Class of 1999
by Floki_Thorfinn | created - 23 Jan 2022 | updated - 1 week ago | Public- Instant Watch Options
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1. 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: 132,171 | Gross: $32.70M
2. Idle Hands (1999)
R | 92 min | Comedy, Fantasy, Horror
A teenage slacker's right hand becomes possessed with murderous intent.
Director: Rodman Flender | Stars: Devon Sawa, Seth Green, Elden Henson, Jessica Alba
Votes: 46,777 | Gross: $4.00M
3. Jawbreaker (1999)
R | 86 min | Comedy, Crime, Thriller
Three of the most popular girls at Reagan High accidentally kill the prom queen with a jawbreaker when a kidnapping goes horribly wrong.
Director: Darren Stein | Stars: Rose McGowan, Rebecca Gayheart, Julie Benz, Alexandra Adi
Votes: 28,962 | Gross: $3.07M
4. 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: 104,581 | Gross: $14.88M
5. Dick (1999)
PG-13 | 94 min | Comedy
After wandering off during a White House tour, two high school girls inadvertently become Richard Nixon's top secret advisers at the height of the Watergate scandal.
Director: Andrew Fleming | Stars: Kirsten Dunst, Michelle Williams, Dan Hedaya, Will Ferrell
Votes: 21,372 | Gross: $6.24M
6. 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: 197,592 | Gross: $18.66M
7. Crazy in Alabama (1999)
PG-13 | 111 min | Comedy, Crime, Drama
An abused wife heads to California to become a movie star while her nephew back in Alabama has to deal with a racially-motivated murder involving a corrupt sheriff.
Director: Antonio Banderas | Stars: Melanie Griffith, David Morse, Lucas Black, Cathy Moriarty
Votes: 7,394 | Gross: $1.95M
8. 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: 40,844 | Gross: $10.56M
9. 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: 385,683 | Gross: $38.18M
10. 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: 169,332 | Gross: $4.86M
11. 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: 1,211,518 | Gross: $130.10M
12. 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: 2,325,833 | Gross: $37.03M
13. 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: 857,305 | Gross: $474.54M
14. 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: 205,271 | Gross: $38.77M
15. 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: 210,031 | Gross: $126.94M
16. 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: 107,257 | Gross: $2.84M
17. Ghost Dog: The Way of the Samurai (1999)
R | 116 min | Crime, Drama
An African-American Mafia hit man who models himself after the samurai of old finds himself targeted for death by the mob.
Director: Jim Jarmusch | Stars: Forest Whitaker, Henry Silva, John Tormey, Cliff Gorman
Votes: 97,006 | Gross: $3.31M
18. 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: 620,068 | Gross: $245.85M
19. 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: 285,781 | Gross: $140.54M
20. 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: 434,005 | Gross: $102.56M
21. 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: 328,651 | Gross: $22.46M
22. 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: 1,408,495 | Gross: $136.80M
23. 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: 2,054,745 | Gross: $171.48M
24. Inspector Gadget (1999)
PG | 78 min | Action, Adventure, Comedy
A security guard's dreams come true when he is selected to be transformed into a cybernetic police officer.
Director: David Kellogg | Stars: Matthew Broderick, Rupert Everett, Joely Fisher, Michelle Trachtenberg
Votes: 50,886 | Gross: $97.40M
25. 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: 180,302 | Gross: $28.97M
26. 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: 248,948 | Gross: $206.04M
27. 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: 215,043 | Gross: $52.04M
28. 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: 287,747 | Gross: $10.82M
29. 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: 461,463 | Gross: $155.25M
30. 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: 97,537 | Gross: $6.20M
31. 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: 353,473 | Gross: $22.86M
32. 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: 375,401 | Gross: $55.69M
33. 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: 149,112 | Gross: $140.04M
34. 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: 243,711 | Gross: $81.30M
35. 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: 137,535 | Gross: $34.58M
36. 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: 234,327 | Gross: $163.48M
37. Entrapment (1999)
PG-13 | 113 min | Action, Crime, Romance
An insurance agent is sent by her employer to track down and help capture an art thief.
