1999 Movies
by kadis_gio | created - 21 Feb 2014 | updated - 20 Aug 2019 | Public- Instant Watch Options
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1. 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: 1,210,814 | Gross: $130.10M
2. 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: 2,323,327 | Gross: $37.03M
3. 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: 1,051,144 | Gross: $293.51M
Seen it.
4. 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: 328,421 | Gross: $22.46M
5. 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: 353,309 | Gross: $22.86M
6. 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: 1,407,060 | Gross: $136.80M
Seen it.
7. 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: 433,713 | Gross: $102.56M
Seen it.
8. 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: 285,457 | Gross: $140.54M
9. 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: 342,198 | Gross: $116.09M
10. 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: 383,852 | Gross: $101.07M
11. 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: 460,805 | Gross: $155.25M
12. 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: 180,176 | Gross: $28.97M
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: 103,280 | Gross: $11.53M
14. 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: 385,119 | Gross: $38.18M
15. 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: 375,033 | Gross: $55.69M
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: 247,155 | Gross: $171.09M
17. 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: 227,381 | Gross: $23.16M
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: 287,517 | Gross: $10.82M
19. 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: 242,518 | Gross: $81.30M
20. 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: 250,639 | Gross: $0.03M
21. 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: 248,794 | Gross: $206.04M
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: 234,160 | Gross: $163.48M
23. 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: 169,165 | Gross: $4.86M
24. 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: 211,269 | Gross: $28.87M
25. 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: 205,128 | Gross: $38.77M
26. 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: 619,547 | Gross: $245.85M
27. 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: 228,624 | Gross: $30.65M
28. Flawless (1999)
R | 112 min | Crime, Drama
An ultraconservative security guard suffers a debilitating stroke and is assigned to a rehabilitative program that includes singing lessons with the drag queen next door.
Director: Joel Schumacher | Stars: Robert De Niro, Philip Seymour Hoffman, Barry Miller, Chris Bauer
Votes: 20,002 | Gross: $4.49M
29. The Best Man (1999)
R | 120 min | Comedy, Drama, Romance
Just before his best friend's wedding, the life of a Chicago writer becomes crazy when his best friend guesses that his new book's story is based on his bride's fervent past.
Director: Malcolm D. Lee | Stars: Taye Diggs, Nia Long, Morris Chestnut, Harold Perrineau
Votes: 11,839 | Gross: $34.10M
30. The Haunting (1999)
PG-13 | 113 min | Fantasy, Horror, Mystery
Dr Marrow enlists Theo, Luke and Nell for a study of sleep disorders at the Hill House. As soon as the terrifying truth about the mansion is revealed, everyone is found fighting for their lives.
Director: Jan de Bont | Stars: Liam Neeson, Catherine Zeta-Jones, Owen Wilson, Lili Taylor
Votes: 80,479 | Gross: $91.41M
31. 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: 209,954 | Gross: $126.94M
32. The 13th Warrior (1999)
R | 102 min | Action, Adventure, History
A man, having fallen in love with the wrong woman, is sent by the sultan himself on a diplomatic mission to a distant land as an ambassador. Stopping at a Viking village port to restock on supplies, he finds himself unwittingly embroiled in a quest to banish a mysterious threat in a distant Viking land.
Directors: John McTiernan, Michael Crichton | Stars: Antonio Banderas, Diane Venora, Dennis Storhøi, Vladimir Kulich
Votes: 132,082 | Gross: $32.70M
33. The Ninth Gate (1999)
R | 133 min | Mystery, Thriller
A book broker discovers his latest find may summon Satan.
Director: Roman Polanski | Stars: Johnny Depp, Frank Langella, Lena Olin, Emmanuelle Seigner
Votes: 197,449 | Gross: $18.66M
34. 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: 180,438 | Gross: $60.65M
35. 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: 104,513 | Gross: $14.88M
36. 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: 104,785 | Gross: $57.55M
37. Go (1999)
R | 102 min | Comedy, Crime
The aftermath of a drug deal as told from three different points of view.
