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
433236The Sixth Sense
Bruce Willis, Mischa BartonReleased: 1999
Directed by: M. Night Shyamalan
The Sixth Sense is a 1999 American supernatural thriller film written and directed by M. Night... more on Wikipedia
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363192Toy Story 2
Tom Hanks, Kelsey GrammerReleased: 1999
Directed by: John Lasseter, Lee Unkrich, Ash Brannon
Toy Story 2 is a 1999 American computer-animated comedy adventure film produced by Pixar... more on Wikipedia3
27412710 Things I Hate About You
Joseph Gordon-Levitt, Gabrielle UnionReleased: 1999
Directed by: Gil Junger
10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and... more on Wikipedia4
300158Office Space
Jennifer Aniston, John C. McGinleyReleased: 1999
Directed by: Mike Judge
Office Space is a 1999 American comedy film written and directed by Mike Judge. The film... more on Wikipedia5
398264The Green Mile
Tom Hanks, Gary SiniseReleased: 1999
Directed by: Frank Darabont
The Green Mile is a 1999 American fantasy drama film directed by Frank Darabont and adapted... more on Wikipedia6
561400Fight Club
Brad Pitt, Jared LetoReleased: 1999
Directed by: David Fincher
Fight Club is a 1999 film based on the 1996 novel of the same name by Chuck Palahniuk. The... more on Wikipedia7
359253American Beauty
Kevin Spacey, Annette BeningReleased: 1999
Directed by: Sam Mendes
American Beauty is a 1999 American drama film directed by Sam Mendes. An advertising executive... more on Wikipedia8
533429The Matrix
Keanu Reeves, Hugo WeavingReleased: 1999
Directed by: Andy Wachowski, Lana Wachowski
The Matrix is a 1999 American-Australian science fiction action film written and directed by... more on Wikipedia9
183101Cruel Intentions
Reese Witherspoon, Sarah Michelle GellarReleased: 1999
Directed by: Roger Kumble
Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe,... more on Wikipedia10
286195The Mummy
Rachel Weisz, Brendan FraserReleased: 1999
Directed by: Stephen Sommers
The Mummy is a 1999 American fantasy adventure film written and directed by Stephen Sommers... more on Wikipedia11
234169Sleepy Hollow
Johnny Depp, Christina RicciReleased: 1999
Directed by: Tim Burton
Sleepy Hollow is a 1999 American fantasy horror adventure film directed by Tim Burton. It is a... more on Wikipedia12
245180Austin Powers: The Spy Who Shagged Me
Elizabeth Hurley, Heather GrahamReleased: 1999
Directed by: Jay Roach
Austin Powers: The Spy Who Shagged Me is a 1999 action comedy film and the second film in the... more on Wikipedia13
230188Being John Malkovich
Cameron Diaz, Brad PittReleased: 1999
Directed by: Spike Jonze
Being John Malkovich is a 1999 American fantasy comedy film written by Charlie Kaufman and... more on Wikipedia14
187125Galaxy Quest
Sigourney Weaver, Alan RickmanReleased: 1999
Directed by: Dean Parisot
Galaxy Quest is a 1999 American science fiction action comedy film directed by Dean Parisot... more on Wikipedia15
166123The Boondock Saints
Willem Dafoe, Norman ReedusReleased: 1999
Directed by: Troy Duffy
The Boondock Saints is a 1999 American film written and directed by Troy Duffy. The film stars... more on Wikipedia16
167101Girl, Interrupted
Angelina Jolie, Winona RyderReleased: 1999
Directed by: James Mangold
Girl, Interrupted is a 1999 American drama film, and an adaptation of Susanna Kaysen's 1993... more on Wikipedia17
140100Election
Reese Witherspoon, Matthew BroderickReleased: 1999
Directed by: Alexander Payne
Election is a 1999 American comedy film directed and written by Alexander Payne and adapted by... more on Wikipedia18
193123South Park: Bigger, Longer & Uncut
George Clooney, Minnie DriverReleased: 1999
Directed by: Trey Parker
South Park: Bigger, Longer & Uncut is a 1999 American adult animated satirical musical comedy... more on Wikipedia19
211183Eyes Wide Shut
Tom Cruise, Nicole KidmanReleased: 1999
Directed by: Stanley Kubrick
Eyes Wide Shut is a 1999 American thriller film loosely based upon Arthur Schnitzler's 1926... more on Wikipedia20
206176Magnolia
Tom Cruise, Julianne MooreReleased: 1999
Directed by: Paul Thomas Anderson
Magnolia is a 1999 American drama film written, produced, and directed by Paul Thomas Anderson... more on Wikipedia21
206178The Iron Giant
Jennifer Aniston, Vin DieselReleased: 1999
Directed by: Brad Bird
The Iron Giant is a 1999 American animated science fiction comedy-drama film using both... more on Wikipedia22
12079Double Jeopardy
Ashley Judd, Tommy Lee JonesReleased: 1999
Directed by: Bruce Beresford
Double Jeopardy is a 1999 American mystery-thriller film directed by Bruce Beresford and... more on Wikipedia23
177157Dogma
Ben Affleck, Matt DamonReleased: 1999
Directed by: Kevin Smith
Dogma is a 1999 American comedy film written and directed by Kevin Smith. The existence of... more on Wikipedia24
158137Three Kings
George Clooney, Mark WahlbergReleased: 1999
Directed by: David O. Russell
Three Kings is a 1999 satirical comedy film written and directed by David O. Russell from a... more on Wikipedia25
172160The Talented Mr. Ripley
Gwyneth Paltrow, Cate BlanchettReleased: 1999
Directed by: Anthony Minghella
The Talented Mr. Ripley is a 1999 American psychological thriller written for the screen and... more on Wikipedia
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