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1.
Overview:
Office Space is a 1999 American satirical black comedy film written and directed by Mike Judge. It satirizes the work life of a typical 1990s software company, focusing on a handful of individuals weary ...
Release date: 19 February 1999
Genre:
Comedy, Crime, Romance
Three company workers who hate their jobs decide to rebel against their greedy boss.
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2.
Overview:
Idle Hands is a 1999 American teen horror comedy film directed by Rodman Flender, written by Terri Hughes and Ron Milbauer, and starring Devon Sawa, Seth Green, Elden Henson, Jessica Alba, and Vivica A ...
Release date: 30 April 1999
Genre:
Comedy, Fantasy, Horror, Mystery, Sci-Fi, Thriller
A teenage slacker's right hand becomes possessed with murderous intent.
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3.
Overview:
Fight Club is a 1999 American film directed by David Fincher and starring Brad Pitt, Edward Norton, and Helena Bonham Carter. It is based on a 1996 novel by Chuck Palahniuk. Norton plays the unnamed n ...
Release date: 10 September 1999
Genre:
Crime, Drama, Thriller
An insomniac office worker and a devil-may-care soap maker form an underground fight club that evolves into much more.
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4.
Overview:
Drop Dead Gorgeous is a 1999 American satirical mockumentary black comedy film directed by Michael Patrick Jann and written by Lona Williams. It stars Kirsten Dunst, Ellen Barkin, Brittany Murphy, Allison ...
Release date: 9 July 1999
Genre:
Comedy
A small-town beauty pageant turns deadly as it becomes clear that someone will go to any lengths to win.
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5.
Overview:
American Beauty is a 1999 American psychological black comedy-drama film written by Alan Ball and directed by Sam Mendes in his feature directorial debut. Kevin Spacey stars as Lester Burnham, an adve ...
Release date: 8 September 1999
Genre:
Drama
A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend.
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6.
Overview:
Three Kings is a 1999 American black comedy war film written and directed by David O. Russell from a story by John Ridley. It stars George Clooney, Mark Wahlberg, Ice Cube, and Spike Jonze as four American ...
Release date: 27 September 1999
Genre:
Action, Adventure, Comedy, War
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 ...
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7.
Overview:
Jawbreaker is a 1999 American teen black comedy crime film written and directed by Darren Stein. The film stars Rose McGowan, Rebecca Gayheart, and Julie Benz as girls in an exclusive clique in their high ...
Release date: 30 January 1999
Genre:
Comedy, Crime, Thriller
Three of the most popular girls at Reagan High accidentally kill the prom queen with a jawbreaker when a kidnapping goes horribly wrong.
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8.
Overview:
Analyze This is a 1999 American crime comedy film directed by Harold Ramis, who co-wrote the screenplay with playwright Kenneth Lonergan and Peter Tolan. The plot follows a crisis-stricken mafioso (Robert ...
Release date: 5 March 1999
Genre:
Comedy, Crime
A comedy about a psychiatrist whose number-one patient is an insecure mob boss.
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9.
Overview:
Teaching Mrs. Tingle is a 1999 American teen black comedy thriller film written and directed by Kevin Williamson, in his directorial debut, and starring Helen Mirren, Katie Holmes, Marisa Coughlan, Barry ...
Release date: 11 August 1999
Genre:
Comedy, Thriller
The story of a girl who is willing to do anything to become Valedictorian, even if it means murdering the teacher that stands in her way.
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10.
Overview:
Plunkett & Macleane is a 1999 British historical action comedy film directed by Jake Scott, and starring Robert Carlyle, Jonny Lee Miller and Liv Tyler. Gary Oldman was executive producer.
Release date: 22 January 1999
Genre:
Action, Drama, Adventure
Will Plunkett and Captain James Macleane, two men from different ends of the social spectrum in 18th-century England...
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11.
Overview:
Election is a 1999 American black comedy film directed by Alexander Payne from a screenplay by Payne and Jim Taylor, based on Tom Perrotta's 1998 novel.
Release date: 23 April 1999
Genre:
Comedy, Drama, Romance
A high school teacher meets his match in an over-achieving student politician.
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12.
Overview:
Cookie's Fortune is a 1999 American black comedy film directed by Robert Altman and starring Glenn Close, Julianne Moore, Liv Tyler, Patricia Neal, Charles S. Dutton, and Chris O'Donnell. It follows a ...
Release date: 22 January 1999
Genre:
Comedy, Drama, Crime
Conflict arises in the small town of Holly Springs when an old woman's death causes a variety of reactions among family and friends.
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13.
Overview:
Breakfast of Champions is a 1999 American satirical black comedy film adapted and directed by Alan Rudolph, from Kurt Vonnegut, Jr.'s 1973 novel. Though the producers entered it into the 49th Berlin I ...
Release date: 13 February 1999
Genre:
Comedy
A rich car dealer is losing his mind. His son lives in the bomb shelter. His suicidal wife has an affair with his transvestite sales manager.
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14.
Overview:
South Park: Bigger, Longer & Uncut is a 1999 American adult animated musical comedy film based on the animated sitcom South Park. The film was directed by series creator Trey Parker from a screenplay ...
Release date: 30 June 1999
Genre:
Animation, Comedy, Musical
When the four boys see an R-rated movie featuring Canadians Terrance & Phillip, they are pronounced "corrupted", and their parents pressure the ...
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15.
Overview:
Ravenous is a 1999 horror comedy Western cannibal film starring Guy Pearce, Robert Carlyle, Jeffrey Jones and David Arquette. The film, which is set in 1840s California, was directed by Antonia Bird and ...
Release date: 16 March 1999
Genre:
Horror, Thriller
In a remote military outpost in the 19th century, Captain John Boyd and his regiment embark on a rescue mission which takes a dark turn when they are ...
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16.
Overview:
Guest House Paradiso is a 1999 British slapstick black comedy film written by and starring comic duo Rik Mayall and Adrian Edmondson, who also directed in his feature directorial debut.
Release date: 3 December 1999
Genre:
Comedy, Thriller
Richie and Eddie, a perverted loser and his alcoholic partner in crime, run the worst hotel in Britain: the Guest House Paradiso.
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17.
Overview:
Five Aces is a 1999 black comedy drama film written, produced and directed by David Michael O'Neill. It stars Charlie Sheen, Christopher McDonald, Jeff Cesario, Michael McGrady, Tia Carrere, Geoffrey Lewis ...
Release date: 28 May 1999
Genre:
Drama, Comedy
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18.
Overview:
In Bed with Santa (Swedish: Tomten är far till alla barnen, "Santa is the father to all the children") is a Swedish black comedy film which was released to cinemas in Sweden on 26 November 1999, directed ...
Release date: 26 November 1999
Genre:
Comedy
In what has to be one of the worst ideas in Christmas party planning history, Swedish house wife Sara...
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19.
Overview:
Scarfies (released as Crime 101 in the United States) is a 1999 New Zealand black comedy film set in the southern university city of Dunedin. The film's original title comes from the local nickname for ...
Release date: 22 July 1999
Genre:
Comedy, Thriller, Action
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20.
Overview:
Parting Shots is a 1999 British dark comedy film starring Chris Rea, Felicity Kendal, Oliver Reed, Bob Hoskins, Diana Rigg, Ben Kingsley, John Cleese and Joanna Lumley. It was the final film directed by ...
Release date: 1 May 1998
Genre:
Comedy, Crime, Romance
After learning he is dying from cancer an failed photographer illegally buys a pistol and decides to go vigilante and get his revenge on all those who ...
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