Best Comedy Movies of 1999

1.

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
2.

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
3.

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
4.

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
5.

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
6.

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
7.

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
8.

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
9.

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
10.

Bicentennial Man

5.7

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
Directed by: Chris Columbus
Release date: 1999-12-17
11.

American Pie

5.6

At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to all "score." by their senior prom.

Starring: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Alyson Hannigan, Shannon Elizabeth
Directed by: Paul Weitz, Chris Weitz
Release date: 1999-07-09
12.

Man on the Moon

5.4

A film about the life and career of the eccentric avant-garde comedian, Andy Kaufman.

Starring: Jim Carrey, Courtney Love, Bob Zmuda, Danny DeVito, Gerry Becker
Directed by: Miloš Forman
Release date: 1999-12-22
13.

Austin Powers: The Spy Who Shagged Me

5.3

When diabolical genius, Dr. Evil travels back in time to steal superspy Austin Powers's ‘mojo’, Austin must return to the swingin' '60s himself – with the help of American agent, Felicity Shagwell – to stop the dastardly plan. Once there, Austin faces off against Dr. Evil's army of minions and saves the world in his own unbelievably groovy way.

Starring: Mike Myers, Heather Graham, Michael York, Robert Wagner, Rob Lowe
Directed by: Jay Roach
Release date: 1999-06-08
14.

Big Daddy

5.3

A lazy law school grad adopts a kid to impress his girlfriend, but everything doesn't go as planned and he becomes the unlikely foster father.

Starring: Adam Sandler, Joey Lauren Adams, Kristy Swanson, Cole Sprouse, Jon Stewart
Directed by: Dennis Dugan
Release date: 1999-06-25
15.

Go

5.2

Told from three perspectives, a story of a bunch of young Californians trying to get some cash, do and deal some drugs, score money and sex in Las Vegas, and generally experience the rush of life.

Starring: Sarah Polley, Katie Holmes, Jay Mohr, Timothy Olyphant, William Fichtner
Directed by: Doug Liman
Release date: 1999-04-09
16.

Three Kings

5.2

A group of American soldiers stationed in Iraq at the end of the Gulf War find a map they believe will take them to a huge cache of stolen Kuwaiti gold hidden near their base, and they embark on a secret mission that's destined to change everything.

Starring: George Clooney, Mark Wahlberg, Ice Cube, Spike Jonze, Cliff Curtis
Directed by: David O. Russell
Release date: 1999-09-27
17.

Sweet and Lowdown

5.1

A comedic biopic focused on the life of fictional jazz guitarist Emmett Ray. Ray was an irresponsible, free-spending, arrogant, obnoxious, alcohol-abusing, miserable human being, who was also arguably the best guitarist in the world.

Starring: Sean Penn, Samantha Morton, Anthony LaPaglia, Uma Thurman, James Urbaniak
Directed by: Woody Allen
Release date: 1999-12-03
18.

Election

5.1

A high school teacher's personal life becomes complicated as he works with students during the school elections.

Starring: Matthew Broderick, Reese Witherspoon, Chris Klein, Jessica Campbell, Mark Harelik
Directed by: Alexander Payne
Release date: 1999-04-23
19.

Human Traffic

5.1

Five twenty-something friends spend a drug-fueled weekend in Cardiff, Wales.

Starring: John Simm, Shaun Parkes, Nicola Reynolds, Lorraine Pilkington, Danny Dyer
Directed by: Justin Kerrigan
Release date: 1999-06-04
20.

Stuart Little

5.0

The adventures of a heroic and debonair stalwart mouse named Stuart Little with human qualities, who faces some comic misadventures while searching for his lost bird friend and living with a human family as their child.

Starring: Michael J. Fox, Geena Davis, Hugh Laurie, Jonathan Lipnicki, Nathan Lane
Directed by: Rob Minkoff
Release date: 1999-12-17

Also check Best comedy movies of 1998.

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

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