best movies by year The Best Movies of 1999  

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List Rules Only movies released in theatres 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.
list ordered by

1
141 57
Fight Club is listed (or ranked) 1 on the list The Best Movies of 1999
Fight Club Brad Pitt, Jared Leto, Helena Bonham Carter

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2
124 61
The Matrix is listed (or ranked) 2 on the list The Best Movies of 1999
The Matrix Keanu Reeves, Hugo Weaving, Carrie-Anne Moss

3
120 43
The Sixth Sense is listed (or ranked) 3 on the list The Best Movies of 1999
The Sixth Sense Bruce Willis, Mischa Barton, Haley Joel Osment

4
119 42
American Beauty is listed (or ranked) 4 on the list The Best Movies of 1999
American Beauty Kevin Spacey, Annette Bening, Mena Suvari

5
108 53
The Green Mile is listed (or ranked) 5 on the list The Best Movies of 1999
The Green Mile Tom Hanks, Gary Sinise, Sam Rockwell

6
99 38
Toy Story 2 is listed (or ranked) 6 on the list The Best Movies of 1999
Toy Story 2 Tom Hanks, Kelsey Grammer, Tim Allen

7
64 38
Being John Malkovich is listed (or ranked) 7 on the list The Best Movies of 1999
Being John Malkovich Cameron Diaz, Brad Pitt, Charlie Sheen

8
77 43
Office Space is listed (or ranked) 8 on the list The Best Movies of 1999
Office Space Jennifer Aniston, John C. McGinley, Mike Judge

9
51 32
Magnolia is listed (or ranked) 9 on the list The Best Movies of 1999
wiabux added Magnolia Tom Cruise, Julianne Moore, Philip Seymour Hoffman

10
50 34
The Iron Giant is listed (or ranked) 10 on the list The Best Movies of 1999
The Iron Giant Jennifer Aniston, Vin Diesel, Cloris Leachman

11
60 53
The Talented Mr. Ripley is listed (or ranked) 11 on the list The Best Movies of 1999
The Talented Mr. Ripley Gwyneth Paltrow, Cate Blanchett, Matt Damon

12
60 53
Sleepy Hollow is listed (or ranked) 12 on the list The Best Movies of 1999
Sleepy Hollow Johnny Depp, Christina Ricci, Christopher Walken

13
70 52
Austin Powers: The Spy Who Sha... is listed (or ranked) 13 on the list The Best Movies of 1999
Austin Powers: The Spy Who Shagged Me Elizabeth Hurley, Heather Graham, Will Ferrell

14
76 62
American Pie is listed (or ranked) 14 on the list The Best Movies of 1999
American Pie Alyson Hannigan, Tara Reid, Shannon Elizabeth

15
58 54
Dogma is listed (or ranked) 15 on the list The Best Movies of 1999
Dogma Ben Affleck, Matt Damon, Chris Rock

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16
54 49
Eyes Wide Shut is listed (or ranked) 16 on the list The Best Movies of 1999
Eyes Wide Shut Tom Cruise, Nicole Kidman, Stanley Kubrick

17
59 44
Big Daddy is listed (or ranked) 17 on the list The Best Movies of 1999
Big Daddy Adam Sandler, Jon Stewart, Steve Buscemi

18
64 53
The Mummy is listed (or ranked) 18 on the list The Best Movies of 1999
The Mummy Rachel Weisz, Brendan Fraser, Patricia Velásquez

19
41 37
Three Kings is listed (or ranked) 19 on the list The Best Movies of 1999
Three Kings George Clooney, Mark Wahlberg, Ice Cube

20
57 37
10 Things I Hate About You is listed (or ranked) 20 on the list The Best Movies of 1999
10 Things I Hate About You Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger

21
48 51
Notting Hill is listed (or ranked) 21 on the list The Best Movies of 1999
Notting Hill Julia Roberts, Alec Baldwin, Mischa Barton

22
53 42
South Park: Bigger, Longer & U... is listed (or ranked) 22 on the list The Best Movies of 1999
South Park: Bigger, Longer & Uncut George Clooney, Minnie Driver, Isaac Hayes

23
63 74
Star Wars Episode I: The Phant... is listed (or ranked) 23 on the list The Best Movies of 1999
Star Wars Episode I: The Phantom Menace Natalie Portman, Keira Knightley, Ewan McGregor

24
45 33
Galaxy Quest is listed (or ranked) 24 on the list The Best Movies of 1999
Galaxy Quest Sigourney Weaver, Alan Rickman, Tim Allen

