1999 Films
by jordycastille | created - 27 Oct 2012 | updated - 6 months ago | Public- Instant Watch Options
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1. 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: 2,325,249 | Gross: $37.03M
2. 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: 2,054,227 | Gross: $171.48M
3. 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: 1,211,322 | Gross: $130.10M
4. 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: 1,408,069 | Gross: $136.80M
5. 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: 433,942 | Gross: $102.56M
6. 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: 856,815 | Gross: $474.54M
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: 287,697 | 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: 1,051,734 | Gross: $293.51M
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: 385,565 | Gross: $38.18M
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: 384,017 | Gross: $101.07M
11. 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: 250,750 | Gross: $0.03M
12. 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: 210,013 | Gross: $126.94M
13. 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: 461,341 | Gross: $155.25M
14. 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: 375,323 | Gross: $55.69M
15. 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: 328,605 | Gross: $22.46M
16. 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: 285,706 | Gross: $140.54M
17. 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: 205,244 | Gross: $38.77M
18. House on Haunted Hill (1999)
R | 93 min | Horror, Mystery, Thriller
An amusement park mogul offers a group of diverse people $1,000,000 to spend the night in a haunted house with a horrifying past.
Director: William Malone | Stars: Geoffrey Rush, Famke Janssen, Taye Diggs, Peter Gallagher
Votes: 60,154 | Gross: $40.85M
19. 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: 211,429 | Gross: $28.87M
20. 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: 619,920 | Gross: $245.85M
21. 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: 234,293 | Gross: $163.48M
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: 228,705 | Gross: $30.65M
23. 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: 178,291 | Gross: $71.58M
24. 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: 342,407 | Gross: $116.09M
25. 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: 197,565 | Gross: $18.66M
26. 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: 353,438 | Gross: $22.86M
27. 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: 169,288 | Gross: $4.86M
28. 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: 180,265 | Gross: $28.97M
29. The Thomas Crown Affair (1999)
R | 113 min | Crime, Romance, Thriller
A very rich and successful playboy amuses himself by stealing artwork, but may have met his match in a seductive detective.
Director: John McTiernan | Stars: Pierce Brosnan, Rene Russo, Denis Leary, Ben Gazzara
Votes: 100,616 | Gross: $69.30M
30. 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: 103,311 | Gross: $11.53M
31. 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: 185,051 | Gross: $66.52M
32. 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: 248,921 | Gross: $206.04M
33. 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: 103,856 | Gross: $63.37M
34. 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: 80,505 | Gross: $91.41M
35. 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: 125,913 | Gross: $75.53M
36. 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: 247,353 | Gross: $171.09M
37. 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: 243,437 | Gross: $81.30M
38. 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: 132,143 | Gross: $32.70M
39. End of Days (1999)
R | 122 min | Action, Fantasy, Horror
At the end of the century, Satan visits New York in search of a bride. It's up to an ex-cop who now runs an elite security outfit to stop him.
Director: Peter Hyams | Stars: Arnold Schwarzenegger, Gabriel Byrne, Robin Tunney, Kevin Pollak
Votes: 116,747 | Gross: $66.89M
40. Message in a Bottle (1999)
PG-13 | 126 min | Drama, Romance
A woman discovers a tragic love letter in a bottle on a beach, and is determined to track down its author.
Director: Luis Mandoki | Stars: Kevin Costner, Robin Wright, Paul Newman, John Savage
Votes: 40,374 | Gross: $52.88M
41. Stir of Echoes (1999)
R | 99 min | Horror, Mystery, Thriller
After being hypnotized by his sister-in-law, a man begins seeing haunting visions of a girl's ghost and a mystery begins to unfold around him.
Director: David Koepp | Stars: Kevin Bacon, Zachary David Cope, Kathryn Erbe, Illeana Douglas
Votes: 87,532 | Gross: $21.13M
42. The Thirteenth Floor (1999)
R | 100 min | Mystery, Sci-Fi, Thriller
A computer scientist running a virtual reality simulation of 1937 becomes the primary suspect when his colleague and mentor is murdered.
