2019 Movies Turning 20 in 2019  

Ranker Film
10.5k votes 452 voters 3.6k 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
180 68
Fight Club is listed (or ranked) 1 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

2
174 65
The Green Mile is listed (or ranked) 2 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

3
165 60
The Matrix is listed (or ranked) 3 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

4
174 71
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
155 70
American Pie is listed (or ranked) 5 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

6
133 57
Cruel Intentions is listed (or ranked) 6 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

7
145 72
The Boondock Saints is listed (or ranked) 7 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

8
140 70
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
133 68
The Sixth Sense is listed (or ranked) 9 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

10
145 80
Dogma is listed (or ranked) 10 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

11
135 73
The Mummy is listed (or ranked) 11 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

12
126 69
Toy Story 2 is listed (or ranked) 12 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

13
124 80
Varsity Blues is listed (or ranked) 13 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

14
127 83
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
112 70
Big Daddy is listed (or ranked) 15 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

16
104 76
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
92 85
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
81 77
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
86 86
Galaxy Quest is listed (or ranked) 19 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

20
66 62
She's All That is listed (or ranked) 20 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

21
60 56
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
61 59
The Bone Collector is listed (or ranked) 22 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

23
67 72
The Iron Giant is listed (or ranked) 23 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

24
54 58
Double Jeopardy is listed (or ranked) 24 on the list Movies Turning 20 in 2019
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.

25
56 63
Three Kings is listed (or ranked) 25 on the list Movies Turning 20 in 2019
George Clooney, Mark Wahlberg, Ice Cube
Three Kings is a 1999 satirical comedy film written and directed by David O. Russell from a story by John Ridley about a men taking gold that takes place during the 1991 Iraqi uprising against ...more