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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.

1
252 121
The Matrix is listed (or ranked) 1 on the list The Best Movies of 1999
The Matrix 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
263 127
Fight Club is listed (or ranked) 2 on the list The Best Movies of 1999
Fight Club 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
218 84
The Sixth Sense is listed (or ranked) 3 on the list The Best Movies of 1999
The Sixth Sense 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, a troubled, isolated boy who is able to see and ...more

4
210 105
The Green Mile is listed (or ranked) 4 on the list The Best Movies of 1999
The Green Mile 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

5
193 100
American Beauty is listed (or ranked) 5 on the list The Best Movies of 1999
American Beauty 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

6
185 85
Toy Story 2 is listed (or ranked) 6 on the list The Best Movies of 1999
Toy Story 2 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

7
115 91
Being John Malkovich is listed (or ranked) 7 on the list The Best Movies of 1999
Being John Malkovich 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
135 87
Office Space is listed (or ranked) 8 on the list The Best Movies of 1999
Office Space 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
102 89
The Iron Giant is listed (or ranked) 9 on the list The Best Movies of 1999
The Iron Giant 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
141 88
The Mummy is listed (or ranked) 10 on the list The Best Movies of 1999
The Mummy 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

11
109 103
Sleepy Hollow is listed (or ranked) 11 on the list The Best Movies of 1999
Sleepy Hollow 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

12
96 87
Magnolia is listed (or ranked) 12 on the list The Best Movies of 1999
wiabux added Magnolia 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

13
91 101
The Talented Mr. Ripley is listed (or ranked) 13 on the list The Best Movies of 1999
The Talented Mr. Ripley 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

14
123 94
Austin Powers: The Spy Who Sha... is listed (or ranked) 14 on the list The Best Movies of 1999
Austin Powers: The Spy Who Shagged Me 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

15
142 114
American Pie is listed (or ranked) 15 on the list The Best Movies of 1999
American Pie Alyson Hannigan, Tara Reid, Shannon Elizabeth American Pie is a 1999 teen sex 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 ...more

16
101 97
Eyes Wide Shut is listed (or ranked) 16 on the list The Best Movies of 1999
Eyes Wide Shut Tom Cruise, Nicole Kidman, Stanley Kubrick Eyes Wide Shut is a 1999 American erotic 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 ...more

17
115 66
10 Things I Hate About You is listed (or ranked) 17 on the list The Best Movies of 1999
10 Things I Hate About You 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

18
103 96
Dogma is listed (or ranked) 18 on the list The Best Movies of 1999
Dogma 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
71 72
Three Kings is listed (or ranked) 19 on the list The Best Movies of 1999
Three Kings George Clooney, Mark Wahlberg, Ice Cube Three Kings is a 1999 satirical war-comedy film written and directed by David O. Russell from a story by John Ridley about a gold heist that takes place during the 1991 Iraqi uprising against ...more

20
96 128
Star Wars Episode I: The Phant... is listed (or ranked) 20 on the list The Best Movies of 1999
Star Wars Episode I: The Phantom Menace 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

21
92 81
South Park: Bigger, Longer & U... is listed (or ranked) 21 on the list The Best Movies of 1999
South Park: Bigger, Longer & Uncut 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

22
74 92
Notting Hill is listed (or ranked) 22 on the list The Best Movies of 1999
Notting Hill 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, who had written Four Weddings and a Funeral, and ...more

23
89 98
Big Daddy is listed (or ranked) 23 on the list The Best Movies of 1999
Big Daddy 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

24
59 62
The Insider is listed (or ranked) 24 on the list The Best Movies of 1999
The Insider 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

25
83 64
Galaxy Quest is listed (or ranked) 25 on the list The Best Movies of 1999
Galaxy Quest 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

26
76 65
The Boondock Saints is listed (or ranked) 26 on the list The Best Movies of 1999
The Boondock Saints Willem Dafoe, Norman Reedus, Billy Connolly The Boondock Saints is a 1999 American crime film written and directed by Troy Duffy. The film stars Sean Patrick Flanery and Norman Reedus as fraternal twins, Connor and Murphy MacManus, who ...more