Director: Jon Amiel | Stars: Sean Connery, Catherine Zeta-Jones, Ving Rhames, Will Patton
Votes: 123,955 | Gross: $87.70M
38. 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: 384,076 | Gross: $101.07M
39. Bicentennial Man (1999)
PG | 132 min | Drama, Romance, Sci-Fi
An android endeavors to become human as he gradually acquires emotions.
Director: Chris Columbus | Stars: Robin Williams, Embeth Davidtz, Sam Neill, Oliver Platt
Votes: 124,742 | Gross: $58.22M
40. 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: 1,051,950 | Gross: $293.51M
41. 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: 161,740 | Gross: $106.89M
42. 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: 342,498 | Gross: $116.09M
43. 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: 103,877 | Gross: $63.37M
44. Drive Me Crazy (1999)
PG-13 | 91 min | Comedy, Drama, Romance
Nicole and Chase used to be BFFs, then junior high happened. The high school centennial dance is coming but Nicole gets dumped. So does Chase. They stage a relationship to get at their exes. They visit each other's worlds. Love in the air?
Director: John Schultz | Stars: Melissa Joan Hart, Adrian Grenier, Stephen Collins, Mark Metcalf
Votes: 21,304 | Gross: $17.85M
45. 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: 227,668 | Gross: $23.16M
46. 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: 180,531 | Gross: $60.65M
47. The Astronaut's Wife (1999)
R | 109 min | Drama, Sci-Fi, Thriller
After an explosion in space and subsequent two-minute radio-out period, two astronauts return home to their wives. Slightly it's revealed that they're not the same as they were.
Director: Rand Ravich | Stars: Charlize Theron, Johnny Depp, Joe Morton, Clea DuVall
Votes: 57,455 | Gross: $10.67M
48. The General's Daughter (1999)
R | 116 min | Crime, Drama, Mystery
When the daughter of a well-known and well-respected base commander is murdered, an undercover detective is summoned to look into the matter and finds a slew of cover-ups at West Point.
Director: Simon West | Stars: John Travolta, Madeleine Stowe, James Cromwell, Timothy Hutton
Votes: 63,869 | Gross: $102.71M
49. 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: 97,609 | Gross: $55.47M
50. 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: 167,335 | Gross: $113.81M
51. 8MM (1999)
R | 123 min | Crime, Drama, Mystery
A private investigator is hired to discover if a "snuff film" is authentic or not.
Director: Joel Schumacher | Stars: Nicolas Cage, Joaquin Phoenix, James Gandolfini, Peter Stormare
Votes: 142,791 | Gross: $36.66M
52. Deuce Bigalow: Male Gigolo (1999)
R | 88 min | Comedy, Romance
An average aquarium cleaner house-sits for a gigolo, only to be forced to become one himself.
Director: Mike Mitchell | Stars: Rob Schneider, William Forsythe, Eddie Griffin, Arija Bareikis
Votes: 80,008 | Gross: $65.54M
53. The Messenger: The Story of Joan of Arc (1999)
R | 148 min | Adventure, Biography, Drama
A young girl receives a vision that drives her to rid France of its oppressors.
Director: Luc Besson | Stars: Milla Jovovich, John Malkovich, Rab Affleck, Stéphane Algoud
Votes: 69,726 | Gross: $14.28M
54. Summer of Sam (1999)
R | 142 min | Crime, Drama, Romance
Spike Lee's take on the "Son of Sam" murders in New York City during the summer of 1977 centering on the residents of an Italian-American Northeast Bronx neighborhood who live in fear and distrust of one another.
Director: Spike Lee | Stars: John Leguizamo, Adrien Brody, Mira Sorvino, Jennifer Esposito
Votes: 41,342 | Gross: $19.28M
55. 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: 104,848 | Gross: $57.55M
56. 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: 36,698 | Gross: $4.20M
57. Virus (1999)
R | 99 min | Action, Horror, Sci-Fi
After outrunning a typhoon at sea, a strong-willed tugboat navigator and her crew discover a high-tech alien life form that's taken control of a Russian research vessel and aims to destroy on a massive scale.
