Best Movies of 1999

1.

Fight Club

7.1

A ticking-time-bomb insomniac and a slippery soap salesman channel primal male aggression into a shocking new form of therapy. Their concept catches on, with underground "fight clubs" forming in every town, until an eccentric gets in the way and ignites an out-of-control spiral toward oblivion.

Starring: Edward Norton, Brad Pitt, Helena Bonham Carter, Meat Loaf, Jared Leto
Directed by: David Fincher
Release date: 1999-10-15
2.

The Matrix

7.1

Set in the 22nd century, The Matrix tells the story of a computer hacker who joins a group of underground insurgents fighting the vast and powerful computers who now rule the earth.

Starring: Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving, Joe Pantoliano
Directed by: Lana Wachowski, Lilly Wachowski
Release date: 1999-03-30
3.

The Green Mile

7.0

A supernatural tale set on death row in a Southern prison, where gentle giant John Coffey possesses the mysterious power to heal people's ailments. When the cell block's head guard, Paul Edgecomb, recognizes Coffey's miraculous gift, he tries desperately to help stave off the condemned man's execution.

Starring: Tom Hanks, Michael Clarke Duncan, David Morse, Bonnie Hunt, James Cromwell
Directed by: Frank Darabont
Release date: 1999-12-10
4.

American Beauty

6.8

Lester Burnham, a depressed suburban father in a mid-life crisis, decides to turn his hectic life around after developing an infatuation with his daughter's attractive friend.

Starring: Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley, Mena Suvari
Directed by: Sam Mendes
Release date: 1999-09-15
5.

The Sixth Sense

6.7

A psychological thriller about an eight year old boy named Cole Sear who believes he can see into the world of the dead. A child psychologist named Malcolm Crowe comes to Cole to help him deal with his problem, learning that he really can see ghosts of dead people.

Starring: Bruce Willis, Toni Collette, Olivia Williams, Haley Joel Osment, Donnie Wahlberg
Directed by: M. Night Shyamalan
Release date: 1999-08-06
6.

The Iron Giant

6.5

In the small town of Rockwell, Maine in October 1957, a giant metal machine befriends a nine-year-old boy and ultimately finds its humanity by unselfishly saving people from their own fears and prejudices.

Starring: Eli Marienthal, Vin Diesel, Jennifer Aniston, Harry Connick Jr., Christopher McDonald
Directed by: Brad Bird
Release date: 1999-08-06
7.

Toy Story 2

6.5

Andy heads off to Cowboy Camp, leaving his toys to their own devices. Things shift into high gear when an obsessive toy collector named Al McWhiggen, owner of Al's Toy Barn kidnaps Woody. Andy's toys mount a daring rescue mission, Buzz Lightyear meets his match and Woody has to decide where he and his heart truly belong.

Starring: Tom Hanks, Tim Allen, Joan Cusack, Jim Varney, Kelsey Grammer
Directed by: John Lasseter
Release date: 1999-10-30
8.

Office Space

6.3

Three office workers strike back at their evil employers by hatching a hapless attempt to embezzle money.

Starring: Ron Livingston, Jennifer Aniston, David Herman, Ajay Naidu, Diedrich Bader
Directed by: Mike Judge
Release date: 1999-02-19
9.

Tarzan

6.2

Tarzan was a small orphan who was raised by an ape named Kala since he was a child. He believed that this was his family, but on an expedition Jane Porter is rescued by Tarzan. He then finds out that he's human. Now Tarzan must make the decision as to which family he should belong to...

Starring: Tony Goldwyn, Glenn Close, Minnie Driver, Brian Blessed, Nigel Hawthorne
Directed by: Chris Buck, Kevin Lima
Release date: 1999-06-18
10.

Being John Malkovich

6.2

One day at work, unsuccessful puppeteer Craig finds a portal into the head of actor John Malkovich. The portal soon becomes a passion for anybody who enters it's mad and controlling world of overtaking another human body.

Starring: John Cusack, Cameron Diaz, Catherine Keener, John Malkovich, Charlie Sheen
Directed by: Spike Jonze
Release date: 1999-10-29
11.

