2019 Movies Turning 20 in 2019  

Ranker Film
372 votes 10 voters 114 items

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
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Toy Story 2 is listed (or ranked) 1 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

2
6 2
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
5 1
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
5 1
Austin Powers: The Spy Who Sha... is listed (or ranked) 4 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

5
5 1
The Green Mile is listed (or ranked) 5 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

6
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The World Is Not Enough is listed (or ranked) 6 on the list Movies Turning 20 in 2019
Pierce Brosnan, Denise Richards, John Cleese The World Is Not Enough is the nineteenth spy film in the James Bond series, and the third to star Pierce Brosnan as the fictional MI6 agent James Bond. The film was directed by Michael Apted, ...more

7
5 2
The Iron Giant is listed (or ranked) 7 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

8
4 2
The Mummy is listed (or ranked) 8 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

9
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American Beauty is listed (or ranked) 9 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

10
4 2
Tarzan is listed (or ranked) 10 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

11
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Star Wars Episode I: The Phant... is listed (or ranked) 11 on the list Movies Turning 20 in 2019
Natalie Portman, Keira Knightley, Ewan McGregor (32 Years Before Episode IV) Stranded on the desert planet Tatooine after rescuing young Queen Amidala from the impending invasion of Naboo, Jedi apprentice Obi-Wan Kenobi and his Jedi Master ...more

12
3 1
Sleepy Hollow is listed (or ranked) 12 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

13
3 1
October Sky is listed (or ranked) 13 on the list Movies Turning 20 in 2019
Jake Gyllenhaal, Laura Dern, Chris Cooper October Sky is a 1999 American biographical film directed by Joe Johnston, starring Jake Gyllenhaal, Chris Cooper and Laura Dern. It is based on the true story of Homer Hickam, a coal miner's ...more

14
3 1
The Boondock Saints is listed (or ranked) 14 on the list Movies Turning 20 in 2019
Willem Dafoe, Norman Reedus, Billy Connolly The Boondock Saints is a 1999 American crime film written and directed by Troy Duffy. The film stars Sean Patrick Flanery and Norman Reedus as fraternal twins, Connor and Murphy MacManus, who ...more

15
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Doug's 1st Movie is listed (or ranked) 15 on the list Movies Turning 20 in 2019
Frank Welker, Fred Newman, Fran Brill Doug's 1st Movie is a 1999 animated film based on the Disney version of the Nickelodeon television series Doug. The film was directed by Maurice Joyce, and stars the regular television cast of ...more

16
3 2
Man on the Moon is listed (or ranked) 16 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

17
2 1
Bartok the Magnificent is listed (or ranked) 17 on the list Movies Turning 20 in 2019
Kelsey Grammer, Tim Curry, Jennifer Tilly Bartok the Magnificent, directed by Don Bluth and Gary Goldman, is a 1999 direct-to-video spin-off to the 1997 film Anastasia, which features Hank Azaria as the voice of Bartok, Kelsey Grammer ...more

18
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Mystery Men is listed (or ranked) 18 on the list Movies Turning 20 in 2019
Ben Stiller, Tom Waits, Hank Azaria Mystery Men is a 1999 American superhero comedy film directed by Kinka Usher and written by Neil Cuthbert and Bob Burden, loosely based on Burden's Flaming Carrot Comics, and starring Hank ...more

19
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Wild Wild West is listed (or ranked) 19 on the list Movies Turning 20 in 2019
Salma Hayek, Will Smith, Kevin Kline Wild Wild West is a 1999 American steampunk western action-comedy film directed by Barry Sonnenfeld. A big-screen adaptation of the 1965–1969 TV series The Wild Wild West, it stars Will Smith, ...more

20
3 3
Dogma is listed (or ranked) 20 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

21
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The Thomas Crown Affair is listed (or ranked) 21 on the list Movies Turning 20 in 2019
Pierce Brosnan, Faye Dunaway, Rene Russo The Thomas Crown Affair is a 1999 American heist film directed by John McTiernan. The film, starring Pierce Brosnan, Rene Russo and Denis Leary, is a remake of the 1968 film of the same name. ...more

22
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Magnolia is listed (or ranked) 22 on the list Movies Turning 20 in 2019
Tom Cruise, Julianne Moore, Philip Seymour Hoffman Magnolia is a 1999 American drama film written, produced, and directed by Paul Thomas Anderson and starring Jeremy Blackman, Tom Cruise, Philip Baker Hall, Philip Seymour Hoffman, Ricky Jay, ...more

23
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Blast from the Past is listed (or ranked) 23 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

24
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Arlington Road is listed (or ranked) 24 on the list Movies Turning 20 in 2019
Jeff Bridges, Tim Robbins, Joan Cusack Arlington Road is a 1999 American mystery thriller film, which tells the story of a widowed George Washington University professor who suspects his new neighbors are involved in terrorism and ...more

25
3 3
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
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The Matrix is listed (or ranked) 26 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

27
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American Pie is listed (or ranked) 27 on the list Movies Turning 20 in 2019
Alyson Hannigan, Tara Reid, Shannon Elizabeth American Pie is a 1999 teen sex 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 ...more

