Best Comedy Movies of 1999

The highest-rated comedy films from 1999, ranked by MovieMagicScore based on authentic viewer ratings.

Comedy 1998 Comedy 2000 All Time Comedy

Action Drama Horror Science Fiction Thriller Romance Animation Documentary Fantasy Crime

Toy Story 2

1999

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.

7.6

10 Things I Hate About You

1999

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.

7.6

All About My Mother

1999

Following the tragic death of her teenage son, Manuela travels from Madrid to Barcelona in an attempt to contact the long-estranged father the boy never knew. She reunites with an old friend, an outspoken transgender sex worker, and befriends a troubled actress and a pregnant, HIV-positive nun.

7.6

Being John Malkovich

1999

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.

7.4

Office Space

1999

A depressed white-collar worker tries hypnotherapy, only to find himself in a perpetual state of devil-may-care bliss that prompts him to start living by his own rules, and hatch a hapless attempt to embezzle money from his soul-killing employers.

7.4

Tel chi el telùn

1999

A comedy show.

8.0

Notting Hill

1999

London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.

7.3

South Park: Bigger, Longer & Uncut

1999

In this feature film based on the hit animated series, the third graders of South Park sneak into an R-rated film by ultra-vulgar Canadian television personalities Terrance and Phillip, and emerge with expanded vocabularies that leave their parents and teachers scandalized. When outraged Americans try to censor the film, the controversy spirals into a call to wage war on Canada and Terrance and Phillip end up on death row, with the kids their only hope of rescue.

7.3

Kikujiro

1999

Brash, loudmouthed and opportunistic, Kikujiro is the unlikely companion for Masao who is determined to see the mother he has never met. The two begin a series of adventures which soon turns out to be a whimsical journey of laughter and tears with a wide array of surprises and unique characters along the way.

7.5

#10

Man on the Moon

1999

The story of the life and career of eccentric avant-garde comedian, Andy Kaufman.

7.2

#11

Herod's Law

1999

In the 1940s, a small Mexican town has seen its last three mayors assassinated in rapid succession. A naive janitor is recruited to become the new mayor, and he believes he will modernize the little town and usher in a reign of peace. But the system corrupts him very quickly, and he takes to abusing his power while associating with an unscrupulous assortment of opportunists, hypocrites and criminals.

7.9

#12

Scooby-Doo! and the Witch's Ghost

1999

Scooby-Doo and the Mystery Gang visit Oakhaven, Massachusetts to seek strange goings on involving a famous horror novelist and his ancestor who is rumored to have been a witch.

7.4

#13

Galaxy Quest

1999

For four years, the courageous crew of the NSEA Protector — Commander Peter Quincy Taggart, Lieutenant Tawny Madison, and Doctor Lazarus — set off on a thrilling and often dangerous mission in space ... until their series was cancelled! Now, twenty years later, aliens under attack have mistaken the Galaxy Quest television transmissions for "historical documents" and beam up the crew of has-been actors to save the universe. With no script, no director, and no clue, the actors must turn in the performances of their lives.

7.1

#14

American Movie

1999

American Movie documents the story of filmmaker Mark Borchardt, his mission, and his dream. Spanning over two years of intense struggle with his film, his family, financial decline, and spiritual crisis, American Movie is a portrayal of ambition, obsession, excess, and one man's quest for the American Dream.

7.6

#15

Mickey's Once Upon a Christmas

1999

Mickey, Minnie, and their famous friends Goofy, Donald, Daisy and Pluto gather together to reminisce about the love, magic and surprises in three wonder-filled stories of Christmas past.

7.1

#16

Bang, Boom, Bang

1999

Bank robber Kalle Grabowski escapes from prison while his unemployed smalltime crook buddy is sitting around doing nothing after he just lost all their money. A fast paced comedy from German director Peter Thorwarth.

7.5

#17

In China They Eat Dogs

1999

Arvid is an ordinary bank clerk who lives a rather unassuming life with his dear girlfriend. But his life is turned completely upside down when he bravely manages to avert a robbery against the bank where he works.

7.3

#18

Dogma

1999

An abortion clinic worker with a special heritage is called upon to save the existence of humanity from being negated by two renegade angels trying to exploit a loophole and reenter Heaven.

6.9

#19

King of Comedy

1999

Wan Tin-Sau is an actor who cannot seem to catch a break, since his only professional jobs are limited to being a movie extra. As well as being an actor, he is also the head of his village's community center.

7.4

#20

Cosy Dens

1999

Two families, Sebkovi and Krausovi, are celebrating Christmas, but not everyone is in a good mood. The teenage kids think that their fathers are totally stupid, and the fathers are sure that their children are nothing more than rebels, hating anything they say.

7.9

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Best Comedy Movies of 1999

This ranking features the top comedy movies released in 1999, sorted by MovieMagicScore viewer ratings. Looking for more? Browse all genres from 1999 or see the best comedy movies of all time.