The 48 Greatest Films of 1999
by gibboanx | created - 02 Aug 2012 | updated - 08 Oct 2021 | 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: 2,322,686 | 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: 2,052,254 | Gross: $171.48M
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: 328,385 | Gross: $22.46M
4. 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: 1,210,557 | Gross: $130.10M
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: 353,284 | 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: 1,406,716 | Gross: $136.80M
7. 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: 75,139 | Gross: $16.84M
8. 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: 619,464 | Gross: $245.85M
9. 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: 169,128 | Gross: $4.86M
10. 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: 248,758 | Gross: $206.04M
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: 433,627 | Gross: $102.56M
12. 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: 214,914 | Gross: $52.04M
13. 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: 1,050,958 | Gross: $293.51M
14. 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: 285,393 | Gross: $140.54M
15. 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: 342,136 | Gross: $116.09M
16. 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: 383,815 | Gross: $101.07M
17. 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: 180,155 | Gross: $28.97M
18. 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: 178,087 | Gross: $71.58M
19. 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: 227,305 | Gross: $23.16M
20. American Movie (1999)
R | 107 min | Documentary, Comedy
Documentary about an aspiring filmmaker's attempts to finance his dream project by finally completing the low-budget horror film he abandoned years before.
Director: Chris Smith | Stars: Mark Borchardt, Mike Schank, Tom Schimmels, Monica Borchardt
Votes: 19,331 | Gross: $1.16M
21. 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: 856,174 | Gross: $474.54M
22. 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: 100,486 | Gross: $69.30M
23. 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: 73,921 | Gross: $66.38M
24. 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: 209,941 | Gross: $126.94M
25. 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: 137,455 | Gross: $34.58M
26. 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: 374,953 | Gross: $55.69M
27. 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: 34,815 | Gross: $3.19M
28. 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: 89,200
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: 460,654 | Gross: $155.25M
30. 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: 211,213 | Gross: $28.87M
31. 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: 205,102 | Gross: $38.77M
32. 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: 145,672 | Gross: $81.53M
33. 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: 91,851 | Gross: $24.36M
34. Mr. Death: The Rise and Fall of Fred A. Leuchter, Jr. (1999)
PG-13 | 91 min | Documentary, Biography
A cinematic portrait of the life and career of the infamous American execution device designer and holocaust denier.
Director: Errol Morris | Stars: Fred A. Leuchter Jr., Robert Jan Van Pelt, David Irving, Caroline Leuchter
Votes: 5,779 | Gross: $0.50M
35. 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: 40,780 | Gross: $10.56M
36. 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: 197,420 | Gross: $18.66M
37. 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: 107,171 | Gross: $2.84M
38. 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: 102,444 | Gross: $50.67M
39. Liberty Heights (1999)
R | 127 min | Comedy, Drama, Music
Baltimore, Fall 1954: Schools implement the new integration law. Ben finds the "colored" girl in his class cute - upsetting his Jewish mom and granny. Ben talks to her while his brother looks for his WASP dream girl.
Director: Barry Levinson | Stars: Adrien Brody, Bebe Neuwirth, Joe Mantegna, Ben Foster
Votes: 7,045 | Gross: $3.73M
40. 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: 287,475 | Gross: $10.82M
41. 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: 45,023 | Gross: $22.36M
42. 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: 384,991 | Gross: $38.18M
43. 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: 142,533 | Gross: $73.65M
44. 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: 234,109 | Gross: $163.48M
45. 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: 125,881 | Gross: $75.53M
46. 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: 11,838 | Gross: $34.10M
47. Bleeder (1999)
98 min | Crime, Drama
Two stories for the price of one: Lenny works in a video shop and tries to get aquainted with the waitress Lea. Leo beats his pregnant wife, Louise, which is a VERY bad idea, as her brother, Louis, is a violent racist.
Director: Nicolas Winding Refn | Stars: Kim Bodnia, Mads Mikkelsen, Rikke Louise Andersson, Liv Corfixen
Votes: 9,172
48. 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: 13,819 | Gross: $10.92M
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