1999 - Top 50
by jeanettdrevsfeldt | created - 03 Apr 2020 | updated - 27 Dec 2022 | 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: 2,052,000 | 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: 619,432 | Gross: $245.85M
3. Notting Hill (1999)
PG-13 | 124 min | Comedy, Drama, Romance
A set of circumstances makes Anna Scott, a famous actress, fall in love with William Thacker, owner of a bookstore in Notting Hill. But the paparazzi's fascination with her complicates their bond.
Director: Roger Michell | Stars: Hugh Grant, Julia Roberts, Richard McCabe, Rhys Ifans
Votes: 342,099 | 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: 856,099 | Gross: $474.54M
5. 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: 1,050,867 | Gross: $293.51M
6. Kærlighed ved første hik (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: 2,916
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: 205,085 | Gross: $38.77M
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: 433,592 | Gross: $102.56M
9. 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: 2,322,336 | 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: 1,210,477 | 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: 5,152
12. 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: 242,081 | Gross: $81.30M
13. 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: 1,406,534 | 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: 460,576 | 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: 104,771 | Gross: $57.55M
16. Tarzan (1999)
G | 88 min | Animation, Adventure, Comedy
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: 247,075 | Gross: $171.09M
17. 10 Things I Hate About You (1999)
PG-13 | 97 min | Comedy, Drama, Romance
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.
Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
Votes: 384,918 | 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: 214,906 | 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; the culprit is legendary apparition The Headless Horseman.
Director: Tim Burton | Stars: Johnny Depp, Christina Ricci, Miranda Richardson, Michael Gambon
Votes: 383,786 | 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: 169,113 | 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: 23,033
22. 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: 234,085 | 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: 103,771 | Gross: $63.37M
24. The World Is Not Enough (1999)
PG-13 | 128 min | Action, Adventure, Thriller
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: 209,936 | 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: 184,872 | 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: 285,358 | 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: 137,441 | 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: 148,915 | 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: 167,254 | 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: 97,528 | Gross: $55.47M
31. 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: 374,918 | 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: 328,370 | 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: 286
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: 14,921 | Gross: $4.39M
35. Mansfield Park (1999)
PG-13 | 112 min | Comedy, Drama, Romance
Fanny, born into a poor family, is sent away to live with wealthy uncle Sir Thomas, his wife and their four children, where she'll be brought up for a proper introduction to society.
Director: Patricia Rozema | Stars: Frances O'Connor, Jonny Lee Miller, Alessandro Nivola, Hannah Taylor Gordon
Votes: 25,834 | Gross: $4.76M
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