25
39 47
The World Is Not Enough is listed (or ranked) 25 on the list The Best Movies of 1999
The World Is Not Enough Pierce Brosnan, Denise Richards, John Cleese

26
41 32
The Insider is listed (or ranked) 26 on the list The Best Movies of 1999
The Insider Al Pacino, Russell Crowe, Christopher Plummer

27
34 34
Any Given Sunday is listed (or ranked) 27 on the list The Best Movies of 1999
Any Given Sunday Cameron Diaz, Al Pacino, Jamie Foxx

28
36 37
The Boondock Saints is listed (or ranked) 28 on the list The Best Movies of 1999
The Boondock Saints Willem Dafoe, Norman Reedus, Billy Connolly

29
36 36
Stir of Echoes is listed (or ranked) 29 on the list The Best Movies of 1999
Stir of Echoes Jennifer Morrison, Kevin Bacon, Illeana Douglas

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30
37 31
Analyze This is listed (or ranked) 30 on the list The Best Movies of 1999
Analyze This Robert De Niro, Billy Crystal, Lisa Kudrow

31
29 27
Arlington Road is listed (or ranked) 31 on the list The Best Movies of 1999
Arlington Road Jeff Bridges, Tim Robbins, Joan Cusack

32
45 33
Cruel Intentions is listed (or ranked) 32 on the list The Best Movies of 1999
Cruel Intentions Reese Witherspoon, Sarah Michelle Gellar, Tara Reid

33
34 30
Man on the Moon is listed (or ranked) 33 on the list The Best Movies of 1999
Man on the Moon Courtney Love, Jim Carrey, Danny DeVito

34
34 29
The Hurricane is listed (or ranked) 34 on the list The Best Movies of 1999
The Hurricane Denzel Washington, Liev Schreiber, Rod Steiger

35
29 35
The Thomas Crown Affair is listed (or ranked) 35 on the list The Best Movies of 1999
The Thomas Crown Affair Pierce Brosnan, Faye Dunaway, Rene Russo

36
41 32
Tarzan is listed (or ranked) 36 on the list The Best Movies of 1999
Tarzan Rosie O'Donnell, Glenn Close, Minnie Driver

37
32 33
Varsity Blues is listed (or ranked) 37 on the list The Best Movies of 1999
Varsity Blues Ali Larter, Paul Walker, Amy Smart

38
34 32
Boys Don't Cry is listed (or ranked) 38 on the list The Best Movies of 1999
Boys Don't Cry Hilary Swank, Chloë Sevigny, Natalie Zea

39
44 38
Girl, Interrupted is listed (or ranked) 39 on the list The Best Movies of 1999
Girl, Interrupted Angelina Jolie, Winona Ryder, Whoopi Goldberg

40
34 28
Election is listed (or ranked) 40 on the list The Best Movies of 1999
Election Reese Witherspoon, Matthew Broderick, Chris Klein

41
32 26
The Virgin Suicides is listed (or ranked) 41 on the list The Best Movies of 1999
The Virgin Suicides Kirsten Dunst, Kathleen Turner, Danny DeVito

42
33 24
Double Jeopardy is listed (or ranked) 42 on the list The Best Movies of 1999
Double Jeopardy Ashley Judd, Tommy Lee Jones, Bruce Campbell

43
24 29
Go is listed (or ranked) 43 on the list The Best Movies of 1999
Go Katie Holmes, Melissa McCarthy, Timothy Olyphant

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44
23 22
The Cider House Rules is listed (or ranked) 44 on the list The Best Movies of 1999
wiabux added The Cider House Rules Charlize Theron, Michael Caine, Paul Rudd

45
32 34
She's All That is listed (or ranked) 45 on the list The Best Movies of 1999
She's All That Sarah Michelle Gellar, Anna Paquin, Lil' Kim

46
18 14
Fantasia 2000 is listed (or ranked) 46 on the list The Best Movies of 1999
Fantasia 2000 Steve Martin, Bette Midler, James Earl Jones

47
17 26
October Sky is listed (or ranked) 47 on the list The Best Movies of 1999
October Sky Jake Gyllenhaal, Laura Dern, Chris Cooper

48
12 9
The Straight Story is listed (or ranked) 48 on the list The Best Movies of 1999
weik added The Straight Story Sissy Spacek, Harry Dean Stanton, Richard Farnsworth

49
27 24
Payback is listed (or ranked) 49 on the list The Best Movies of 1999
Payback Mel Gibson, Lucy Liu, Maria Bello

50
41 55
The Blair Witch Project is listed (or ranked) 50 on the list The Best Movies of 1999
The Blair Witch Project Heather Donahue, Joshua Leonard, Michael C. Williams