2019 Movies Turning 20 in 2019  

Ranker Film
510 votes 12 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
9 1
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 1
Office Space is listed (or ranked) 2 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

3
6 2
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
6 2
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
6 3
Fight Club is listed (or ranked) 5 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

6
5 3
The Mummy is listed (or ranked) 6 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

7
5 3
American Beauty is listed (or ranked) 7 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

8
5 3
Tarzan is listed (or ranked) 8 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

9
4 2
Galaxy Quest is listed (or ranked) 9 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

10
4 2
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
4 2
The World Is Not Enough is listed (or ranked) 11 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

12
3 1
Doug's 1st Movie is listed (or ranked) 12 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

13
5 4
The Iron Giant is listed (or ranked) 13 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

14
4 3
Man on the Moon is listed (or ranked) 14 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

15
2 1
Mystery Men is listed (or ranked) 15 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

16
2 1
Wild Wild West is listed (or ranked) 16 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

17
1 0
Never Been Kissed is listed (or ranked) 17 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

18
4 4
Dogma is listed (or ranked) 18 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

19
4 4
Blast from the Past is listed (or ranked) 19 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

20
4 4
Star Wars Episode I: The Phant... is listed (or ranked) 20 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

21
4 4
South Park: Bigger, Longer & U... is listed (or ranked) 21 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

22
4 4
American Pie is listed (or ranked) 22 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

23
3 3
October Sky is listed (or ranked) 23 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

24
3 3
Sleepy Hollow is listed (or ranked) 24 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

25
3 3
Notting Hill is listed (or ranked) 25 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 and the film was produced by Duncan Kenworthy and ...more

26
3 3
EDtv is listed (or ranked) 26 on the list Movies Turning 20 in 2019
Matthew McConaughey, Elizabeth Hurley, Ellen DeGeneres EDtv is a 1999 American satirical comedy film directed by Ron Howard. An adaptation of the Quebec film Louis 19, le roi des ondes, it stars Matthew McConaughey, Jenna Elfman, Woody Harrelson, ...more

27
2 2
Double Jeopardy is listed (or ranked) 27 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 for ...more

28
2 2
Stigmata is listed (or ranked) 28 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

29
2 2
Runaway Bride is listed (or ranked) 29 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

30
2 2
The Bone Collector is listed (or ranked) 30 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

31
2 2
Deep Blue Sea is listed (or ranked) 31 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

32
2 2
She's All That is listed (or ranked) 32 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

33
2 2
Any Given Sunday is listed (or ranked) 33 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

34
1 1
My Favorite Martian is listed (or ranked) 34 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

35
1 1
Dick is listed (or ranked) 35 on the list Movies Turning 20 in 2019
Kirsten Dunst, Will Ferrell, Ryan Reynolds Dick is a 1999 American comedy film directed by Andrew Fleming from a script he wrote with Sheryl Longin. It is a parody retelling the events of the Watergate scandal which ended the presidency ...more

36
1 1
The Other Sister is listed (or ranked) 36 on the list Movies Turning 20 in 2019
Diane Keaton, Poppy Montgomery, Juliette Lewis The Other Sister is a 1999 American romantic comedy film directed by Garry Marshall and stars Juliette Lewis, Giovanni Ribisi, Diane Keaton, and Tom Skerritt. It was filmed in Long Beach, ...more

37
1 1
The Out-of-Towners is listed (or ranked) 37 on the list Movies Turning 20 in 2019
Goldie Hawn, Steve Martin, John Cleese The Out-of-Towners is a 1999 comedy film starring Steve Martin and Goldie Hawn. The movie is a remake of a 1970 film by the same name; the original version, written by Neil Simon, starred Jack ...more

38
3 4
10 Things I Hate About You is listed (or ranked) 38 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

39
3 4
Summer of Sam is listed (or ranked) 39 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

40
3 4
Election is listed (or ranked) 40 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

41
2 3
Bartok the Magnificent is listed (or ranked) 41 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

42
2 3
Entrapment is listed (or ranked) 42 on the list Movies Turning 20 in 2019
Catherine Zeta-Jones, Sean Connery, Ving Rhames Entrapment is a 1999 American caper film directed by Jon Amiel and starring Sean Connery and Catherine Zeta-Jones.

43
2 3
Deuce Bigalow: Male Gigolo is listed (or ranked) 43 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

44
2 3
Big Daddy is listed (or ranked) 44 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

45
2 3
Being John Malkovich is listed (or ranked) 45 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

46
1 2
The Cider House Rules is listed (or ranked) 46 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

47
1 2
Anna and the King is listed (or ranked) 47 on the list Movies Turning 20 in 2019
Jodie Foster, Bai Ling, Tom Felton Anna and the King is a 1999 biographical drama film loosely based on the 1944 novel Anna and the King of Siam, which give a fictionalised account of the diaries of Anna Leonowens. The story ...more

48
0 1
Mumford is listed (or ranked) 48 on the list Movies Turning 20 in 2019
Zooey Deschanel, Kelly Monaco, Martin Short Mumford is a 1999 American comedy-drama film written and directed by Lawrence Kasdan. It is set in a small town where a new psychologist gives offbeat advice to the neurotic residents. Both the ...more

49
0 1
Whiteboyz is listed (or ranked) 49 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

50
0 1
Bringing Out the Dead is listed (or ranked) 50 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