1999
by ff750387 | created - 28 Jun 2014 | updated - 19 Jul 2018 | Public- Instant Watch Options
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1. 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: 180,085 | Gross: $28.97M
2. 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: 107,109 | Gross: $2.84M
3. 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: 2,050,420 | Gross: $171.48M
4. 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: 145,567 | Gross: $81.53M
5. One Day in September (1999)
R | 94 min | Documentary, History, Sport
The Palestinian terrorist group Black September holds Israeli athletes hostage at the 1972 Summer Olympic Games in Munich.
Director: Kevin Macdonald | Stars: Michael Douglas, Ankie Spitzer, Jamal Al Gashey, Gerald Seymour
Votes: 6,240 | Gross: $0.16M
6. 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: 2,320,413 | Gross: $37.03M
7. 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: 374,671 | Gross: $55.69M
8. 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: 328,215 | Gross: $22.46M
9. 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: 91,809 | Gross: $24.36M
10. 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: 1,209,866 | Gross: $130.10M
11. 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: 97,367 | Gross: $6.20M
12. 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: 76,001 | Gross: $16.64M
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: 353,158 | Gross: $22.86M
14. 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: 287,314 | Gross: $10.82M
15. Gloria (1999)
R | 108 min | Crime, Drama, Thriller
After serving three years in prison covering for her gangster boyfriend, Kevin, Gloria returns to New York City for the money she was promised. Inside Kevin's base of operations, she finds 7-year-old Nicky, whose family has been killed.
Director: Sidney Lumet | Stars: Sharon Stone, Jean-Luke Figueroa, Jeremy Northam, Cathy Moriarty
Votes: 6,214 | Gross: $4.16M
16. 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: 142,627 | Gross: $36.66M
17. 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: 240,976 | Gross: $81.30M
18. 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: 161,581 | Gross: $106.89M
19. 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: 180,362 | Gross: $60.65M
20. 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: 100,390 | Gross: $69.30M
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: 855,629 | Gross: $474.54M
22. 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: 123,853 | Gross: $87.70M
23. 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: 30,446 | Gross: $8.41M
24. 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: 250,477 | Gross: $0.03M
25. 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: 383,636 | Gross: $101.07M
26. 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: 125,837 | Gross: $75.53M
27. 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: 209,888 | Gross: $126.94M
28. 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: 1,050,247 | Gross: $293.51M
29. 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: 24,972 | Gross: $27.07M
30. 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: 103,732 | Gross: $63.37M
31. 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: 148,818 | Gross: $140.04M
32. 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: 228,514 | Gross: $30.65M
33. 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: 433,364 | Gross: $102.56M
34. 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: 248,604 | Gross: $206.04M
35. 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: 227,058 | Gross: $23.16M
36. 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: 1,405,605 | Gross: $136.80M
37. 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: 204,983 | Gross: $38.77M
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