Director: John Bruno | Stars: Jamie Lee Curtis, Donald Sutherland, William Baldwin, Joanna Pacula
Votes: 29,936 | Gross: $14.01M
58. Stigmata (1999)
R | 103 min | Horror, Mystery
When a young woman becomes afflicted by stigmata, a priest is sent to investigate her case, which may have severe ramifications for his faith and for the Catholic Church itself.
Director: Rupert Wainwright | Stars: Patricia Arquette, Gabriel Byrne, Jonathan Pryce, Nia Long
Votes: 72,291 | Gross: $50.05M
59. Ride with the Devil (I) (1999)
R | 138 min | Drama, Romance, War
During the American Civil War, two friends join the Bushwhackers, a militant group loyal to the Confederacy.
Director: Ang Lee | Stars: Tobey Maguire, Skeet Ulrich, Jewel, Jeremy W. Auman
Votes: 14,562 | Gross: $0.63M
60. Edtv (1999)
PG-13 | 122 min | Comedy, Drama
A video store clerk agrees to have his life filmed by a camera crew for a television show.
Director: Ron Howard | Stars: Matthew McConaughey, Jenna Elfman, Geoffrey Blake, Gail Boggs
Votes: 45,045 | Gross: $22.36M
61. Life (I) (1999)
R | 108 min | Comedy, Crime, Drama
In 1932, two strangers are wrongfully convicted and develop a strong friendship in prison that lasts them through the 20th century.
Director: Ted Demme | Stars: Eddie Murphy, Martin Lawrence, Obba Babatundé, Nick Cassavetes
Votes: 54,807 | Gross: $63.84M
62. 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: 211,487 | Gross: $28.87M
63. 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: 125,921 | Gross: $75.53M
64. 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: 247,412 | Gross: $171.09M
65. 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: 76,092 | Gross: $16.64M
66. Muppets from Space (1999)
G | 87 min | Adventure, Comedy, Family
Gonzo is contacted by his alien family through his breakfast cereal. But when the men in black kidnap him, it's up to Kermit and the gang to rescue Gonzo and help him reunite with his long-lost family.
Director: Tim Hill | Stars: Dave Goelz, Steve Whitmire, Bill Barretta, Jerry Nelson
Votes: 20,628 | Gross: $16.63M
67. Wing Commander (1999)
PG-13 | 100 min | Action, Adventure, Sci-Fi
Blair, a fighter pilot, joins an interstellar war to fight the evil Kilrathi who are trying to destroy the universe.
Director: Chris Roberts | Stars: Freddie Prinze Jr., Matthew Lillard, Saffron Burrows, Tchéky Karyo
Votes: 17,420 | Gross: $11.58M
68. The Hurricane (1999)
R | 146 min | Biography, Drama, Sport
The story of Rubin 'Hurricane' Carter, a boxer wrongly imprisoned for murder, and the people who aided in his fight to prove his innocence.
Director: Norman Jewison | Stars: Denzel Washington, Vicellous Shannon, Deborah Kara Unger, Liev Schreiber
Votes: 102,517 | Gross: $50.67M
69. 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: 103,327 | Gross: $11.53M
70. Music of the Heart (1999)
PG | 124 min | Drama, Music
After Roberta Guaspari separates from her husband, she receives encouragement from her mother to take up a job of a music teacher at the Central Park East School in East Harlem.
Director: Wes Craven | Stars: Meryl Streep, Cloris Leachman, Henry Dinhofer, Michael Angarano
Votes: 13,332 | Gross: $14.86M
71. The End of the Affair (1999)
R | 102 min | Drama, Romance
A desperate man tries to find out why his beloved left him years ago.
Director: Neil Jordan | Stars: Ralph Fiennes, Julianne Moore, Stephen Rea, Heather-Jay Jones
Votes: 23,958 | Gross: $10.66M
72. Play It to the Bone (1999)
R | 124 min | Comedy, Drama, Sport
Two best friends and former middleweight contenders travel to Las Vegas to fight each other for the first time.
Director: Ron Shelton | Stars: Woody Harrelson, Antonio Banderas, Lolita Davidovich, Marie Park
Votes: 12,390 | Gross: $8.43M
73. Varsity Blues (1999)
R | 106 min | Comedy, Drama, Romance
A back-up quarterback is chosen to lead a Texas football team to victory after the star quarterback is injured.
