Best Comedy Movies of 1999

1.

The Iron Giant

6.5
8.0/10 IMDB

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, Jennifer Aniston, Vin Diesel, Christopher McDonald, Harry Connick Jr., John Mahoney, Cloris Leachman, James Gammon, M. Emmet Walsh, Jack Angel ..
Directed by: Brad Bird
Release date: 1999-08-06
2.

Toy Story 2

6.5
7.9/10 IMDB

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, Don Rickles, Wallace Shawn, John Ratzenberger, Annie Potts, Estelle Harris ..
Directed by: John Lasseter, Lee Unkrich, Ash Brannon
Release date: 1999-10-30
3.

Office Space

6.2
7.7/10 IMDB

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, Stephen Root, Gary Cole, Richard Riehle, Alexandra Wentworth, Joe Bays ..
Directed by: Mike Judge
Release date: 1999-02-19
4.

Being John Malkovich

6.2
7.7/10 IMDB

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 its mad and controlling world of overtaking another human body.

Starring: John Cusack, Cameron Diaz, Catherine Keener, John Malkovich, Charlie Sheen, Orson Bean, Mary Kay Place, W. Earl Brown, Carlos Jacott, Willie Garson ..
Directed by: Spike Jonze
Release date: 1999-10-29
5.

South Park: Bigger, Longer & Uncut

6.1
7.7/10 IMDB

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, Franchesca Clifford, Bruce Howell, Deb Adair, Jennifer Howell, George Clooney ..
Directed by: Trey Parker
Release date: 1999-06-30
6.

10 Things I Hate About You

6.1
7.3/10 IMDB

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, Andrew Keegan, Susan May Pratt, Gabrielle Union, Larry Miller, Daryl Mitchell ..
Directed by: Gil Junger
Release date: 1999-03-30
7.

Notting Hill

6.0
7.1/10 IMDB

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, Emma Chambers, Hugh Bonneville, Richard McCabe, James Dreyfus, Dylan Moran ..
Directed by: Roger Michell
Release date: 1999-05-13
8.

Galaxy Quest

5.9
7.3/10 IMDB

The stars of a 1980s sci-fi show—now eking out 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 cast members 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, Daryl Mitchell, Enrico Colantoni, Robin Sachs, Jed Rees, Justin Long ..
Directed by: Dean Parisot
Release date: 1999-12-23
9.

Dogma

5.8
7.3/10 IMDB

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, Alan Rickman, Jason Lee, Salma Hayek, Kevin Smith, Alanis Morissette ..
Directed by: Kevin Smith
Release date: 1999-11-12
10.

Bicentennial Man

5.8
6.9/10 IMDB

Richard Martin buys a gift, a new NDR-114 robot. The product is named Andrew by the youngest of the family's children. "Bicentennial Man" follows the life and times of Andrew, a robot purchased as a household appliance programmed to perform menial tasks. As Andrew begins to experience emotions and creative thought, the Martin family soon discovers they don't have an ordinary robot.

Starring: Robin Williams, Sam Neill, Embeth Davidtz, Oliver Platt, Kiersten Warren, Wendy Crewson, Bradley Whitford, Lindze Letherman, Angela Landis, John Michael Higgins ..
Directed by: Chris Columbus
Release date: 1999-12-17

Also check Best comedy movies of 2000.

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

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