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Movies That Turned 20 in 2019

Updated January 3, 2020 22.1k votes 847 voters 9.7k views114 items

List RulesVote 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.

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  • 1
    Office Space is listed (or ranked) 1 on the list Movies That Turned 20 in 2019
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    Office Space

    Jennifer Aniston, John C. McGinley

    Released1999

    Directed byMike Judge

    Office Space is a 1999 American comedy film written and directed by Mike Judge. The film... more on Wikipediaamazon buy button
  • 2
    Toy Story 2 is listed (or ranked) 2 on the list Movies That Turned 20 in 2019
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    115

    Toy Story 2

    Tom Hanks, Kelsey Grammer

    Released1999

    Directed byJohn Lasseter, Lee Unkrich, Ash Brannon

    Toy Story 2 is a 1999 American computer-animated comedy adventure film produced by Pixar... more on Wikipediaamazon buy button
  • 3
    Cruel Intentions is listed (or ranked) 3 on the list Movies That Turned 20 in 2019
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    123

    Cruel Intentions

    Reese Witherspoon, Sarah Michelle Gellar

    Released1999

    Directed byRoger Kumble

    Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe,... more on Wikipediaamazon buy button
  • 4
    Austin Powers: The Spy Who Sha is listed (or ranked) 4 on the list Movies That Turned 20 in 2019
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    138

    Austin Powers: The Spy Who Shagged Me

    Elizabeth Hurley, Heather Graham

    Released1999

    Directed byJay Roach

    Austin Powers: The Spy Who Shagged Me is a 1999 action comedy film and the second film in the... more on Wikipediaamazon buy button
  • 5
    Analyze This is listed (or ranked) 5 on the list Movies That Turned 20 in 2019
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    103

    Analyze This

    Robert De Niro, Billy Crystal

    Released1999

    Directed byHarold Ramis

    Analyze This is a 1999 comedy film directed by Harold Ramis, who co-wrote the screenplay with... more on Wikipediaamazon buy button
  • 6
    Never Been Kissed is listed (or ranked) 6 on the list Movies That Turned 20 in 2019
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    108

    Never Been Kissed

    Jessica Alba, Drew Barrymore

    Released1999

    Directed byRaja Gosnell

    Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew... more on Wikipediaamazon buy button
  • 7
    Varsity Blues is listed (or ranked) 7 on the list Movies That Turned 20 in 2019
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    130

    Varsity Blues

    Ali Larter, Paul Walker

    Released1999

    Directed byBrian Robbins

    Varsity Blues is a 1999 American coming-of-age sports comedy-drama film directed by Brian... more on Wikipediaamazon buy button
  • 8
    Being John Malkovich is listed (or ranked) 8 on the list Movies That Turned 20 in 2019
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    107

    Being John Malkovich

    Cameron Diaz, Brad Pitt

    Released1999

    Directed bySpike Jonze

    Being John Malkovich is a 1999 American fantasy comedy film written by Charlie Kaufman and... more on Wikipediaamazon buy button
  • 9
    Man on the Moon is listed (or ranked) 9 on the list Movies That Turned 20 in 2019
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    118

    Man on the Moon

    Courtney Love, Jim Carrey

    Released1999

    Directed byMiloš Forman

    Man on the Moon is a 1999 American biographical comedy–drama film about the late American... more on Wikipediaamazon buy button
  • 10
    Galaxy Quest is listed (or ranked) 10 on the list Movies That Turned 20 in 2019
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    132

    Galaxy Quest

    Sigourney Weaver, Alan Rickman

    Released1999

    Directed byDean Parisot

    Galaxy Quest is a 1999 American science fiction action comedy film directed by Dean Parisot... more on Wikipediaamazon buy button
  • 11
    Entrapment is listed (or ranked) 11 on the list Movies That Turned 20 in 2019
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    80

    Entrapment

    Catherine Zeta-Jones, Sean Connery

    Released1999

    Directed byJon Amiel

    Entrapment is a 1999 American caper film directed by Jon Amiel and starring Sean Connery and... more on Wikipediaamazon buy button
  • 12
    She's All That is listed (or ranked) 12 on the list Movies That Turned 20 in 2019
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    110

    She's All That

    Sarah Michelle Gellar, Anna Paquin

    Released1999

    Directed byRobert Iscove

    She's All That is a 1999 American teen romantic comedy film directed by Robert Iscove and... more on Wikipediaamazon buy button
  • 13
    Payback is listed (or ranked) 13 on the list Movies That Turned 20 in 2019
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    83