27
58 83
The World Is Not Enough is listed (or ranked) 27 on the list The Best Movies of 1999
The World Is Not Enough 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

28
55 62
Any Given Sunday is listed (or ranked) 28 on the list The Best Movies of 1999
Any Given Sunday 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

29
52 66
Stir of Echoes is listed (or ranked) 29 on the list The Best Movies of 1999
Stir of Echoes 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

30
76 58
Cruel Intentions is listed (or ranked) 30 on the list The Best Movies of 1999
Cruel Intentions 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

31
53 63
The Thomas Crown Affair is listed (or ranked) 31 on the list The Best Movies of 1999
The Thomas Crown Affair Pierce Brosnan, Faye Dunaway, Rene Russo The Thomas Crown Affair is a 1999 American heist 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. ...more

32
86 62
Girl, Interrupted is listed (or ranked) 32 on the list The Best Movies of 1999
Girl, Interrupted 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

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60 58
Analyze This is listed (or ranked) 33 on the list The Best Movies of 1999
Analyze This Robert De Niro, Billy Crystal, Lisa Kudrow Analyze This is a 1999 gangster 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 ...more

34
65 52
Election is listed (or ranked) 34 on the list The Best Movies of 1999
Election 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

35
41 58
Arlington Road is listed (or ranked) 35 on the list The Best Movies of 1999
Arlington Road 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

36
55 53
The Hurricane is listed (or ranked) 36 on the list The Best Movies of 1999
The Hurricane 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

37
58 60
Varsity Blues is listed (or ranked) 37 on the list The Best Movies of 1999
Varsity Blues 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

38
55 59
Man on the Moon is listed (or ranked) 38 on the list The Best Movies of 1999
Man on the Moon 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

39
66 64
Tarzan is listed (or ranked) 39 on the list The Best Movies of 1999
Tarzan 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
43 55
Go is listed (or ranked) 40 on the list The Best Movies of 1999
Go Katie Holmes, Melissa McCarthy, Timothy Olyphant Go is a 1999 crime comedy film written by John August and directed by Doug Liman, with three intertwining plots that happen to involve one drug deal. The film stars William Fichtner, Katie ...more

41
54 60
Boys Don't Cry is listed (or ranked) 41 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

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63 45
Double Jeopardy is listed (or ranked) 42 on the list The Best Movies of 1999
Double Jeopardy 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 for ...more

43
77 84
The Blair Witch Project is listed (or ranked) 43 on the list The Best Movies of 1999
The Blair Witch Project 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

44
38 47
October Sky is listed (or ranked) 44 on the list The Best Movies of 1999
October Sky 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
56 62
She's All That is listed (or ranked) 45 on the list The Best Movies of 1999
She's All That Sarah Michelle Gellar, Anna Paquin, Lil' Kim She's All That is a 1999 American teen romantic comedy film directed by Robert Iscove and starring Freddie Prinze, Jr. and Rachael Leigh Cook. It is a modern adaptation of George Bernard Shaw's ...more

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47 52
The Virgin Suicides is listed (or ranked) 46 on the list The Best Movies of 1999
The Virgin Suicides Kirsten Dunst, Kathleen Turner, Danny DeVito The Virgin Suicides 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 ...more

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40 47
The Cider House Rules is listed (or ranked) 47 on the list The Best Movies of 1999
wiabux added The Cider House Rules Charlize Theron, Michael Caine, Paul Rudd The Cider House Rules is a 1999 American drama film directed by Lasse Hallström, based on John Irving's novel of the same name. The film won two Academy Awards, and was nominated for the ...more

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26 32
The Straight Story is listed (or ranked) 48 on the list The Best Movies of 1999
weik added The Straight Story 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

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44 42
Deep Blue Sea is listed (or ranked) 49 on the list The Best Movies of 1999
looksharp added Deep Blue Sea 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

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51 46
Payback is listed (or ranked) 50 on the list The Best Movies of 1999
Payback Mel Gibson, Lucy Liu, Maria Bello Payback is a 1999 American action crime 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. ...more