Best Comedy Movies of 1999

1.

The Iron Giant

6.6
8.1/10 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.

Being John Malkovich

6.2
7.8/10 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
4.

Office Space

6.2
7.7/10 IMDB

Unable to endure another mind-numbing day at Initech Corporation, cubicle slave Peter Gibbons gets fired up and decides to get fired.

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
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.

Man on the Moon

6.1
7.4/10 IMDB

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

Starring: Jim Carrey, Courtney Love, Bob Zmuda, Danny DeVito, Gerry Becker, Leslie Lyles, Greyson Erik Pendry, George Shapiro, Vincent Schiavelli, Paul Giamatti ..
Directed by: Miloš Forman
Release date: 1999-12-22
7.

Notting Hill

6.1
7.2/10 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: 1999-05-21
8.

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
9.

Galaxy Quest

5.9
7.4/10 IMDB

For four years, the courageous crew of the NSEA protector - "Commander Peter Quincy Taggart" (Tim Allen), "Lt. Tawny Madison (Sigourney Weaver) and "Dr.Lazarus" (Alan Rickman) - set off on a thrilling and often dangerous mission in space...and then 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.

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
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
11.

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
12.

Three Kings

5.7
7.1/10 IMDB

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, Nora Dunn, Jamie Kennedy, Saïd Taghmaoui, Mykelti Williamson, Holt McCallany ..
Directed by: David O. Russell
Release date: 1999-04-21
13.

American Pie

5.6
7.0/10 IMDB

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, Tara Reid, Eddie Kaye Thomas, Seann William Scott, Eugene Levy, Natasha Lyonne ..
Directed by: Paul Weitz, Chris Weitz
Release date: 1999-07-09
14.

Analyze This

5.5
6.7/10 IMDB

Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family," unlucky shrink Dr. Ben Sobel is given just days to resolve Vitti's emotional crisis and turn him into a happy, well-adjusted gangster.

Starring: Robert De Niro, Billy Crystal, Lisa Kudrow, Chazz Palminteri, Joe Viterelli, Molly Shannon, Kyle Sabihy, Frank Pietrangolare, Ron Madoff, Leo Rossi ..
Directed by: Harold Ramis
Release date: 1999-03-05
15.

Austin Powers: The Spy Who Shagged Me

5.3
6.6/10 IMDB

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 to try to save the world in his own unbelievably groovy way.

Starring: Mike Myers, Heather Graham, Michael York, Robert Wagner, Rob Lowe, Seth Green, Mindy Sterling, Verne Troyer, Elizabeth Hurley, Gia Carides ..
Directed by: Jay Roach
Release date: 1999-06-08
16.

Big Daddy

5.3
6.4/10 IMDB

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, Leslie Mann, Allen Covert, Rob Schneider, Peter Dante, Steve Buscemi ..
Directed by: Dennis Dugan
Release date: 1999-06-25
17.

Blue Streak

5.3
6.3/10 IMDB

Miles Logan is a jewel thief who just hit the big time by stealing a huge diamond. However, after two years in jail, he comes to find out that he hid the diamond in a police building that was being built at the time of the robbery. In an attempt to regain his diamond, he poses as an LAPD detective.

Starring: Martin Lawrence, Luke Wilson, Dave Chappelle, Peter Greene, Nicole Ari Parker, William Forsythe, Graham Beckel, Robert Miranda, Olek Krupa, Saverio Guerra ..
Directed by: Les Mayfield
Release date: 1999-09-17
Best Comedy Movies of 1999 : Blackadder: Back & Forth
18.

Blackadder: Back & Forth

5.2
7.6/10 IMDB

What was a cunning plan from Lord Edmund Blackadder V to fake a time machine on his gullibly incompetent friends, turns out to be the real thing and hurls him and his imbecile underling, Baldrick, through the course of human history.

Starring: Rowan Atkinson, Tony Robinson, Stephen Fry, Hugh Laurie, Tim McInnerny, Miranda Richardson, Patsy Byrne, Colin Firth, Rik Mayall, Kate Moss ..
Directed by: Paul Weiland
Release date: 1999-03-29
19.

Go

5.2
7.2/10 IMDB

Grocery store clerk Simon occasionally sells drugs from his cash register at work, so when soap opera actors Adam and Zack come looking for Ecstasy on a quiet Christmas Eve, they are surprised to find Ronna covering his shift. Desperate for money, Ronna decides to become an impromptu drug dealer, unaware that Adam and Zack are secretly working for obsessed narcotics officer Burke.