The Boondock Saints

6.2

With a God-inspired moral obligation to act against evil, twin brothers Conner and Murphy set out to rid Boston of criminals. However, rather than working within the system, these Irish Americans decide to take swift retribution into their own hands.

Starring: Willem Dafoe, Norman Reedus, Sean Patrick Flanery, David Della Rocco, David Ferry
Directed by: Troy Duffy
Release date: 1999-01-22
12.

Girl, Interrupted

6.1

Set in the changing world of the late 1960s, Susanna Kaysen's prescribed "short rest" from a psychiatrist she had met only once becomes a strange, unknown journey into Alice's Wonderland, where she struggles with the thin line between normal and crazy. Susanna soon realizes how hard it is to get out once she has been committed, and she ultimately has to choose between the world of people who belong inside or the difficult world of reality outside.

Starring: Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy, Elisabeth Moss
Directed by: James Mangold
Release date: 1999-12-21
13.

South Park: Bigger, Longer & Uncut

6.1

When the four boys see an R-rated movie featuring Canadians Terrance and Philip, they are pronounced "corrupted", and their parents pressure the United States to wage war against Canada.

Starring: Matt Stone, Mary Kay Bergman, Isaac Hayes, Jesse Brant Howell, Anthony Cross-Thomas
Directed by: Trey Parker
Release date: 1999-06-30
14.

Eyes Wide Shut

6.1

After Dr. Bill Hartford's wife, Alice, admits to having sexual fantasies about a man she met, Bill becomes obsessed with having a sexual encounter. He discovers an underground sexual group and attends one of their meetings -- and quickly discovers that he is in over his head.

Starring: Tom Cruise, Nicole Kidman, Madison Eginton, Jackie Sawiris, Sydney Pollack
Directed by: Stanley Kubrick
Release date: 1999-07-16
15.

10 Things I Hate About You

6.1

On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own.

Starring: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz
Directed by: Gil Junger
Release date: 1999-03-30
16.

Sleepy Hollow

6.0

New York detective Ichabod Crane is sent to Sleepy Hollow to investigate a series of mysterious deaths in which the victims are found beheaded. But the locals believe the culprit to be none other than the ghost of the legendary Headless Horseman.

Starring: Johnny Depp, Ian McDiarmid, Christina Ricci, Casper Van Dien, Michael Gough
Directed by: Tim Burton
Release date: 1999-11-18
17.

The Talented Mr. Ripley

6.0

Tom Ripley is a calculating young man who believes it's better to be a fake somebody than a real nobody. Opportunity knocks in the form of a wealthy U.S. shipbuilder who hires Tom to travel to Italy to bring back his playboy son, Dickie. Ripley worms his way into the idyllic lives of Dickie and his girlfriend, plunging into a daring scheme of duplicity, lies and murder.

Starring: Matt Damon, Gwyneth Paltrow, Jude Law, Cate Blanchett, Philip Seymour Hoffman
Directed by: Anthony Minghella
Release date: 1999-12-25
18.

Notting Hill

6.0

William Thacker is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.

Starring: Julia Roberts, Hugh Grant, Gina McKee, Tim McInnerny, Rhys Ifans
Directed by: Roger Michell
Release date: 1999-05-13
19.

Galaxy Quest

5.9

The stars of a 1970s sci-fi show - now scraping a living through re-runs and sci-fi conventions - are beamed aboard an alien spacecraft. Believing the cast's heroic on-screen dramas are historical documents of real-life adventures, the band of aliens turn to the ailing celebrities for help in their quest to overcome the oppressive regime in their solar system.

Starring: Tim Allen, Sigourney Weaver, Alan Rickman, Tony Shalhoub, Sam Rockwell
Directed by: Dean Parisot
Release date: 1999-12-23
20.

Dogma

5.8

The latest battle in the eternal war between Good and Evil has come to New Jersey in the late, late 20th Century. Angels, demons, apostles and prophets (of a sort) walk among the cynics and innocents of America and duke it out for the fate of humankind.

Starring: Ben Affleck, Matt Damon, Linda Fiorentino, Jason Mewes, Chris Rock
Directed by: Kevin Smith
Release date: 1999-11-12

Also check Best movies of 1998.

Check out our top containing the Best Movies of 1999. This top was obtained with our unique algorithm ordered by our unique ranking system.

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