Entertainment
848 voters

Movies That Turned 20 in 2019

Updated January 3, 2020 31.9k votes 848 voters 9.8k 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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  • Austin Powers: The Spy Who Shagged Me1
    467
    133

    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
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  • The Boondock Saints2
    484
    213

    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
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  • South Park: Bigger, Longer & Uncut3
    345
    139

    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
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  • Dogma4
    481
    243

    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
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  • The Matrix5
    659
    356

    The Matrix

    Keanu Reeves, Hugo Weaving

    Released1999

    Directed byAndy Wachowski, Lana Wachowski

    The Matrix is a 1999 American-Australian science fiction action film written and directed by...  more
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  • American Beauty6
    388
    194

    American Beauty

    Kevin Spacey, Annette Bening

    Released1999

    Directed bySam Mendes

    American Beauty is a 1999 American drama film directed by Sam Mendes. An advertising executive...  more
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  • The Green Mile7
    618
    340

    The Green Mile

    Tom Hanks, Gary Sinise

    Released1999

    Directed byFrank Darabont

    The Green Mile is a 1999 American fantasy drama film directed by Frank Darabont and adapted...  more
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  • Cruel Intentions8
    233
    117

    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
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  • Three Kings9
    196
    110

    Three Kings

    George Clooney, Mark Wahlberg

    Released1999

    Directed byDavid O. Russell

    Three Kings is a 1999 satirical comedy film written and directed by David O. Russell from a...  more
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  • Varsity Blues10
    400
    270

    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
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  • Star Wars Episode I: The Phantom Menace11
    248
    152

    Star Wars Episode I: The Phantom Menace

    Natalie Portman, Keira Knightley

    Released1999

    Directed byGeorge Lucas

    (32 Years Before Episode IV) Stranded on the desert planet Tatooine after rescuing young Queen...  more
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  • Girl, Interrupted12
    175
    97

    Girl, Interrupted

    Angelina Jolie, Winona Ryder

    Released1999

    Directed byJames Mangold

    Girl, Interrupted is a 1999 American drama film, and an adaptation of Susanna Kaysen's 1993...  more
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  • The Blair Witch Project13
    211
    132

    The Blair Witch Project

    Heather Donahue, Joshua Leonard

    Released1999

    Directed byDaniel Myrick, Eduardo Sánchez

    The Blair Witch Project is a 1999 American found footage horror film written, directed and...  more
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  • Wild Wild West14
    202
    125

    Wild Wild West

    Salma Hayek, Will Smith

    Released1999

    Directed byBarry Sonnenfeld

    Wild Wild West is a 1999 American steampunk western action-comedy film directed by Barry...  more
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  • Analyze This15
    165
    99

    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
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  • Mystery Men16
    150
    89

    Mystery Men

    Ben Stiller, Tom Waits

    Released1999

    Directed byKinka Usher

    Mystery Men is a 1999 American superhero comedy film directed by Kinka Usher and written by...  more
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  • Never Been Kissed17
    164
    106

    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
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  • Galaxy Quest18
    343
    275

    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
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  • The World Is Not Enough19
    130
    85

    The World Is Not Enough

    Pierce Brosnan, Denise Richards

    Released1999

    Directed byMichael Apted

    The World Is Not Enough is the nineteenth spy film in the James Bond series, and the third to...  more
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  • Stigmata20
    137
    98

    Stigmata

    Portia de Rossi, Patricia Arquette

    Released1999

    Directed byRupert Wainwright

    Stigmata is a 1999 supernatural horror film directed by Rupert Wainwright and starring...  more
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  • Man on the Moon21
    152
    113

    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
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  • The Talented Mr. Ripley22
    113
    82

    The Talented Mr. Ripley

    Gwyneth Paltrow, Cate Blanchett

    Released1999

    Directed byAnthony Minghella

    The Talented Mr. Ripley is a 1999 American psychological thriller written for the screen and...  more
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  • Boys Don't Cry23
    106
    78

    Boys Don't Cry

    Hilary Swank, Chloë Sevigny

    Released1999

    Directed byKimberly Peirce

    Boys Don't Cry is a 1999 American independent romantic drama film directed by Kimberly Peirce...  more
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  • Entrapment24
    104
    76

    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
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  • Office Space25
    282
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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
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