2019 Movies Turning 20 in 2019  

Ranker Film
1.9k votes 60 voters 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
27 7
Varsity Blues is listed (or ranked) 1 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

2
27 7
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
27 9
Office Space is listed (or ranked) 3 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

4
29 11
Fight Club is listed (or ranked) 4 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

5
27 12
Toy Story 2 is listed (or ranked) 5 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

6
20 7
The Matrix is listed (or ranked) 6 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

7
21 8
Dogma is listed (or ranked) 7 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

8
24 11
American Pie is listed (or ranked) 8 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

9
20 9
The Boondock Saints is listed (or ranked) 9 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

10
21 11
Austin Powers: The Spy Who Sha... is listed (or ranked) 10 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

11
18 10
The Sixth Sense is listed (or ranked) 11 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

12
19 11
10 Things I Hate About You is listed (or ranked) 12 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

13
15 8
Any Given Sunday is listed (or ranked) 13 on the list Movies Turning 20 in 2019
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

14
18 11
Galaxy Quest is listed (or ranked) 14 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

15
19 12
The Mummy is listed (or ranked) 15 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

16
10 5
Never Been Kissed is listed (or ranked) 16 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

17
15 11
Cruel Intentions is listed (or ranked) 17 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

18
14 10
Blast from the Past is listed (or ranked) 18 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

19
11 7
Stigmata is listed (or ranked) 19 on the list Movies Turning 20 in 2019
Portia de Rossi, Patricia Arquette, Nia Long Stigmata is a 1999 supernatural horror film directed by Rupert Wainwright and starring Patricia Arquette as an atheist hairdresser from Pittsburgh, Pennsylvania, who is afflicted with the ...more

20
16 13
American Beauty is listed (or ranked) 20 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

21
14 12
Three Kings is listed (or ranked) 21 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

22
9 7
Detroit Rock City is listed (or ranked) 22 on the list Movies Turning 20 in 2019
Emmanuelle Chriqui, Edward Furlong, Gene Simmons Detroit Rock City is a 1999 American comedy film directed by Adam Rifkin and written by Carl V. Dupré. It tells of four teenage boys in a KISS cover band who try to see their idols in ...more

23
9 7
Mystery, Alaska is listed (or ranked) 23 on the list Movies Turning 20 in 2019
Russell Crowe, Mike Myers, Burt Reynolds Mystery, Alaska is a 1999 comedy-drama film directed by Jay Roach about an amateur ice hockey team, from the fictional small-town of Mystery, that plays an exhibition game against the New York ...more

24
15 14
Big Daddy is listed (or ranked) 24 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

25
14 13
South Park: Bigger, Longer & U... is listed (or ranked) 25 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

26
12 11
Double Jeopardy is listed (or ranked) 26 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.

27
12 11
Sleepy Hollow is listed (or ranked) 27 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

28
11 10
She's All That is listed (or ranked) 28 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

29
9 8
Analyze This is listed (or ranked) 29 on the list Movies Turning 20 in 2019
Robert De Niro, Billy Crystal, Lisa Kudrow Analyze This is a 1999 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 Billy ...more

30
9 8
Stir of Echoes is listed (or ranked) 30 on the list Movies Turning 20 in 2019
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

31
8 7
The General's Daughter is listed (or ranked) 31 on the list Movies Turning 20 in 2019
John Travolta, James Woods, Madeleine Stowe The General's Daughter is a 1999 film directed by Simon West starring John Travolta. The plot concerns the mysterious happenings of the daughter of a prominent general. The movie is based on the ...more

32
6 5
Brokedown Palace is listed (or ranked) 32 on the list Movies Turning 20 in 2019
Kate Beckinsale, Claire Danes, Paul Walker Brokedown Palace is a 1999 American drama film directed by Jonathan Kaplan, and starring Claire Danes, Kate Beckinsale, Bill Pullman and Lim Kay Tong. It deals with two American friends ...more

