watchworthy presents

Movies That Turned 20 in 2019 

Jason Bancroft
Updated January 3, 2020 15.7k votes 841 voters 9.2k 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 that turned 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 that turned 20 years old in 2019?  

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.

Data-driven recommendations based on voting from over 40 million monthly visits to Ranker. Try the free app
list ordered by
1
Office Space is listed (or ranked) 1 on the list Movies That Turned 20 in 2019
Jennifer Aniston, John C. McGinley, Mike Judge

Released: 1999

Directed by: 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
2
10 Things I Hate About Y... is listed (or ranked) 2 on the list Movies That Turned 20 in 2019
Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger

Released: 1999

Directed by: Gil Junger

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
3
Toy Story 2 is listed (or ranked) 3 on the list Movies That Turned 20 in 2019
Tom Hanks, Kelsey Grammer, Tim Allen

Released: 1999

Directed by: John Lasseter, Lee Unkrich, Ash Brannon

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
4
Cruel Intentions is listed (or ranked) 4 on the list Movies That Turned 20 in 2019
Reese Witherspoon, Sarah Michelle Gellar, Tara Reid

Released: 1999

Directed by: Roger Kumble

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
5
Austin Powers: The Spy W... is listed (or ranked) 5 on the list Movies That Turned 20 in 2019
Elizabeth Hurley, Heather Graham, Will Ferrell

Released: 1999

Directed by: Jay Roach

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
6
Varsity Blues is listed (or ranked) 6 on the list Movies That Turned 20 in 2019
Ali Larter, Paul Walker, Amy Smart

Released: 1999

Directed by: Brian Robbins

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
7
Never Been Kissed is listed (or ranked) 7 on the list Movies That Turned 20 in 2019
Jessica Alba, Drew Barrymore, James Franco

Released: 1999

Directed by: Raja Gosnell

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
8
The Boondock Saints is listed (or ranked) 8 on the list Movies That Turned 20 in 2019
Willem Dafoe, Norman Reedus, Billy Connolly

Released: 1999

Directed by: Troy Duffy

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
9
Fight Club is listed (or ranked) 9 on the list Movies That Turned 20 in 2019
Brad Pitt, Jared Leto, Helena Bonham Carter

Released: 1999

Directed by: David Fincher

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
10
Galaxy Quest is listed (or ranked) 10 on the list Movies That Turned 20 in 2019
Sigourney Weaver, Alan Rickman, Tim Allen

Released: 1999

Directed by: Dean Parisot

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
11
Sleepy Hollow is listed (or ranked) 11 on the list Movies That Turned 20 in 2019
Johnny Depp, Christina Ricci, Christopher Walken

Released: 1999

Directed by: Tim Burton

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
12
The Mummy is listed (or ranked) 12 on the list Movies That Turned 20 in 2019
Rachel Weisz, Brendan Fraser, Patricia Velásquez

Released: 1999

Directed by: Stephen Sommers

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
13
The Matrix is listed (or ranked) 13 on the list Movies That Turned 20 in 2019
Keanu Reeves, Hugo Weaving, Carrie-Anne Moss

Released: 1999

Directed by: Andy Wachowski, Lana Wachowski

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
14
The Sixth Sense is listed (or ranked) 14 on the list Movies That Turned 20 in 2019
Bruce Willis, Mischa Barton, Haley Joel Osment

Released: 1999

Directed by: M. Night Shyamalan

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
15
The Messenger: The Story... is listed (or ranked) 15 on the list Movies That Turned 20 in 2019
Milla Jovovich, Dustin Hoffman, John Malkovich

Released: 1999

Directed by: Luc Besson

The Messenger: The Story of Joan of Arc is a 1999 French historical drama film directed by Luc Besson. The film stars Milla Jovovich, John Malkovich, Faye Dunaway and Dustin Hoffman. The ...more
16
Big Daddy is listed (or ranked) 16 on the list Movies That Turned 20 in 2019
Adam Sandler, Jon Stewart, Steve Buscemi

Released: 1999

Directed by: Dennis Dugan

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
17
The Green Mile is listed (or ranked) 17 on the list Movies That Turned 20 in 2019
Tom Hanks, Gary Sinise, Sam Rockwell

Released: 1999

Directed by: Frank Darabont

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
18
Being John Malkovich is listed (or ranked) 18 on the list Movies That Turned 20 in 2019
Cameron Diaz, Brad Pitt, Charlie Sheen

Released: 1999

Directed by: Spike Jonze

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
19
South Park: Bigger, Long... is listed (or ranked) 19 on the list Movies That Turned 20 in 2019
George Clooney, Minnie Driver, Isaac Hayes

Released: 1999

Directed by: Trey Parker

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
20
Dogma is listed (or ranked) 20 on the list Movies That Turned 20 in 2019
Ben Affleck, Matt Damon, Chris Rock

Released: 1999

Directed by: Kevin Smith

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
She's All That is listed (or ranked) 21 on the list Movies That Turned 20 in 2019
Sarah Michelle Gellar, Anna Paquin, Lil' Kim

Released: 1999

Directed by: Robert Iscove

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
22
American Beauty is listed (or ranked) 22 on the list Movies That Turned 20 in 2019
Kevin Spacey, Annette Bening, Mena Suvari

Released: 1999

Directed by: Sam Mendes

American Beauty is a 1999 American drama film directed by Sam Mendes. An advertising executive (Kevin Spacey) has a midlife crisis when he becomes infatuated with his teenage daughter's best ...more
23
Blast from the Past is listed (or ranked) 23 on the list Movies That Turned 20 in 2019
Alicia Silverstone, Christopher Walken, Brendan Fraser

Released: 1999

Directed by: Hugh Wilson

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
Tarzan is listed (or ranked) 24 on the list Movies That Turned 20 in 2019
Rosie O'Donnell, Glenn Close, Minnie Driver

Released: 1999

Directed by: Kevin Lima, Chris Buck

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
25
The Iron Giant is listed (or ranked) 25 on the list Movies That Turned 20 in 2019
Jennifer Aniston, Vin Diesel, Cloris Leachman

Released: 1999

Directed by: Brad Bird

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