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The Best Movies of 1999

Updated September 4, 2020 22.5k votes 1.6k voters 39.6k views124 items

List RulesOnly movies released in theaters in 1999.

A list of the best movies of 1999, from blockbusters like The Matrix to cult classics like The Boondock Saints. The '90s were a decade where Hollywood thrived. In were new stars and big blockbusters and 1999 was no exception. Some the best movies of this year are some of the best teen, coming of age, adventure, comedies and dramas in history. The films on here are very memorable and had audiences on the edges of their seats, and still pack a punch so many years after they were first released. You shouldn't be too surprised by the movies listed on here.

As stated before, some of the best movies of the decade were released in 1999. Who could forget The Sixth Sense with Bruce Willis and Haley Joel Osment, Being John Malkovich with John Cusack, Cameron Diaz and Catherine Keener, and of course, South Park: Bigger, Longer & Uncut. And let's not forget about Girl, Interrupted with Angelina Jolie.

The best movies of 1999 featured some of the biggest stars in the movie business. Whether it was the aforementioned stars continuing their success or the breakout performances featured in American Pie, or established stars like Brad Pitt and Edward Norton in Fight Club.

Some of the best movies of all time were released in 1999. This is the ultimate list of the best movies of 1999, which shouldn't feature the best movies of 1998. Vote and re-rank this list according to how you think the best movies of that year should be reflected. If you notice that there's a movie from this year that should be on this list but is missing, feel free to add it.
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  • 26
    Double Jeopardy is listed (or ranked) 26 on the list The Best Movies of 1999
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    Double Jeopardy

    Ashley Judd, Tommy Lee Jones

    Released1999

    Directed byBruce Beresford

    Double Jeopardy is a 1999 American mystery-thriller film directed by Bruce Beresford and... more on Wikipediaamazon buy button
  • 27
    The Talented Mr. Ripley is listed (or ranked) 27 on the list The Best Movies of 1999
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    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 on Wikipediaamazon buy button

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  • 28
    The Insider is listed (or ranked) 28 on the list The Best Movies of 1999
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    The Insider

    Al Pacino, Russell Crowe

    Released1999

    Directed byMichael Mann

    The Insider is a 1999 American drama film directed by Michael Mann, based on the true story of... more on Wikipediaamazon buy button

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  • 29
    The Messenger: The Story of Jo is listed (or ranked) 29 on the list The Best Movies of 1999
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    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

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  • 30
    Boys Don't Cry is listed (or ranked) 30 on the list The Best Movies of 1999
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    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 on Wikipediaamazon buy button

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  • 31
    October Sky is listed (or ranked) 31 on the list The Best Movies of 1999
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    October Sky

    Jake Gyllenhaal, Laura Dern

    Released1999

    Directed byJoe Johnston

    October Sky is a 1999 American biographical film directed by Joe Johnston, starring Jake... more on Wikipediaamazon buy button

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  • 32
    Big Daddy is listed (or ranked) 32 on the list The Best Movies of 1999
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    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
  • 33
    Man on the Moon is listed (or ranked) 33 on the list The Best Movies of 1999
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    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

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  • 34
    Payback is listed (or ranked) 34 on the list The Best Movies of 1999
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    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
  • 35
    The Hurricane is listed (or ranked) 35 on the list The Best Movies of 1999
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    The Hurricane

    Denzel Washington, Liev Schreiber

    Released1999

    Directed byNorman Jewison

    The Hurricane is a 1999 biographical film directed by Norman Jewison, and starring Denzel... more on Wikipediaamazon buy button

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  • 36
    Varsity Blues is listed (or ranked) 36 on the list The Best Movies of 1999
    109
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    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
  • 37
    American Pie is listed (or ranked) 37 on the list The Best Movies of 1999
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    American Pie

    Alyson Hannigan, Tara Reid

    Released1999

    Directed byChris Weitz, Paul Weitz

    American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and... more on Wikipediaamazon buy button

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  • 38
    The Bone Collector is listed (or ranked) 38 on the list The Best Movies of 1999
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    The Bone Collector

    Angelina Jolie, Denzel Washington

    Released1999

    Directed byPhillip Noyce

    The Bone Collector is a 1999 psychological thriller film starring Denzel Washington and... more on Wikipediaamazon buy button

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  • 39
    Go is listed (or ranked) 39 on the list The Best Movies of 1999
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    Go

    Katie Holmes, Melissa McCarthy

    Released1999

    Directed byDoug Liman

    Go is a 1999 comedy film written by John August and directed by Doug Liman, with three... more on Wikipediaamazon buy button

    More Go 

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  • 40
    Blast from the Past is listed (or ranked) 40 on the list The Best Movies of 1999
    86
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    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

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  • 41
    Tarzan is listed (or ranked) 41 on the list The Best Movies of 1999
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    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

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  • 42
    The Astronaut's Wife is listed (or ranked) 42 on the list The Best Movies of 1999
    48
    12

    The Astronaut's Wife

    Charlize Theron, Johnny Depp

    Released1999

    Directed byRand Ravich

    The Astronaut's Wife is a 1999 American science fiction/thriller film directed and written by... more on Wikipediaamazon buy button
  • 43
    Any Given Sunday is listed (or ranked) 43 on the list The Best Movies of 1999
    108
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    Any Given Sunday

    Cameron Diaz, Al Pacino

    Released1999

    Directed byOliver Stone

    Any Given Sunday is a 1999 American drama film directed by Oliver Stone depicting a fictional... more on Wikipediaamazon buy button

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  • 44
    Analyze This is listed (or ranked) 44 on the list The Best Movies of 1999
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    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
  • 45
    The Virgin Suicides is listed (or ranked) 45 on the list The Best Movies of 1999
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    The Virgin Suicides

    Kirsten Dunst, Kathleen Turner

    Released1999

    Directed bySofia Coppola

    The film is a 1999 American drama written and directed by Sofia Coppola, produced by her... more on Wikipediaamazon buy button
  • 46
    The Cider House Rules is listed (or ranked) 46 on the list The Best Movies of 1999
    78
    76

    The Cider House Rules

    Charlize Theron, Michael Caine

    Released1999

    Directed byLasse Hallström

    The Cider House Rules is a 1999 American drama film directed by Lasse Hallström, based on John... more on Wikipediaamazon buy button

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  • 47
    She's All That is listed (or ranked) 47 on the list The Best Movies of 1999
    104
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    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

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  • 48
    Message in a Bottle is listed (or ranked) 48 on the list The Best Movies of 1999
    28
    12

    Message in a Bottle

    Hayden Panettiere, Kevin Costner

    Released1999

    Directed byLuis Mandoki

    Message in a Bottle is a 1999 American romantic drama film directed by Luis Mandoki. Based on... more on Wikipediaamazon buy button

    More 

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  • 49
    The Straight Story is listed (or ranked) 49 on the list The Best Movies of 1999
    61
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    The Straight Story

    Sissy Spacek, Harry Dean Stanton

    Released1999

    Directed byDavid Lynch

    The Straight Story is a 1999 biographical drama film directed by David Lynch. The film was... more on Wikipediaamazon buy button

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  • 50
    Mystery Men is listed (or ranked) 50 on the list The Best Movies of 1999
    70
    69

    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 on Wikipediaamazon buy button

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