33
13 13
Man on the Moon is listed (or ranked) 33 on the list Movies Turning 20 in 2019
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

34
12 12
Tarzan is listed (or ranked) 34 on the list Movies Turning 20 in 2019
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

35
11 11
The Iron Giant is listed (or ranked) 35 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

36
10 10
Deuce Bigalow: Male Gigolo is listed (or ranked) 36 on the list Movies Turning 20 in 2019
Adam Sandler, Amy Poehler, Rob Schneider Deuce Bigalow: Male Gigolo is a 1999 comedy film starring Rob Schneider, William Forsythe, Eddie Griffin, Oded Fehr and Arija Bareikis. The film follows a hapless fishtank cleaner who goes into ...more

37
8 9
Girl, Interrupted is listed (or ranked) 37 on the list Movies Turning 20 in 2019
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

38
7 8
Boys Don't Cry is listed (or ranked) 38 on the list Movies Turning 20 in 2019
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

39
7 8
Being John Malkovich is listed (or ranked) 39 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

40
7 8
The Talented Mr. Ripley is listed (or ranked) 40 on the list Movies Turning 20 in 2019
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

41
6 7
For Love of the Game is listed (or ranked) 41 on the list Movies Turning 20 in 2019
Kevin Costner, Kelly Preston, J.K. Simmons For Love of the Game is a 1999 American drama sports film based on the novel of the same title by Michael Shaara. It is directed by Sam Raimi and stars Kevin Costner and Kelly Preston. The film ...more

42
6 7
The Ninth Gate is listed (or ranked) 42 on the list Movies Turning 20 in 2019
Johnny Depp, Frank Langella, Lena Olin The Ninth Gate is a 1999 French-Spanish-American thriller film directed, produced, and co-written by Roman Polanski. The film is loosely based upon Arturo Pérez-Reverte's 1993 novel The ...more

43
5 6
8mm is listed (or ranked) 43 on the list Movies Turning 20 in 2019
Nicolas Cage, Joaquin Phoenix, James Gandolfini 8mm is a 1999 American-German mystery thriller film directed by Joel Schumacher and written by Andrew Kevin Walker. The film stars Nicolas Cage as a private investigator who delves into the ...more

44
9 11
Summer of Sam is listed (or ranked) 44 on the list Movies Turning 20 in 2019
Mira Sorvino, Jennifer Esposito, Adrien Brody Summer of Sam is a 1999 American thriller film that recounts the Son of Sam. It was directed and produced by Spike Lee and stars John Leguizamo, Adrien Brody, Mira Sorvino, and Jennifer

45
8 10
Go is listed (or ranked) 45 on the list Movies Turning 20 in 2019
Katie Holmes, Melissa McCarthy, Timothy Olyphant Go is a 1999 comedy film written by John August and directed by Doug Liman, with three intertwining plots that happen to involve one deal. The film stars William Fichtner, Katie Holmes, Jay ...more

46
8 10
The Virgin Suicides is listed (or ranked) 46 on the list Movies Turning 20 in 2019
Kirsten Dunst, Kathleen Turner, Danny DeVito The film 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 Hartnett, and A. ...more

47
8 10
Election is listed (or ranked) 47 on the list Movies Turning 20 in 2019
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

48
8 10
The Blair Witch Project is listed (or ranked) 48 on the list Movies Turning 20 in 2019
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

49
8 10
The Hurricane is listed (or ranked) 49 on the list Movies Turning 20 in 2019
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

50
5 7
House on Haunted Hill is listed (or ranked) 50 on the list Movies Turning 20 in 2019
Ali Larter, Famke Janssen, Geoffrey Rush House on Haunted Hill is a 1999 American horror film, directed by William Malone and starring Geoffrey Rush, Famke Janssen, Taye Diggs, Ali Larter and Jeffrey Combs. It also includes a cameo ...more