Director: Brian Robbins | Stars: James Van Der Beek, Jon Voight, Paul Walker, Ron Lester
Votes: 49,109 | Gross: $52.89M
74. Breakfast of Champions (1999)
R | 110 min | Comedy
A rich car dealer is losing his mind. His son lives in the bomb shelter. His suicidal wife has an affair with his transvestite sales manager.
Director: Alan Rudolph | Stars: Bruce Willis, Nick Nolte, Albert Finney, Barbara Hershey
Votes: 8,250 | Gross: $0.18M
75. The Story of Us (1999)
R | 95 min | Comedy, Drama, Romance
Ben and Katie Jordan are a married couple who go through hard times in fifteen years of marriage.
Director: Rob Reiner | Stars: Bruce Willis, Michelle Pfeiffer, Colleen Rennison, Jake Sandvig
Votes: 24,990 | Gross: $27.07M
76. 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: 20,025 | Gross: $4.49M
77. 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: 178,328 | Gross: $71.58M
78. Cradle Will Rock (1999)
R | 132 min | Drama
A true story of politics and art in the 1930s U.S., focusing on a leftist musical drama and attempts to stop its production.
Director: Tim Robbins | Stars: Hank Azaria, Rubén Blades, Joan Cusack, John Cusack
Votes: 9,536 | Gross: $2.90M
79. But I'm a Cheerleader (1999)
R | 85 min | Comedy, Drama, Romance
A naive teenager is sent to rehab camp when her straitlaced parents and friends suspect her of being a lesbian.
Director: Jamie Babbit | Stars: Natasha Lyonne, Clea DuVall, Michelle Williams, Brandt Wille
Votes: 41,281 | Gross: $2.21M
80. Pushing Tin (1999)
R | 124 min | Comedy, Drama, Romance
A feud develops between two air traffic controllers: one cocky and determined while the other is restrained and laidback, which inevitably affects their lives.
Director: Mike Newell | Stars: John Cusack, Billy Bob Thornton, Cate Blanchett, Angelina Jolie
Votes: 30,464 | Gross: $8.41M
81. The Suburbans (1999)
R | 81 min | Comedy, Drama
Jennifer Love Hewitt and Will Ferrell star in this electrifying film about the reunion of a one-hitwonder new wave band from the eighties.
Director: Donal Lardner Ward | Stars: Donal Lardner Ward, Tony Guma, Craig Bierko, Will Ferrell
Votes: 2,543 | Gross: $0.01M
82. Outside Providence (1999)
R | 96 min | Comedy, Drama, Romance
After one too many run ins with the law, a punk teenager from a working class background is sent to prep school by his frustrated dad, and learns a thing or two.
Director: Michael Corrente | Stars: Shawn Hatosy, Amy Smart, Alec Baldwin, Tommy Bone
Votes: 9,326 | Gross: $7.29M
83. Detroit Rock City (1999)
R | 95 min | Adventure, Comedy, Music
In 1978, four rebellious teenagers try to scam their way into a KISS concert.
Director: Adam Rifkin | Stars: Edward Furlong, Giuseppe Andrews, James DeBello, Sam Huntington
Votes: 41,364 | Gross: $4.22M
84. P.U.N.K.S. (1999)
PG | 115 min | Comedy, Sci-Fi
A group of misfit teens evade a corrupt scientist when they steal and attempt to return a suit that delivers supernatural strength to its wearer.
Director: Sean McNamara | Stars: Tim Redwine, Kenneth A. Brown, Patrick Renna, Brandon Baker
Votes: 1,527
85. 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: 21,473 | Gross: $1.92M
86. 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: 14,925 | Gross: $4.39M
87. Snow Falling on Cedars (1999)
PG-13 | 127 min | Drama, Mystery, Romance
A Japanese-American fisherman is accused of killing his neighbor at sea. In the 1950s, race figures into the trial. So does reporter Ishmael.
