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The 20 Best Movies of 1999 That Will Make You Nostalgic

These films turn 25 this year

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Warner Bros.

What was it about the year 1999 that made it so amazing? Was it Prince foreshadowing all the way back in 1982 that it was going to be an amazing party year? Was it because everybody thought the world was going to end at the strike of midnight on New Years Eve? Was it because TLC released "No Scrubs?" There's lot of reasons why 1999 was so great from an entertainment standpoint, and among those reasons was the emergence of many talented actors being in the early phases of their careers, along with many notable films being released that have in turn withstood the test of time. It honor of the quarter-century mark since the release of these films, we've rounded up the best movies of 1999 that will make you quite nostalgic.

From The Matrix (which stars our guy Keanu Reaves) to 10 Things I Hate About You, these movies defined the year 1999, and encapsulate what the late 1990s were all about (especially if you are a millennial). What exactly was it about '99 that made it an elite year for film? Let's reference a May 2019 New York Times article written by David Friend that in turn references an April 2019 novel penned by Brian Raftery entitled: Best. Movie. Year. Ever.: How 1999 Blew Up the Big Screen. In the review Friend states: "Now comes the culture critic Brian Raftery with "Best. Movie. Year. Ever.: How 1999 Blew Up the Big Screen." He focuses on a bumper crop of breakthrough, subversive, auteur-driven movies — virtually all of which were released theatrically in 1999 — quoting the actor Edward Norton (of 1999’s “Fight Club”), who is hard pressed to name any other 12-month span “that had more really original young filmmakers tapping into the zeitgeist."

Friend continues: "He (Raftery) weaves together film history and cheeky anecdotes from Hollywood insiders, recounting a midnight rave here, a nude ski run there. His tone, like the period’s, is jaunty but jaundiced." We'll leave you to check out the rest of Friend's review (and Raftery's book), on your own accord as both our very interesting. For now, however, lets revisit these wonderful films in honor of the 25-year landmark.

RELATED: The 40 Best Movies of the 2000s

1. The Blair Witch Project (1999)

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2. Fight Club (1999)

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3. The Matrix (1999)

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4. 10 Things I Hate About You (1999)

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5. Magnolia (1999)

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6. Deep Blue Sea (1999)

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7. Star Wars: Episode I – The Phantom Menace (1999)

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8. She's All That (1999)

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9. Cruel Intentions (1999)

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10. South Park: Bigger, Longer & Uncut (1999)

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11. Passport to Paris (1999)

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12. The Bone Collector (1999)

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13. Election (1999)

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14. The Sixth Sense (1999)

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15. Jawbreaker (1999)

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16. The Best Man (1999)

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17. American Pie (1999)

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18. Galaxy Quest (1999)

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19. Notting Hill (1999)

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20. Dick (1999)

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