    Payback

    Mel Gibson, Lucy Liu

    Released1999

    Directed byBrian Helgeland

    Payback is a 1999 American action film directed by Brian Helgeland and starring Mel Gibson,... more on Wikipediaamazon buy button
  • 14
    South Park: Bigger, Longer & U is listed (or ranked) 14 on the list Movies That Turned 20 in 2019
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    144

    South Park: Bigger, Longer & Uncut

    George Clooney, Minnie Driver

    Released1999

    Directed byTrey Parker

    South Park: Bigger, Longer & Uncut is a 1999 American adult animated satirical musical comedy... more on Wikipediaamazon buy button
  • 15
    The Boondock Saints is listed (or ranked) 15 on the list Movies That Turned 20 in 2019
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    The Boondock Saints

    Willem Dafoe, Norman Reedus

    Released1999

    Directed byTroy Duffy

    The Boondock Saints is a 1999 American film written and directed by Troy Duffy. The film stars... more on Wikipediaamazon buy button
  • 16
    8mm is listed (or ranked) 16 on the list Movies That Turned 20 in 2019
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    92

    8mm

    Nicolas Cage, Joaquin Phoenix

    Released1999

    Directed byJoel Schumacher

    8mm is a 1999 American-German mystery thriller film directed by Joel Schumacher and written by... more on Wikipediaamazon buy button
  • 17
    Blast from the Past is listed (or ranked) 17 on the list Movies That Turned 20 in 2019
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    99

    Blast from the Past

    Alicia Silverstone, Christopher Walken

    Released1999

    Directed byHugh Wilson

    Blast from the Past is a 1999 American romantic comedy film based on a story and directed by... more on Wikipediaamazon buy button
  • 18
    10 Things I Hate About You is listed (or ranked) 18 on the list Movies That Turned 20 in 2019
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    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

    10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and... more on Wikipediaamazon buy button
  • 19
    The 13th Warrior is listed (or ranked) 19 on the list Movies That Turned 20 in 2019
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    94

    The 13th Warrior

    Omar Sharif, Antonio Banderas

    Released1999

    Directed byJohn McTiernan, Michael Crichton

    The 13th Warrior is a 1999 American historical fiction action film based on the novel and is a... more on Wikipediaamazon buy button
  • 20
    Big Daddy is listed (or ranked) 20 on the list Movies That Turned 20 in 2019
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    215

    Big Daddy

    Adam Sandler, Jon Stewart

    Released1999

    Directed byDennis Dugan

    Big Daddy is a 1999 American comedy film directed by Dennis Dugan and starring Adam Sandler.... more on Wikipediaamazon buy button
  • 21
    The Mummy is listed (or ranked) 21 on the list Movies That Turned 20 in 2019
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    272

    The Mummy

    Rachel Weisz, Brendan Fraser

    Released1999

    Directed byStephen Sommers

    The Mummy is a 1999 American fantasy adventure film written and directed by Stephen Sommers... more on Wikipediaamazon buy button
  • 22
    The Messenger: The Story of Jo is listed (or ranked) 22 on the list Movies That Turned 20 in 2019
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    114

    The Messenger: The Story of Joan of Arc

    Milla Jovovich, Dustin Hoffman

    Released1999

    Directed byLuc Besson

    The Messenger: The Story of Joan of Arc is a 1999 French historical drama film directed by Luc... more on Wikipediaamazon buy button
  • 23
    Tarzan is listed (or ranked) 23 on the list Movies That Turned 20 in 2019
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    104

    Tarzan

    Rosie O'Donnell, Glenn Close

    Released1999

    Directed byKevin Lima, Chris Buck

    Tarzan is a 1999 American animated adventure musical film produced by Walt Disney Feature... more on Wikipediaamazon buy button
  • 24
    Dogma is listed (or ranked) 24 on the list Movies That Turned 20 in 2019
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    Dogma

    Ben Affleck, Matt Damon

    Released1999

    Directed byKevin Smith

    Dogma is a 1999 American comedy film written and directed by Kevin Smith. The existence of... more on Wikipediaamazon buy button
  • 25
    The Iron Giant is listed (or ranked) 25 on the list Movies That Turned 20 in 2019
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    123

    The Iron Giant

    Jennifer Aniston, Vin Diesel

    Released1999

    Directed byBrad Bird

    The Iron Giant is a 1999 American animated science fiction comedy-drama film using both... more on Wikipediaamazon buy button
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