Director: Scott Hicks | Stars: Ethan Hawke, Max von Sydow, Yûki Kudô, Reeve Carney
Votes: 14,568 | Gross: $14.38M
88. Angela's Ashes (1999)
R | 145 min | Biography, Drama
An Irish Catholic family returns to 1930s Limerick after a child's death in America. The unemployed I.R.A. veteran father struggles with poverty, prejudice and alcoholism as the family endures harsh slum conditions.
Director: Alan Parker | Stars: Emily Watson, Robert Carlyle, Joe Breen, Ciaran Owens
Votes: 23,256 | Gross: $13.04M
89. Dudley Do-Right (1999)
PG | 77 min | Comedy, Family, Romance
The inept Canadian Mountie Dudley Do-Right chases after villain Snidely Whiplash and woos girlfriend Nell Fenwick.
Director: Hugh Wilson | Stars: Brendan Fraser, Sarah Jessica Parker, Alfred Molina, Eric Idle
Votes: 11,390 | Gross: $9.69M
90. Cookie's Fortune (1999)
PG-13 | 118 min | Comedy, Drama
Conflict arises in the small town of Holly Springs when an old woman's death causes a variety of reactions among family and friends.
Director: Robert Altman | Stars: Glenn Close, Julianne Moore, Liv Tyler, Chris O'Donnell
Votes: 13,826 | Gross: $10.92M
91. 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: 38,998 | Gross: $39.26M
92. Tumbleweeds (1999)
PG-13 | 102 min | Comedy, Drama
A woman and her daughter have been constantly moving from town to town for years, but their newest home might be different from all the others.
Director: Gavin O'Connor | Stars: Janet McTeer, Kimberly J. Brown, Jay O. Sanders, Gavin O'Connor
Votes: 3,657 | Gross: $1.28M
93. For Love of the Game (1999)
PG-13 | 137 min | Drama, Romance, Sport
After 19 years of playing the game he's loved his whole life, Detroit Tigers pitcher Billy Chapel has to decide if he's going to risk everything and put everything out there.
Director: Sam Raimi | Stars: Kevin Costner, Kelly Preston, John C. Reilly, Jena Malone
Votes: 37,479 | Gross: $35.17M
94. Topsy-Turvy (1999)
R | 160 min | Biography, Comedy, Drama
Set in the 1880s, the story of how, during a creative dry spell, the partnership of the legendary musical/theatrical writers Gilbert and Sullivan almost dissolves, before they turn it all around and write the Mikado.
Director: Mike Leigh | Stars: Jim Broadbent, Allan Corduner, Dexter Fletcher, Sukie Smith
Votes: 13,483 | Gross: $6.20M
95. 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: 228,731 | Gross: $30.65M
96. An Ideal Husband (I) (1999)
PG-13 | 97 min | Comedy, Romance
London 1895: Cabinet minister, Sir Chiltern, and bachelor, Lord Goring, are victims of scheming women.
Director: Oliver Parker | Stars: Rupert Everett, Julianne Moore, Peter Vaughan, Minnie Driver
Votes: 16,726 | Gross: $18.54M
97. The Limey (1999)
R | 89 min | Crime, Drama, Mystery
An extremely volatile and dangerous Englishman goes to Los Angeles to find the man he considers responsible for his daughter's death.
Director: Steven Soderbergh | Stars: Terence Stamp, Peter Fonda, Lesley Ann Warren, Luis Guzmán
Votes: 34,860 | Gross: $3.19M
98. Ratcatcher (1999)
Not Rated | 94 min | Drama
A naïve young lad navigates the dirty squalid streets of 1973 Glasgow and the poor youth around him.
Director: Lynne Ramsay | Stars: Tommy Flanagan, Mandy Matthews, William Eadie, Michelle Stewart
Votes: 11,790 | Gross: $0.22M
99. 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: 102,933 | Gross: $8.26M
100. 8 ½ Women (1999)
R | 118 min | Comedy, Drama
Following the death of a mother, a father and son open up their very own harem in their Genevan estate after watching 8½ (1963).
Director: Peter Greenaway | Stars: John Standing, Matthew Delamere, Vivian Wu, Toni Collette
Votes: 4,177 | Gross: $0.42M
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