Director: Josef Rusnak | Stars: Craig Bierko, Gretchen Mol, Armin Mueller-Stahl, Vincent D'Onofrio
Votes: 77,309 | Gross: $15.50M
43. Payback (I) (1999)
R | 100 min | Action, Crime, Drama
After a successful heist, Porter is left for dead. Once he recovers, he seeks vengeance and wants his share of the money.
Director: Brian Helgeland | Stars: Mel Gibson, Gregg Henry, Maria Bello, David Paymer
Votes: 145,763 | Gross: $81.53M
44. 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: 104,830 | Gross: $57.55M
45. 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: 41,319 | Gross: $19.28M
46. 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: 97,591 | Gross: $55.47M
47. 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: 167,320 | Gross: $113.81M
48. 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: 227,590 | Gross: $23.16M
49. 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: 142,772 | Gross: $36.66M
50. 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: 49,096 | Gross: $52.89M
51. 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: 180,517 | Gross: $60.65M
52. 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: 142,600 | Gross: $73.65M
53. 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: 57,447 | Gross: $10.67M
54. 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: 40,829 | Gross: $10.56M
55. 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: 137,521 | Gross: $34.58M
56. 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: 149,093 | Gross: $140.04M
57. 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: 69,718 | Gross: $14.28M
58. October Sky (1999)
PG | 108 min | Biography, Drama, Family
The true story of Homer Hickam, a coal miner's son who was inspired by the first Sputnik launch to take up rocketry against his father's wishes.
Director: Joe Johnston | Stars: Jake Gyllenhaal, Chris Cooper, Laura Dern, Chris Owen
Votes: 98,084 | Gross: $32.48M
59. 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: 107,246 | Gross: $2.84M
60. 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: 124,724 | Gross: $58.22M
61. 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: 102,508 | Gross: $50.67M
62. 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: 76,076 | Gross: $16.64M
63. 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: 96,995 | Gross: $3.31M
64. 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: 123,934 | Gross: $87.70M
65. 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: 215,024 | Gross: $52.04M
66. 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: 161,723 | Gross: $106.89M
67. 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: 46,770 | Gross: $4.00M
68. 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: 80,000 | Gross: $65.54M
69. 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: 75,175 | Gross: $16.84M
70. Blue Streak (1999)
PG-13 | 93 min | Action, Comedy, Crime
A former convict poses as a cop to retrieve a diamond he stole years ago.
Director: Les Mayfield | Stars: Martin Lawrence, Luke Wilson, Peter Greene, Dave Chappelle
Votes: 88,803 | Gross: $68.52M
71. 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: 21,300 | Gross: $17.85M
72. 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: 104,568 | Gross: $14.88M
73. Arlington Road (1999)
R | 117 min | Action, Crime, Drama
A man begins to suspect his neighbors are not what they appear to be and their secrets could be deadly.
Director: Mark Pellington | Stars: Jeff Bridges, Tim Robbins, Joan Cusack, Hope Davis
Votes: 91,906 | Gross: $24.36M
74. 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: 71,758 | Gross: $26.49M
75. The Wood (1999)
R | 106 min | Comedy, Drama, Romance
While dealing with a friend's cold feet on his wedding day, a writer reminisces about his youth with his best friends.
Director: Rick Famuyiwa | Stars: Elayn J. Taylor, Omar Epps, Richard T. Jones, Sean Nelson
Votes: 10,208 | Gross: $25.05M
76. 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: 72,286 | Gross: $50.05M
77. Mystery Men (1999)
PG-13 | 121 min | Action, Comedy, Fantasy
A group of inept amateur superheroes must try to save the day when a supervillain threatens to destroy a major superhero and the city.
