Best Movies of 1999
by lintonskanshed | created - 20 Apr 2014 | updated - 23 Sep 2017 | Public- Instant Watch Options
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1. Eyes Wide Shut (1999)
R | 159 min | Drama, Mystery, Thriller
A Manhattan doctor embarks on a bizarre, night-long odyssey after his wife's admission of unfulfilled longing.
Director: Stanley Kubrick | Stars: Tom Cruise, Nicole Kidman, Todd Field, Sydney Pollack
Votes: 375,072 | Gross: $55.69M
2. Magnolia (1999)
R | 188 min | Drama
An epic mosaic of interrelated characters in search of love, forgiveness and meaning in the San Fernando Valley.
Director: Paul Thomas Anderson | Stars: Tom Cruise, Jason Robards, Julianne Moore, Philip Seymour Hoffman
Votes: 328,455 | Gross: $22.46M
3. The Green Mile (1999)
R | 189 min | Crime, Drama, Fantasy
A tale set on death row, where gentle giant John Coffey possesses the mysterious power to heal people's ailments. When the lead guard, Paul Edgecombe, recognizes John's gift, he tries to help stave off the condemned man's execution.
Director: Frank Darabont | Stars: Tom Hanks, Michael Clarke Duncan, David Morse, Bonnie Hunt
Votes: 1,407,198 | Gross: $136.80M
4. Fight Club (1999)
R | 139 min | Drama
An insomniac office worker and a devil-may-care soap maker form an underground fight club that evolves into much more.
Director: David Fincher | Stars: Brad Pitt, Edward Norton, Meat Loaf, Zach Grenier
Votes: 2,323,531 | Gross: $37.03M
5. Kikujiro (1999)
PG-13 | 122 min | Drama, Comedy
A young, naive boy sets out alone on the road to find his wayward mother. Soon he finds an unlikely protector in a crotchety man and the two have a series of unexpected adventures along the way.
Director: Takeshi Kitano | Stars: Takeshi Kitano, Yusuke Sekiguchi, Kayoko Kishimoto, The Great Gidayû
Votes: 22,164 | Gross: $0.20M
6. American Beauty (1999)
R | 122 min | Drama
A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend.
Director: Sam Mendes | Stars: Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley
Votes: 1,210,893 | Gross: $130.10M
7. The Straight Story (1999)
G | 112 min | Biography, Drama
An old man makes a long journey by lawnmower to mend his relationship with an ill brother.
Director: David Lynch | Stars: Richard Farnsworth, Sissy Spacek, Jane Galloway Heitz, Joseph A. Carpenter
Votes: 97,455 | Gross: $6.20M
8. The Insider (1999)
R | 157 min | Biography, Drama, Thriller
A research chemist comes under personal and professional attack when he decides to appear in a 60 Minutes exposé on Big Tobacco.
Director: Michael Mann | Stars: Russell Crowe, Al Pacino, Christopher Plummer, Diane Venora
Votes: 180,196 | Gross: $28.97M
9. Ghost Dog: The Way of the Samurai (1999)
R | 116 min | Crime, Drama
An African-American Mafia hit man who models himself after the samurai of old finds himself targeted for death by the mob.
Director: Jim Jarmusch | Stars: Forest Whitaker, Henry Silva, John Tormey, Cliff Gorman
Votes: 96,951 | Gross: $3.31M
10. Beau Travail (1999)
Unrated | 92 min | Drama, War
An ex-Foreign Legion officer recalls his once-glorious life of leading troops in Djibouti.
Director: Claire Denis | Stars: Denis Lavant, Michel Subor, Grégoire Colin, Richard Courcet
Votes: 14,569 | Gross: $0.25M
11. Toy Story 2 (1999)
G | 92 min | Animation, Adventure, Comedy
When Woody is stolen by a toy collector, Buzz and his friends set out on a rescue mission to save Woody before he becomes a museum toy property with his roundup gang Jessie, Prospector, and Bullseye.
Directors: John Lasseter, Ash Brannon, Lee Unkrich | Stars: Tom Hanks, Tim Allen, Joan Cusack, Kelsey Grammer
Votes: 619,585 | Gross: $245.85M
12. The Matrix (1999)
R | 136 min | Action, Sci-Fi
When a beautiful stranger leads computer hacker Neo to a forbidding underworld, he discovers the shocking truth--the life he knows is the elaborate deception of an evil cyber-intelligence.
