Ranked: Films of 1999
by BenAfweck | created - 16 Dec 2014 | updated - 16 Dec 2014 | Public- Instant Watch Options
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1. 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: 2,322,735 | Gross: $37.03M
2. 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: 1,050,979 | Gross: $293.51M
3. 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: 2,052,298 | Gross: $171.48M
4. 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: 1,406,750 | Gross: $136.80M
5. Dogma (1999)
R | 130 min | Adventure, Comedy, Drama
An abortion clinic worker with a special heritage is called upon to save the existence of humanity from being negated by two renegade angels trying to exploit a loop-hole and reenter Heaven.
Director: Kevin Smith | Stars: Ben Affleck, Matt Damon, Linda Fiorentino, Bud Cort
Votes: 228,603 | Gross: $30.65M
6. Beyond the Mat (1999)
R | 102 min | Documentary, Biography, Sport
A heartfelt documentary focusing on the day-to-day lives of professional wrestlers, some on the rise, some on the wane, and others fighting for their lives.
Director: Barry W. Blaustein | Stars: Terry Funk, Mick Foley, Jake Roberts, Barry W. Blaustein
Votes: 9,472 | Gross: $2.05M
7. 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: 328,387 | Gross: $22.46M
8. Analyze This (1999)
R | 103 min | Comedy, Crime
A comedy about a psychiatrist whose number-one patient is an insecure mob boss.
Director: Harold Ramis | Stars: Robert De Niro, Billy Crystal, Lisa Kudrow, Chazz Palminteri
Votes: 161,648 | Gross: $106.89M
9. The Talented Mr. Ripley (1999)
R | 139 min | Crime, Drama, Thriller
In late 1950s New York, a young underachiever named Tom Ripley is sent to Italy to retrieve Dickie Greenleaf, a rich and spoiled millionaire playboy. But when the errand fails, Ripley takes extreme measures.
Director: Anthony Minghella | Stars: Matt Damon, Gwyneth Paltrow, Jude Law, Cate Blanchett
Votes: 242,239 | Gross: $81.30M
10. 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: 353,290 | Gross: $22.86M
11. South Park: Bigger, Longer & Uncut (1999)
R | 81 min | Animation, Comedy, Fantasy
When Stan Marsh and his friends go see an R-rated movie, they start cursing and their parents think that Canada is to blame.
Director: Trey Parker | Stars: Trey Parker, Matt Stone, Mary Kay Bergman, Isaac Hayes
Votes: 214,915 | Gross: $52.04M
12. Big Daddy (1999)
PG-13 | 93 min | Comedy, Drama
A lazy law school graduate adopts a kid to impress his girlfriend, but everything doesn't go as planned.
Director: Dennis Dugan | Stars: Adam Sandler, Joey Lauren Adams, Jon Stewart, Cole Sprouse
Votes: 234,112 | Gross: $163.48M
13. 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: 1,210,567 | Gross: $130.10M
14. 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: 619,470 | Gross: $245.85M
15. Cruel Intentions (1999)
R | 97 min | Drama, Romance
Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.
Director: Roger Kumble | Stars: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
Votes: 205,107 | Gross: $38.77M
16. The Mummy (1999)
PG-13 | 124 min | Action, Adventure, Fantasy
At an archaeological dig in the ancient city of Hamunaptra, an American serving in the French Foreign Legion accidentally awakens a mummy who begins to wreak havoc as he searches for the reincarnation of his long-lost love.
Director: Stephen Sommers | Stars: Brendan Fraser, Rachel Weisz, John Hannah, Arnold Vosloo
Votes: 460,664 | Gross: $155.25M
17. Austin Powers: The Spy Who Shagged Me (1999)
PG-13 | 95 min | Action, Adventure, Comedy
Dr. Evil is back and has invented a new time machine that allows him to go back to the 1960s and steal Austin Powers' mojo, inadvertently leaving him "shagless".
Director: Jay Roach | Stars: Mike Myers, Heather Graham, Michael York, Robert Wagner
Votes: 248,761 | Gross: $206.04M
18. Office Space (1999)
R | 89 min | Comedy
Three company workers who hate their jobs decide to rebel against their greedy boss.
Director: Mike Judge | Stars: Ron Livingston, Jennifer Aniston, David Herman, Ajay Naidu
Votes: 287,478 | Gross: $10.82M
19. Mickey Blue Eyes (1999)
PG-13 | 102 min | Comedy, Crime, Romance
An English auctioneer proposes to the daughter of a Mafia kingpin, only to realize that certain "favors" would be asked of him.
Directors: Kelly Makin, Carl Gottlieb | Stars: Hugh Grant, Jeanne Tripplehorn, James Caan, Burt Young
Votes: 38,214 | Gross: $33.86M
20. 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: 856,186 | Gross: $474.54M
21. Man on the Moon (1999)
R | 118 min | Biography, Comedy, Drama
The life and career of legendary comedian Andy Kaufman.
Director: Milos Forman | Stars: Jim Carrey, Danny DeVito, Gerry Becker, Greyson Erik Pendry
Votes: 137,455 | Gross: $34.58M
22. Anna and the King (1999)
PG-13 | 148 min | Drama, History, Romance
The story of the romance between the King of Siam and widowed British schoolteacher, Anna Leonowens, during the 1860s.
Director: Andy Tennant | Stars: Jodie Foster, Chow Yun-Fat, Bai Ling, Tom Felton
Votes: 38,976 | Gross: $39.26M
23. Bringing Out the Dead (1999)
R | 121 min | Drama, Thriller
Haunted by the patients he failed to save, a monumentally burned-out Manhattan ambulance paramedic fights to maintain his sanity over three increasingly turbulent nights.
Director: Martin Scorsese | Stars: Nicolas Cage, Patricia Arquette, John Goodman, Ving Rhames
Votes: 76,032 | Gross: $16.64M
24. Three Kings (1999)
R | 114 min | Action, Adventure, Comedy
In the aftermath of the Persian Gulf War, four soldiers set out to steal gold that was stolen from Kuwait, but they discover people who desperately need their help.
Director: David O. Russell | Stars: George Clooney, Mark Wahlberg, Ice Cube, Spike Jonze
Votes: 180,424 | Gross: $60.65M
25. Galaxy Quest (1999)
PG | 102 min | Adventure, Comedy, Sci-Fi
The alumni cast of a space opera television series have to play their roles as the real thing when an alien race needs their help. However, they also have to defend both Earth and the alien race from a reptilian warlord.
Director: Dean Parisot | Stars: Tim Allen, Sigourney Weaver, Alan Rickman, Tony Shalhoub
Votes: 178,093 | Gross: $71.58M
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