28
3 3
The Sixth Sense is listed (or ranked) 28 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, a troubled, isolated boy who is able to see and ...more

29
2 2
The Ninth Gate is listed (or ranked) 29 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

30
2 2
Galaxy Quest is listed (or ranked) 30 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

31
2 2
The Virgin Suicides is listed (or ranked) 31 on the list Movies Turning 20 in 2019
Kirsten Dunst, Kathleen Turner, Danny DeVito The Virgin Suicides 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 ...more

32
2 2
Fantasia 2000 is listed (or ranked) 32 on the list Movies Turning 20 in 2019
Steve Martin, Bette Midler, James Earl Jones Fantasia 2000 is a 1999 American animated anthology film produced by Walt Disney Feature Animation and released by Walt Disney Pictures. It is the 38th film in the Walt Disney Animated Classics ...more

33
2 2
The Insider is listed (or ranked) 33 on the list Movies Turning 20 in 2019
Al Pacino, Russell Crowe, Christopher Plummer The Insider is a 1999 American drama film directed by Michael Mann, based on the true story of a 60 Minutes segment about Jeffrey Wigand, a whistleblower in the tobacco industry. The 60 Minutes ...more

34
2 2
Notting Hill is listed (or ranked) 34 on the list Movies Turning 20 in 2019
Julia Roberts, Alec Baldwin, Mischa Barton Notting Hill is a 1999 British romantic comedy film set in Notting Hill, London, released on 21 May 1999. The screenplay was by Richard Curtis, who had written Four Weddings and a Funeral, and ...more

35
2 2
Any Given Sunday is listed (or ranked) 35 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

36
2 2
Deep Blue Sea is listed (or ranked) 36 on the list Movies Turning 20 in 2019
Samuel L. Jackson, LL Cool J, Thomas Jane Deep Blue Sea is a 1999 science fiction horror film, starring Saffron Burrows, Thomas Jane, LL Cool J, Michael Rapaport, Stellan Skarsgård and Samuel L. Jackson. The film was directed by ...more

37
2 2
Big Daddy is listed (or ranked) 37 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

38
2 2
Stigmata is listed (or ranked) 38 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

39
1 1
She's All That is listed (or ranked) 39 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

40
1 1
The Cider House Rules is listed (or ranked) 40 on the list Movies Turning 20 in 2019
Charlize Theron, Michael Caine, Paul Rudd The Cider House Rules is a 1999 American drama film directed by Lasse Hallström, based on John Irving's novel of the same name. The film won two Academy Awards, and was nominated for the ...more

41
1 1
Runaway Bride is listed (or ranked) 41 on the list Movies Turning 20 in 2019
Julia Roberts, Richard Gere, Christopher Meloni Runaway Bride is a 1999 American romantic comedy film directed by Garry Marshall, and stars Julia Roberts and Richard Gere.The screenplay was written by Josann McGibbon, Sara Parriott and Audrey ...more

42
1 1
The Blair Witch Project is listed (or ranked) 42 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

43
1 1
The Bone Collector is listed (or ranked) 43 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 crime ...more

44
1 1
Play It to the Bone is listed (or ranked) 44 on the list Movies Turning 20 in 2019
Mike Tyson, Lucy Liu, Kevin Costner Play It to the Bone is a 1999 sports/comedy-drama film, starring Antonio Banderas and Woody Harrelson, written and directed by Ron Shelton. It follows the adventures of two boxers and best ...more

45
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Never Been Kissed is listed (or ranked) 45 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

46
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Bringing Out the Dead is listed (or ranked) 46 on the list Movies Turning 20 in 2019
Nicolas Cage, Queen Latifah, John Goodman Bringing Out the Dead is a 1999 American drama film directed by Martin Scorsese and written by Paul Schrader, based on the novel by Joe Connelly. It stars Nicolas Cage, Patricia Arquette, John ...more

47
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Whiteboyz is listed (or ranked) 47 on the list Movies Turning 20 in 2019
Dr. Dre, Piper Perabo, Fat Joe Whiteboyz is a 1999 American film. The independent, limited release was written by Danny Hoch, Garth Belcon, Henri M. Kessler, Richard Stratton, and Marc Levin, and directed by Levin. The film ...more

48
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My Favorite Martian is listed (or ranked) 48 on the list Movies Turning 20 in 2019
Elizabeth Hurley, Christopher Lloyd, Daryl Hannah My Favorite Martian is a 1999 comic science fiction film starring Christopher Lloyd, Jeff Daniels, Daryl Hannah, Elizabeth Hurley, Wallace Shawn and Ray Walston, based on the 1960s television ...more

49
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Fantasia is listed (or ranked) 49 on the list Movies Turning 20 in 2019
Walt Disney, Corey Burton, Leopold Stokowski Fantasia is a 1940 American animated film produced by Walt Disney and released by Walt Disney Productions. With story direction by Joe Grant and Dick Huemer, and production supervision by Ben ...more

50
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8mm is listed (or ranked) 50 on the list Movies Turning 20 in 2019
Nicolas Cage, Joaquin Phoenix, James Gandolfini 8mm is a 1999 American-German crime 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 ...more