Directors: Lana Wachowski, Lilly Wachowski | Stars: Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving
Votes: 2,052,856 | Gross: $171.48M
13. Boys Don't Cry (1999)
R | 118 min | Biography, Crime, Drama
A young man named Brandon Teena navigates love, life, and being transgender in rural Nebraska.
Director: Kimberly Peirce | Stars: Hilary Swank, Chloë Sevigny, Peter Sarsgaard, Brendan Sexton III
Votes: 103,285 | Gross: $11.53M
14. The Sixth Sense (1999)
PG-13 | 107 min | Drama, Mystery, Thriller
Malcolm Crowe, a child psychologist, starts treating a young boy, Cole, who encounters dead people and convinces him to help them. In turn, Cole helps Malcolm reconcile with his estranged wife.
Director: M. Night Shyamalan | Stars: Bruce Willis, Haley Joel Osment, Toni Collette, Olivia Williams
Votes: 1,051,236 | Gross: $293.51M
15. Persian Series #2 (1999)
2 min | Short
An experimental short film from the Persian series made by Stan Brakhage.
Director: Stan Brakhage
Votes: 395
16. Being John Malkovich (1999)
R | 113 min | Comedy, Drama, Fantasy
A puppeteer discovers a portal that leads literally into the head of movie star John Malkovich.
Director: Spike Jonze | Stars: John Cusack, Cameron Diaz, Catherine Keener, John Malkovich
Votes: 353,328 | Gross: $22.86M
17. Star Wars: Episode I - The Phantom Menace (1999)
PG | 136 min | Action, Adventure, Fantasy
Two Jedi escape a hostile blockade to find allies and come across a young boy who may bring balance to the Force, but the long dormant Sith resurface to claim their original glory.
Director: George Lucas | Stars: Ewan McGregor, Liam Neeson, Natalie Portman, Jake Lloyd
Votes: 856,362 | Gross: $474.54M
18. American Pimp (1999)
R | 87 min | Documentary
Street pimps, all of them African-American, discuss their lives and work: getting started, being flamboyant, pimping in various U.S. cities, bringing a woman into their group, taking a ... See full summary »
Directors: Albert Hughes, Allen Hughes | Stars: John S. Dickson, Antonio Fargas, Heidi Fleiss, L. Hammond
Votes: 2,369 | Gross: $0.29M
19. Persian Series #3 (1999)
2 min | Short
An experimental short film from the Persian series made by Stan Brakhage.
Director: Stan Brakhage
Votes: 398
20. Girl, Interrupted (1999)
R | 127 min | Biography, Drama
A directionless teenager, Susanna, is rushed to Claymoore, a mental institution, after a supposed suicide attempt. There, she befriends a group of troubled women who deeply influence her life.
Director: James Mangold | Stars: Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy
Votes: 211,290 | Gross: $28.87M
21. Outer Space (1999)
Not Rated | 10 min | Short, Horror
Footage from The Entity (1982) is edited into an abstract nightmare.
Director: Peter Tscherkassky | Star: Barbara Hershey
Votes: 2,805
22. The Cider House Rules (1999)
PG-13 | 126 min | Drama, Romance
A compassionate young man, raised in an orphanage and trained to be a doctor there, decides to leave to see the world.
Director: Lasse Hallström | Stars: Tobey Maguire, Charlize Theron, Michael Caine, Delroy Lindo
Votes: 104,789 | Gross: $57.55M
23. Screwed in Tallinn (1999 TV Movie)
59 min | Comedy, Drama
Percy Nilegaard collects Swedish single men and embarks on a bus trip to Tallinn with a so-called "highly-experienced driver".
Director: Tomas Alfredson | Stars: Robert Gustafsson, Jonas Inde, Johan Rheborg, Tomas Almgren
Votes: 5,643
24. The Dark Tower (1999)
3 min | Short
An experimental short film by Stan Brakhage which displays various lights and colors.
Director: Stan Brakhage
Votes: 713
25. Election Night (1998)
Not Rated | 11 min | Short, Comedy
On his way to the polls, an idealist yet absent-minded voter must endure continuous waves of racist cab drivers and their offensive remarks.
Director: Anders Thomas Jensen | Stars: Ulrich Thomsen, Jens Jørn Spottag, John Martinus, Ole Thestrup
Votes: 2,440
26. Persian Series #1 (1999)
2 min | Short
An experimental short film from the Persian series made by Stan Brakhage.
Director: Stan Brakhage
Votes: 415
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