1999 - Top 50
by jeanettdrevsfeldt | created - 9 months ago | updated - 8 months ago | Public- Instant Watch Options
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1. 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: 1,671,156 | Gross: $171.48M
2. 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: 526,224 | Gross: $245.85M
3. Notting Hill (1999)
PG-13 | 124 min | Comedy, Drama, Romance
The life of a simple bookshop owner changes when he meets the most famous film star in the world.
Director: Roger Michell | Stars: Hugh Grant, Julia Roberts, Richard McCabe, Rhys Ifans
Votes: 274,615 | Gross: $116.09M
4. 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: 729,612 | Gross: $474.54M
5. The Sixth Sense (1999)
PG-13 | 107 min | Drama, Mystery, Thriller
A boy who communicates with spirits seeks the help of a disheartened child psychologist.
Director: M. Night Shyamalan | Stars: Bruce Willis, Haley Joel Osment, Toni Collette, Olivia Williams
Votes: 909,705 | Gross: $293.51M
6. Love at First Hiccough (1999)
Not Rated | 85 min | Comedy
16 y.o. Danish high school sophomore Viktor falls in love with senior Anja at 1st hiccup. Their little brothers (BFFs) invite him to Anja's 18th birthday party. Viktor's 2 friends also help. Where does Anja's arrogant boyfriend fit in?
Director: Tomas Villum Jensen | Stars: Robert Hansen, Sofie Lassen-Kahlke, Sebastian Jessen, Rasmus Albeck
Votes: 2,543
7. 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: 178,933 | Gross: $38.33M
8. American Pie (1999)
R | 95 min | Comedy
Four teenage boys enter a pact to lose their virginity by prom night.
Directors: Paul Weitz, Chris Weitz | Stars: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Jennifer Coolidge
Votes: 375,428 | Gross: $102.56M
9. Fight Club (1999)
R | 139 min | Drama
An insomniac office worker and a devil-may-care soapmaker form an underground fight club that evolves into something much, much more.
Director: David Fincher | Stars: Brad Pitt, Edward Norton, Meat Loaf, Zach Grenier
Votes: 1,849,005 | Gross: $37.03M
10. 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: 1,067,314 | Gross: $130.10M
11. The One and Only (1999)
106 min | Comedy, Romance
When handyman Niller comes to install Sus' new kitchen one day, their immediate crush is a sweet escape from both of their problematic relationships.
Director: Susanne Bier | Stars: Sidse Babett Knudsen, Niels Olsen, Søs Egelind, Rafael Edholm
Votes: 4,344
12. The Talented Mr. Ripley (1999)
R | 139 min | Crime, Drama, Thriller
In late 1950s New York, Tom Ripley, a young underachiever, 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: 181,754 | Gross: $81.30M
13. The Green Mile (1999)
R | 189 min | Crime, Drama, Fantasy
The lives of guards on Death Row are affected by one of their charges: a black man accused of child murder and rape, yet who has a mysterious gift.
Director: Frank Darabont | Stars: Tom Hanks, Michael Clarke Duncan, David Morse, Bonnie Hunt
Votes: 1,143,682 | Gross: $136.80M
14. 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: 389,268 | Gross: $155.25M
15. 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: 93,074 | Gross: $57.55M
16. Tarzan (1999)
G | 88 min | Animation, Adventure, Family
A man raised by gorillas must decide where he really belongs when he discovers he is a human.
Directors: Chris Buck, Kevin Lima | Stars: Tony Goldwyn, Minnie Driver, Brian Blessed, Glenn Close
Votes: 203,495 | Gross: $171.09M
17. 10 Things I Hate About You (1999)
PG-13 | 97 min | Comedy, Drama, Romance
A pretty, popular teenager can't go out on a date until her ill-tempered older sister does.
Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
Votes: 296,705 | Gross: $38.18M
18. 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: 191,900 | Gross: $52.04M
19. Sleepy Hollow (1999)
R | 105 min | Fantasy, Horror, Mystery
Ichabod Crane is sent to Sleepy Hollow to investigate the decapitations of three people, with the culprit being the legendary apparition, The Headless Horseman.
Director: Tim Burton | Stars: Johnny Depp, Christina Ricci, Miranda Richardson, Michael Gambon
Votes: 331,496 | Gross: $101.07M
20. The Virgin Suicides (1999)
R | 97 min | Drama, Romance
A group of male friends become obsessed with five mysterious sisters who are sheltered by their strict, religious parents in suburban Detroit in the mid 1970s.