Director: Doug Liman | Stars: Sarah Polley, Jay Mohr, Scott Wolf, Taye Diggs
Votes: 75,148 | Gross: $16.84M
38. Any Given Sunday (1999)
R | 162 min | Drama, Sport
A behind-the-scenes look at the life-and-death struggles of modern-day gladiators and those who lead them.
Director: Oliver Stone | Stars: Al Pacino, Dennis Quaid, Cameron Diaz, James Woods
Votes: 125,886 | Gross: $75.53M
39. Drop Dead Gorgeous (1999)
PG-13 | 97 min | Comedy, Romance, Thriller
A small-town beauty pageant turns deadly as it becomes clear that someone will go to any lengths to win.
Director: Michael Patrick Jann | Stars: Kirsten Dunst, Denise Richards, Ellen Barkin, Allison Janney
Votes: 40,795 | Gross: $10.56M
40. 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: 25,843 | Gross: $4.76M
41. Blast from the Past (1999)
PG-13 | 112 min | Comedy, Drama, Romance
A naive man comes out into the world after spending 35 years in a nuclear fallout shelter.
Director: Hugh Wilson | Stars: Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek
Votes: 71,711 | Gross: $26.49M
42. Cosy Dens (1999)
115 min | Comedy, Drama
Two families, Sebkovi and Krausovi, are celebrating Christmas, but not everyone is in a good mood. Teenage kids think their fathers are totally stupid; fathers are sure their children are nothing more than rebels, hating anything they say.
Director: Jan Hrebejk | Stars: Michael Beran, Miroslav Donutil, Simona Stasová, Kristýna Nováková
Votes: 6,169
43. Between Your Legs (1999)
115 min | Drama, Mystery, Romance
Javier's life gets complicated when a something unexpected turns up in his car's trunk.
Director: Manuel Gómez Pereira | Stars: Victoria Abril, Javier Bardem, Carmelo Gómez, Juan Diego
Votes: 3,068
44. The Glass Agency (1998)
114 min | Action, Drama, Romance
The Glass Agency is the story of a war veteran living in post war Iran. It depicts veterans who are suffering from social problems after the war. Society does not understand them and the ... See full summary »
Director: Ebrahim Hatamikia | Stars: Parviz Parastui, Reza Kianian, Habib Rezaei, Ghasem Zare
Votes: 7,264
45. 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: 97,443 | Gross: $6.20M
46. The Debt Collector (1999)
109 min | Action, Crime, Thriller
Mean, gritty, dirty, and low - and that's just Policeman Gary Keltie (Ken Stott) out for retribution for the horrendous crimes against the helpless people of Edinburgh, Scotland during the ... See full summary »
Director: Anthony Neilson | Stars: Billy Connolly, Ken Stott, Francesca Annis, Iain Robertson
Votes: 1,197
47. Peppermint Candy (1999)
Not Rated | 129 min | Drama
Following a man's suicide, time traverses back to reveal six chapters of his life on why he committed suicide.
Director: Lee Chang-dong | Stars: Sol Kyung-gu, Kim Yeo-jin, Moon So-ri, Se-beom Park
Votes: 10,820
48. 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: 102,855 | Gross: $8.26M
49. eXistenZ (1999)
R | 97 min | Horror, Mystery, Sci-Fi
A game designer on the run from assassins must play her latest virtual reality creation with a marketing trainee to determine if the game has been damaged.
Director: David Cronenberg | Stars: Jude Law, Jennifer Jason Leigh, Ian Holm, Willem Dafoe
Votes: 107,187 | Gross: $2.84M
50. Free Solo (2018)
PG-13 | 100 min | Documentary, Adventure, Sport
Alex Honnold faces the biggest challenge of his career, climbing El Capitan in Yosemite National Park. He pursues it Free Solo, which means climbing without a rope and alone.
Directors: Jimmy Chin, Elizabeth Chai Vasarhelyi | Stars: Alex Honnold, Tommy Caldwell, Jimmy Chin, Cheyne Lempe
Votes: 77,346 | Gross: $17.54M
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