Nostalgia Movies Turning 20 in 2019  

Ranker Film
12.4k votes 542 voters 5k views 114 items

List Rules Vote up the movies that came out in 1999 that you still enjoy today.

Take a trip down memory lane with this list of movies turning 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 turning 20 years old this year?  

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.

list ordered by

1
204 74
The Matrix is listed (or ranked) 1 on the list Movies Turning 20 in 2019
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
211 79
Fight Club is listed (or ranked) 2 on the list Movies Turning 20 in 2019
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
202 77
The Green Mile is listed (or ranked) 3 on the list Movies Turning 20 in 2019
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

4
201 82
Office Space is listed (or ranked) 4 on the list Movies Turning 20 in 2019
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

5
160 69
Cruel Intentions is listed (or ranked) 5 on the list Movies Turning 20 in 2019
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

6
168 75
The Sixth Sense is listed (or ranked) 6 on the list Movies Turning 20 in 2019
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

7
177 85
American Pie is listed (or ranked) 7 on the list Movies Turning 20 in 2019
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

8
174 83
10 Things I Hate About You is listed (or ranked) 8 on the list Movies Turning 20 in 2019
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

9
164 84
The Mummy is listed (or ranked) 9 on the list Movies Turning 20 in 2019
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

10
165 86
The Boondock Saints is listed (or ranked) 10 on the list Movies Turning 20 in 2019
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

11
153 82
Toy Story 2 is listed (or ranked) 11 on the list Movies Turning 20 in 2019
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

12
164 95
Dogma is listed (or ranked) 12 on the list Movies Turning 20 in 2019
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

13
140 83
Big Daddy is listed (or ranked) 13 on the list Movies Turning 20 in 2019
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

14
151 96
Austin Powers: The Spy Who Sha... is listed (or ranked) 14 on the list Movies Turning 20 in 2019
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
139 90
Varsity Blues is listed (or ranked) 15 on the list Movies Turning 20 in 2019
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

16
126 89
American Beauty is listed (or ranked) 16 on the list Movies Turning 20 in 2019
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

17
111 100
South Park: Bigger, Longer & U... is listed (or ranked) 17 on the list Movies Turning 20 in 2019
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

18
102 90
Sleepy Hollow is listed (or ranked) 18 on the list Movies Turning 20 in 2019
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

19
87 74
She's All That is listed (or ranked) 19 on the list Movies Turning 20 in 2019
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

20
106 97
Galaxy Quest is listed (or ranked) 20 on the list Movies Turning 20 in 2019
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

21
76 66
Blast from the Past is listed (or ranked) 21 on the list Movies Turning 20 in 2019
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

22
76 72
Never Been Kissed is listed (or ranked) 22 on the list Movies Turning 20 in 2019
Jessica Alba, Drew Barrymore, James Franco
Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew Barrymore's production company, Flower Films, directed by Raja Gosnell and starring Drew Barrymore, David ...more

23
71 74
The Bone Collector is listed (or ranked) 23 on the list Movies Turning 20 in 2019
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

24
80 86
The Iron Giant is listed (or ranked) 24 on the list Movies Turning 20 in 2019
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

25
64 70
Being John Malkovich is listed (or ranked) 25 on the list Movies Turning 20 in 2019
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