1999 Ranked
by johnbradyla | created - 01 Jun 2015 | updated - 01 Dec 2016 | Public- Instant Watch Options
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1. 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: 385,141 | Gross: $38.18M
2. 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: 1,210,852 | Gross: $130.10M
3. 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: 433,735 | Gross: $102.56M
4. 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: 248,808 | Gross: $206.04M
5. Baby Geniuses (1999)
PG | 97 min | Comedy, Crime, Family
Scientists hold super intelligent talking babies captive, but things take a turn for the worse when a mix-up occurs between a baby genius and its twin.
Director: Bob Clark | Stars: Kathleen Turner, Christopher Lloyd, Kim Cattrall, Peter MacNicol
Votes: 27,642 | Gross: $27.14M
6. 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: 234,174 | Gross: $163.48M
7. 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: 285,475 | Gross: $140.54M
8. 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: 71,714 | Gross: $26.49M
9. 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: 88,766 | Gross: $68.52M
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: 73,932 | Gross: $66.38M
11. 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: 205,140 | Gross: $38.77M
12. 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: 41,337 | Gross: $4.22M
13. 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: 228,628 | Gross: $30.65M
14. 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: 11,386 | Gross: $9.69M
15. 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: 2,323,420 | Gross: $37.03M
16. 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: 178,144 | Gross: $71.58M
17. 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: 75,150 | Gross: $16.84M
18. 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: 46,742 | Gross: $4.00M
19. 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: 50,866 | Gross: $97.40M
20. 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: 54,763 | Gross: $63.84M
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: 328,432 | Gross: $22.46M
22. The Matrix (1999)
R | 136 min | Action, Sci-Fi
When a beautiful stranger leads computer hacker Neo to a forbidding underworld, he discovers the shocking truth--the life he knows is the elaborate deception of an evil cyber-intelligence.
Directors: Lana Wachowski, Lilly Wachowski | Stars: Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving
Votes: 2,052,771 | Gross: $171.48M
23. The Mod Squad (1999)
R | 92 min | Action, Crime, Thriller
Three problem teens sent to jail are offered a deal to work with an undercover cop, uncover an intricate drug ring and are caught in a deadly set-up. With cops on their trail, they have little time to solve the case and clear their names.
Director: Scott Silver | Stars: Claire Danes, Omar Epps, Giovanni Ribisi, Dennis Farina
Votes: 9,502 | Gross: $13.26M
24. 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: 460,854 | Gross: $155.25M
25. 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: 70,631 | Gross: $29.76M
26. 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: 98,025 | Gross: $32.48M
27. 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: 287,533 | Gross: $10.82M
28. 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: 103,804 | Gross: $63.37M
29. 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: 14,920 | Gross: $4.39M
30. 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: 1,051,194 | Gross: $293.51M
31. South Park: Bigger, Longer & Uncut (1999)
R | 81 min | Animation, Comedy, Fantasy
When Stan Marsh and his friends go see an R-rated movie, they start cursing and their parents think that Canada is to blame.
Director: Trey Parker | Stars: Trey Parker, Matt Stone, Mary Kay Bergman, Isaac Hayes
Votes: 214,948 | Gross: $52.04M
32. 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: 856,331 | Gross: $474.54M
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: 148,969 | Gross: $140.04M
34. 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: 20,379 | Gross: $30.63M
35. 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: 49,060 | Gross: $52.89M
36. 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: 167,281 | Gross: $113.81M
37. 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: 619,567 | Gross: $245.85M
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