Director: Sofia Coppola | Stars: Kirsten Dunst, Josh Hartnett, James Woods, Kathleen Turner
Votes: 143,987 | Gross: $4.86M
21. In China They Eat Dogs (1999)
Not Rated | 91 min | Action, Comedy, Crime
Two brothers, one cold and ruthless, the other sensitive and reluctant, and their brutal misadventures.
Director: Lasse Spang Olsen | Stars: Kim Bodnia, Dejan Cukic, Nikolaj Lie Kaas, Tomas Villum Jensen
Votes: 20,096
22. Big Daddy (1999)
PG-13 | 93 min | Comedy, Drama
A lazy law school grad adopts a kid to impress his girlfriend, but everything doesn't go as planned and he becomes the unlikely foster father.
Director: Dennis Dugan | Stars: Adam Sandler, Joey Lauren Adams, Jon Stewart, Cole Sprouse
Votes: 199,600 | Gross: $163.48M
23. She's All That (1999)
PG-13 | 95 min | Comedy, Romance
A high school jock makes a bet that he can turn an unattractive girl into the school's prom queen.
Director: Robert Iscove | Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker
Votes: 84,372 | Gross: $63.37M
24. The World Is Not Enough (1999)
PG-13 | 128 min | Action, Adventure, Crime
James Bond uncovers a nuclear plot while protecting an oil heiress from her former kidnapper, an international terrorist who can't feel pain.
Director: Michael Apted | Stars: Pierce Brosnan, Sophie Marceau, Robert Carlyle, Denise Richards
Votes: 188,152 | Gross: $126.94M
25. The Bone Collector (1999)
R | 118 min | Crime, Drama, Mystery
A quadriplegic ex-homicide detective and his partner try to track down a serial killer who is terrorizing New York City.
Director: Phillip Noyce | Stars: Denzel Washington, Angelina Jolie, Queen Latifah, Michael Rooker
Votes: 154,325 | Gross: $66.52M
26. The Blair Witch Project (1999)
R | 81 min | Horror, Mystery
Three film students vanish after traveling into a Maryland forest to film a documentary on the local Blair Witch legend, leaving only their footage behind.
Directors: Daniel Myrick, Eduardo Sánchez | Stars: Heather Donahue, Michael C. Williams, Joshua Leonard, Bob Griffin
Votes: 232,137 | Gross: $140.54M
27. 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: 123,916 | Gross: $34.58M
28. Stuart Little (1999)
PG | 84 min | Adventure, Comedy, Family
The Little family adopt a charming young mouse named Stuart, but the family cat wants rid of him.
Director: Rob Minkoff | Stars: Michael J. Fox, Geena Davis, Hugh Laurie, Jonathan Lipnicki
Votes: 125,617 | Gross: $140.04M
29. Wild Wild West (1999)
PG-13 | 106 min | Action, Comedy, Sci-Fi
The two best special agents in the Wild West must save President Grant from the clutches of a diabolical, wheelchair-bound, steampunk-savvy, Confederate scientist bent on revenge for losing the Civil War.
Director: Barry Sonnenfeld | Stars: Will Smith, Kevin Kline, Kenneth Branagh, Salma Hayek
Votes: 152,864 | Gross: $113.81M
30. Never Been Kissed (1999)
PG-13 | 107 min | Comedy, Drama, Romance
A newspaper reporter enrolls in high school as part of research for a story.
Director: Raja Gosnell | Stars: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon
Votes: 83,191 | Gross: $55.47M
31. Eyes Wide Shut (1999)
R | 159 min | Drama, Mystery, Thriller
A New York City doctor embarks on a harrowing, night-long odyssey of sexual and moral discovery after his wife reveals a painful secret to him.
Director: Stanley Kubrick | Stars: Tom Cruise, Nicole Kidman, Todd Field, Sydney Pollack
Votes: 302,353 | Gross: $55.69M
32. 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: 289,054 | Gross: $22.46M
33. Klinkevals (1999)
95 min | Drama
Copenhagen over century ago: a mother sees her sisters getting ahead in life while she's stuck due to her husband's long stays at a mental hospital. At a picnic with her sisters and families, she dances Klinkevals with a handsome stranger.
Director: Hans Kristensen | Stars: Mette Lisby, Pelle Koppel, Lars Simonsen, Bodil Jørgensen
Votes: 245
34. Simply Irresistible (1999)
PG-13 | 96 min | Comedy, Drama, Fantasy
A magical crab works wonders for a terrible chef's culinary skills, leading her towards the man of her dreams.
Director: Mark Tarlov | Stars: Sarah Michelle Gellar, Sean Patrick Flanery, Patricia Clarkson, Dylan Baker
Votes: 13,266 | Gross: $4.39M
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