1999 Films
by scmp2000 | created - 07 Jan 2013 | updated - 07 Apr 2020 | 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: 385,565 | 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: 1,211,322 | Gross: $130.10M
3. 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
4. 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
5. 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
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: 2,325,249 | Gross: $37.03M
7. 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
8. 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
9. 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
10. 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
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: 97,501 | Gross: $6.20M
12. 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
13. 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
14. 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
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 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
17. 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
18. 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
19. 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
20. 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
21. Mansfield Park (1999)
PG-13 | 112 min | Comedy, Drama, Romance
Fanny, born into a poor family, is sent away to live with wealthy uncle Sir Thomas, his wife and their four children, where she'll be brought up for a proper introduction to society.
Director: Patricia Rozema | Stars: Frances O'Connor, Jonny Lee Miller, Alessandro Nivola, Hannah Taylor Gordon
Votes: 25,847 | Gross: $4.76M
22. 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
23. 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
24. 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
25. 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
26. 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
27. 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
28. 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
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: 384,017 | Gross: $101.07M
30. 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: 34,851 | Gross: $3.19M
31. All About My Mother (1999)
R | 101 min | Comedy, Drama, Romance
A comedy-drama about a bereaved mother, and overwrought actress, her jealous lover, and a pregnant nun.
Director: Pedro Almodóvar | Stars: Cecilia Roth, Marisa Paredes, Candela Peña, Antonia San Juan
Votes: 102,914 | Gross: $8.26M
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