1999
by zachariahstonerock | created - 22 Feb 2012 | updated - 7 months ago | Public- Instant Watch Options
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1. 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: 328,336 | Gross: $22.46M
2. The Iron Giant (1999)
PG | 86 min | Animation, Action, Adventure
A young boy befriends a giant robot from outer space that a paranoid government agent wants to destroy.
Director: Brad Bird | Stars: Eli Marienthal, Harry Connick Jr., Jennifer Aniston, Vin Diesel
Votes: 227,205 | Gross: $23.16M
3. 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: 619,336 | Gross: $245.85M
4. 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: 285,290 | Gross: $140.54M
5. Sweet and Lowdown (1999)
PG-13 | 95 min | Comedy, Drama, Music
In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman.
Director: Woody Allen | Stars: Sean Penn, Samantha Morton, Woody Allen, Ben Duncan
Votes: 36,660 | Gross: $4.20M
6. 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: 137,427 | Gross: $34.58M
7. 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: 287,415 | Gross: $10.82M
8. 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: 1,050,710 | Gross: $293.51M
9. 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: 169,092 | Gross: $4.86M
10. Bowfinger (1999)
PG-13 | 97 min | Comedy
When a desperate movie producer fails to get a major star for his bargain-basement film, he decides to shoot the film secretly around him.
Director: Frank Oz | Stars: Steve Martin, Eddie Murphy, Heather Graham, Christine Baranski
Votes: 73,907 | Gross: $66.38M
11. 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: 180,395 | Gross: $60.65M
12. Election (1999)
R | 103 min | Comedy, Romance
A high school teacher meets his match in an over-achieving student politician.
Director: Alexander Payne | Stars: Matthew Broderick, Reese Witherspoon, Loren Nelson, Chris Klein
Votes: 104,470 | Gross: $14.88M
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: 1,210,362 | Gross: $130.10M
14. 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: 178,024 | Gross: $71.58M
15. 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: 2,051,636 | Gross: $171.48M
16. 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: 2,321,757 | Gross: $37.03M
17. 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: 97,405 | Gross: $6.20M
18. Twin Falls Idaho (1999)
R | 111 min | Drama
Conjoined twins have their relationship tested when a woman takes interest in one of them.
Director: Michael Polish | Stars: Michael Polish, Mark Polish, Michele Hicks, Jon Gries
Votes: 5,249 | Gross: $0.99M
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: 383,749 | Gross: $101.07M
20. 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: 76,014 | Gross: $16.64M
21. All About My Mother (1999)
R | 101 min | Comedy, Drama, Romance
A comedy-drama about a bereaved mother, and overwrought actress, her jealous lover, and a pregnant nun.
Director: Pedro Almodóvar | Stars: Cecilia Roth, Marisa Paredes, Candela Peña, Antonia San Juan
Votes: 102,829 | Gross: $8.26M
22. 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: 228,558 | Gross: $30.65M
23. 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: 342,046 | Gross: $116.09M
24. 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: 161,629 | Gross: $106.89M
25. A Midsummer Night's Dream (1999)
PG-13 | 116 min | Comedy, Fantasy, Romance
Lovers' lives are complicated by city law, feuding faerie royalty, and... love.
Director: Michael Hoffman | Stars: Kevin Kline, Michelle Pfeiffer, Rupert Everett, Stanley Tucci
Votes: 26,956 | Gross: $16.07M
26. The Boondock Saints (1999)
R | 108 min | Action, Crime, Thriller
Two Irish Catholic brothers become vigilantes and wipe out Boston's criminal underworld in the name of God.
Director: Troy Duffy | Stars: Willem Dafoe, Sean Patrick Flanery, Norman Reedus, David Della Rocco
Votes: 250,568 | Gross: $0.03M
27. 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: 248,706 | Gross: $206.04M
28. Titus (1999)
R | 162 min | Drama, History, Thriller
Titus returns victorious from war, only to plant the seeds of future turmoil for himself and his family.
Director: Julie Taymor | Stars: Anthony Hopkins, Jessica Lange, Osheen Jones, Dario D'Ambrosi
Votes: 21,458 | Gross: $1.92M
29. 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: 234,047 | Gross: $163.48M
30. Deep Blue Sea (1999)
R | 105 min | Action, Adventure, Sci-Fi
Searching for a cure to Alzheimer's disease, a group of scientists on an isolated research facility become the prey, as a trio of intelligent sharks fight back.
Director: Renny Harlin | Stars: Thomas Jane, Saffron Burrows, Samuel L. Jackson, Jacqueline McKenzie
Votes: 142,515 | Gross: $73.65M
31. 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: 241,812 | Gross: $81.30M
32. Ever After: A Cinderella Story (1998)
PG-13 | 121 min | Drama, Romance
The Brothers Grimm arrive at the home of a wealthy Grande Dame who speaks of the many legends surrounding the fable of the cinder girl before telling the "true" story of her ancestor.
Director: Andy Tennant | Stars: Drew Barrymore, Anjelica Huston, Dougray Scott, Patrick Godfrey
Votes: 81,684 | Gross: $65.71M
33. 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: 433,531 | Gross: $102.56M
34. 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: 384,833 | Gross: $38.18M
35. 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: 855,984 | Gross: $474.54M
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