Director: Kinka Usher | Stars: Ben Stiller, Janeane Garofalo, William H. Macy, Hank Azaria
Votes: 70,644 | Gross: $29.76M
78. 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: 54,801 | Gross: $63.84M
79. Double Jeopardy (1999)
R | 105 min | Crime, Drama, Mystery
A woman framed for her husband's murder suspects he is still alive; as she has already been tried for the crime, she can't be re-prosecuted if she finds and kills him.
Director: Bruce Beresford | Stars: Ashley Judd, Tommy Lee Jones, Bruce Greenwood, Benjamin Weir
Votes: 95,930 | Gross: $116.74M
80. 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: 26,982 | Gross: $16.07M
81. 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: 28,956 | Gross: $3.07M
82. Superstar (1999)
PG-13 | 81 min | Comedy, Romance
A nerdy Catholic schoolgirl, Mary Katherine Gallagher, dreams of superstardom.
Director: Bruce McCulloch | Stars: Molly Shannon, Will Ferrell, Elaine Hendrix, Harland Williams
Votes: 20,382 | Gross: $30.63M
83. Lake Placid (1999)
R | 82 min | Action, Comedy, Horror
Four people attempt to stop a gigantic crocodile, who is terrorizing residents in Black Lake, Maine.
Director: Steve Miner | Stars: Bridget Fonda, Bill Pullman, Oliver Platt, Brendan Gleeson
Votes: 65,565 | Gross: $31.77M
84. Runaway Bride (1999)
PG | 116 min | Comedy, Romance
A reporter is assigned to write a story about a woman who has left a string of fiancés at the altar.
Director: Garry Marshall | Stars: Julia Roberts, Richard Gere, Joan Cusack, Hector Elizondo
Votes: 104,530 | Gross: $152.26M
85. 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
86. 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: 24,987 | Gross: $27.07M
87. 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: 97,501 | Gross: $6.20M
88. The Rage: Carrie 2 (1999)
R | 104 min | Drama, Horror, Sci-Fi
A horrible massacre strikes up after an outcast teenage girl is taunted by a group of high school jocks, all of them unaware of her cutthroat telekinetic powers.
Directors: Katt Shea, Robert Mandel | Stars: Emily Bergl, Jason London, Dylan Bruno, J. Smith-Cameron
Votes: 17,890 | Gross: $17.76M
89. 200 Cigarettes (1999)
R | 101 min | Comedy, Drama, Romance
A collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses.
Director: Risa Bramon Garcia | Stars: Ben Affleck, Casey Affleck, Dave Chappelle, Guillermo Diaz
Votes: 16,350 | Gross: $6.85M
90. 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: 73,969 | Gross: $66.38M
91. 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: 41,361 | Gross: $4.22M
92. 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: 63,865 | Gross: $102.71M
93. 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: 38,993 | Gross: $39.26M
94. 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: 37,474 | Gross: $35.17M
95. Brokedown Palace (1999)
PG-13 | 100 min | Drama, Mystery, Thriller
Two women are arrested for smuggling while vacationing in Thailand.
Director: Jonathan Kaplan | Stars: Claire Danes, Kate Beckinsale, Bill Pullman, Jacqueline Kim
Votes: 24,057 | Gross: $10.11M
96. 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: 36,689 | Gross: $4.20M
97. True Crime (1999)
R | 127 min | Crime, Drama, Mystery
Can an over-the-hill journalist uncover the evidence that can prove a death row inmate's innocence just hours before his execution?
Director: Clint Eastwood | Stars: Clint Eastwood, Isaiah Washington, LisaGay Hamilton, James Woods
Votes: 38,535 | Gross: $16.64M
98. 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: 23,946 | Gross: $10.66M
99. 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: 21,470 | Gross: $1.92M
100. Universal Soldier: The Return (1999)
R | 83 min | Action, Sci-Fi
The "universal soldiers" must fight the whole army, when the military's supercomputer S.E.T.H gets out of control.
Director: Mic Rodgers | Stars: Jean-Claude Van Damme, Bill Goldberg, Heidi Schanz, Michael Jai White
Votes: 30,781 | Gross: $10.43M
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