1999 Movies Ranked
by nickfrie | created - 13 Jan 2016 | updated - 15 Feb 2022 | 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: 1,211,450 | 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: 2,325,703 | Gross: $37.03M
3. 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: 328,634 | Gross: $22.46M
4. 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: 215,037 | Gross: $52.04M
5. 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: 1,408,415 | Gross: $136.80M
6. 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: 2,054,642 | Gross: $171.48M
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: 287,741 | 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: 1,051,880 | Gross: $293.51M
9. 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: 180,527 | Gross: $60.65M
10. 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: 620,038 | Gross: $245.85M
11. 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: 433,990 | Gross: $102.56M
12. 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: 385,651 | Gross: $38.18M
13. 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: 353,461 | Gross: $22.86M
14. 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: 104,577 | Gross: $14.88M
15. 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: 97,526 | Gross: $6.20M
16. 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: 125,918 | Gross: $75.53M
17. 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: 250,767 | Gross: $0.03M
18. 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: 234,313 | Gross: $163.48M
19. The War Zone (1999)
R | 98 min | Drama, Thriller
An alienated teenager, saddened that he has moved away from London, must find a way to deal with a dark family secret.
Director: Tim Roth | Stars: Ray Winstone, Annabelle Apsion, Kate Ashfield, Lara Belmont
Votes: 11,197 | Gross: $0.25M
20. 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: 180,294 | Gross: $28.97M
21. 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: 98,091 | Gross: $32.48M
22. 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: 211,477 | Gross: $28.87M
23. 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: 461,424 | Gross: $155.25M
24. 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: 227,649 | Gross: $23.16M
25. Life Is Beautiful (1997)
PG-13 | 116 min | Comedy, Drama, Romance
When an open-minded Jewish waiter and his son become victims of the Holocaust, he uses a perfect mixture of will, humor and imagination to protect his son from the dangers around their camp.
Director: Roberto Benigni | Stars: Roberto Benigni, Nicoletta Braschi, Giorgio Cantarini, Giustino Durano
Votes: 743,609 | Gross: $57.60M
26. 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: 75,204 | Gross: $16.84M
27. 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: 243,641 | Gross: $81.30M
28. 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: 88,808 | Gross: $68.52M
29. 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: 384,062 | Gross: $101.07M
30. 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: 149,106 | Gross: $140.04M
31. 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: 375,381 | Gross: $55.69M
32. 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: 285,759 | Gross: $140.54M
33. 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: 142,784 | Gross: $36.66M
34. Following (1998)
R | 69 min | Crime, Mystery, Thriller
A young writer who follows strangers for material meets a thief who takes him under his wing.
Director: Christopher Nolan | Stars: Jeremy Theobald, Alex Haw, Lucy Russell, John Nolan
Votes: 101,812 | Gross: $0.05M
35. Rushmore (1998)
R | 93 min | Comedy, Drama, Romance
A teenager at Rushmore Academy falls for a much older teacher and befriends a middle-aged industrialist. Later, he finds out that his love interest and his friend are having an affair, which prompts him to begin a vendetta.
Director: Wes Anderson | Stars: Jason Schwartzman, Bill Murray, Olivia Williams, Seymour Cassel
Votes: 198,052 | Gross: $17.11M
36. Audition (1999)
R | 115 min | Drama, Horror, Mystery
A widower takes an offer to screen girls at a special audition, arranged for him by a friend to find him a new wife. The one he fancies is not who she appears to be after all.
Director: Takashi Miike | Stars: Ryo Ishibashi, Eihi Shiina, Tetsu Sawaki, Jun Kunimura
Votes: 89,297
37. 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: 76,086 | Gross: $16.64M
38. Run Lola Run (1998)
R | 80 min | Action, Crime, Thriller
After a botched money delivery, Lola has 20 minutes to come up with 100,000 Deutschmarks.
Director: Tom Tykwer | Stars: Franka Potente, Moritz Bleibtreu, Herbert Knaup, Nina Petri
Votes: 207,080 | Gross: $7.27M
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