Jason BancroftList RulesVote up the movies that came out in 1999 that you still enjoy today.
Take a trip down memory lane with this list of movies that turned 20 in 2019. Featuring epic war dramas, cult classics, well-made comedies, and some of the greatest movies of all time, the best 1999 films will remind you how well older movies have aged (or not) throughout the decades. What is your favorite movie that turned 20 years old in 2019?
When ranking the movies that came out 20 years ago, you can expect to see movies that are classics, like The Matrix, Fight Club, and Office Space, at the top. Other memorable 1999 movies include Magnolia, The Sixth Sense, Iron Giant, The Mummy, and The Talented Mr. Ripley.
While American Beauty won Best Picture at the 72nd Academy Awards, the 1999 Oscars celebrated other great films such as Being John Malkovich, Cider House Rules, Boys Don't Cry, and The Green Mile.
Vote up the best films released in 1999, and celebrate these movies turning 20 with another rewatch.
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467133Austin 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
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484213The 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... more3
345139South 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... more4
481243Dogma
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... more5
659356The 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... more6
388194American 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... more7
618340The 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... more8
233117Cruel 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,... more9
196110Three 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... more10
400270Varsity Blues
Ali Larter, Paul WalkerReleased: 1999
Directed by: Brian Robbins
Varsity Blues is a 1999 American coming-of-age sports comedy-drama film directed by Brian... more11
248152Star Wars Episode I: The Phantom Menace
Natalie Portman, Keira KnightleyReleased: 1999
Directed by: George Lucas
(32 Years Before Episode IV) Stranded on the desert planet Tatooine after rescuing young Queen... more12
17597Girl, 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... more13
211132The Blair Witch Project
Heather Donahue, Joshua LeonardReleased: 1999
Directed by: Daniel Myrick, Eduardo Sánchez
The Blair Witch Project is a 1999 American found footage horror film written, directed and... more14
202125Wild Wild West
Salma Hayek, Will SmithReleased: 1999
Directed by: Barry Sonnenfeld
Wild Wild West is a 1999 American steampunk western action-comedy film directed by Barry... more15
16599Analyze This
Robert De Niro, Billy CrystalReleased: 1999
Directed by: Harold Ramis
Analyze This is a 1999 comedy film directed by Harold Ramis, who co-wrote the screenplay with... more16
15089Mystery Men
Ben Stiller, Tom WaitsReleased: 1999
Directed by: Kinka Usher
Mystery Men is a 1999 American superhero comedy film directed by Kinka Usher and written by... more17
164106Never Been Kissed
Jessica Alba, Drew BarrymoreReleased: 1999
Directed by: Raja Gosnell
Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew... more18
343275Galaxy 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... more19
13085The World Is Not Enough
Pierce Brosnan, Denise RichardsReleased: 1999
Directed by: Michael Apted
The World Is Not Enough is the nineteenth spy film in the James Bond series, and the third to... more20
13798Stigmata
Portia de Rossi, Patricia ArquetteReleased: 1999
Directed by: Rupert Wainwright
Stigmata is a 1999 supernatural horror film directed by Rupert Wainwright and starring... more21
152113Man on the Moon
Courtney Love, Jim CarreyReleased: 1999
Directed by: Miloš Forman
Man on the Moon is a 1999 American biographical comedy–drama film about the late American... more22
11382The 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... more23
10678Boys Don't Cry
Hilary Swank, Chloë SevignyReleased: 1999
Directed by: Kimberly Peirce
Boys Don't Cry is a 1999 American independent romantic drama film directed by Kimberly Peirce... more24
10476Entrapment
Catherine Zeta-Jones, Sean ConneryReleased: 1999
Directed by: Jon Amiel
Entrapment is a 1999 American caper film directed by Jon Amiel and starring Sean Connery and... more25
282255Office 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
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