Starring: Sarah Polley, Katie Holmes, Jay Mohr, Timothy Olyphant, William Fichtner, Scott Wolf, Robert Peters, Suzanne Krull, Desmond Askew, Nathan Bexton ..
Directed by: Doug Liman
Release date: 1999-04-09
20.

Human Traffic

5.1
7.1/10 IMDB

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

Starring: John Simm, Shaun Parkes, Nicola Reynolds, Lorraine Pilkington, Danny Dyer, Dean Davies, Andrew Lincoln, Terence Beesley, Jo Brand, Richard Coyle ..
Directed by: Justin Kerrigan
Release date: 1999-06-04
21.

Stuart Little

5.1
6.0/10 IMDB

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, Jeffrey Jones, Connie Ray, Allyce Beasley, Brian Doyle-Murray, Estelle Getty ..
Directed by: Rob Minkoff
Release date: 1999-12-17
22.

Election

5.1
7.3/10 IMDB

Jim McAllister, a well-liked high school government teacher, can't help but notice that successful student Tracy Flick uses less than ethical tactics to get what she wants. When Tracy runs for school president, Jim feels that she will be a poor influence on the student body and convinces Paul, a dim-witted but popular student athlete, to run against Tracy. When she becomes aware of Jim's secret involvement in the race, a bitter feud is sparked.

Starring: Matthew Broderick, Reese Witherspoon, Chris Klein, Jessica Campbell, Mark Harelik, Phil Reeves, Molly Hagan, Delaney Driscoll, Colleen Camp, Frankie Ingrassia ..
Directed by: Alexander Payne
Release date: 1999-04-23
23.

Sweet and Lowdown

5.1
7.2/10 IMDB

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: Woody Allen, Ben Duncan (DJ), Daniel Okrent, Dan Moran, Tony Darrow, Chris Bauer, Sean Penn, Darryl Alan Reed, James Urbaniak, Uma Thurman ..
Directed by: Woody Allen
Release date: 1999-12-03
24.

Topsy-Turvy

5.0
7.3/10 IMDB

After their production "Princess Ida" meets with less-than-stunning reviews, the relationship between Gilbert and Sullivan is strained to breaking. Their friends and associates attempt to get the two to work together again, which opens the way to "The Mikado," one of the duo's greatest successes.

Starring: Allan Corduner, Jim Broadbent, Timothy Spall, Dexter Fletcher, Shirley Henderson, Lesley Manville, Ron Cook, Andy Serkis, Wendy Nottingham, Kevin McKidd ..
Directed by: Mike Leigh
Release date: 1999-12-15
25.

She's All That

5.0
5.9/10 IMDB

High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.

Starring: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Jodi Lyn O'Keefe, Anna Paquin, Clea DuVall, Kieran Culkin, Kevin Pollak, Lil' Kim ..
Directed by: Robert Iscove
Release date: 1999-01-29
26.

Never Been Kissed

5.0
6.0/10 IMDB

Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.

Starring: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon, Jenny Bicks, Jessica Alba, John C. Reilly, James Franco, Octavia Spencer, Garry Marshall ..
Directed by: Raja Gosnell
Release date: 1999-04-09
27.

Life

5.0
6.7/10 IMDB

Two men in 1930s Mississippi become friends after being sentenced to life in prison together for a crime they did not commit.

Starring: Eddie Murphy, Martin Lawrence, Obba Babatundé, Nick Cassavetes, Bernie Mac, Michael Taliferro, Anthony Anderson, Barry Shabaka Henley, Miguel A. Núñez, Jr., Bokeem Woodbine ..
Directed by: Ted Demme
Release date: 1999-04-16
28.

East Is East

4.9
6.9/10 IMDB

In 1971 Salford fish-and-chip shop owner George Khan expects his family to follow his strict Pakistani Muslim ways. But his children, with an English mother and having been born and brought up in Britain, increasingly see themselves as British and start to reject their father's rules on dress, food, religion, and living in general.

Starring: Om Puri, Linda Bassett, Ian Aspinall, Jimi Mistry, Archie Panjabi, Jordan Routledge, Chris Bisson, Lesley Nicol, Emil Marwa, Raji James ..
Directed by: Damien O'Donnell
Release date: 1999-05-14
29.

Detroit Rock City

4.9
6.8/10 IMDB

In 1978, a Kiss concert was an epoch-making event. For the three teen fans in Detroit Rock City getting tickets to the sold-out show becomes the focal point of their existence. They'll do anything for tickets -- compete in a strip club's amateur-night contest, take on religious protesters, even rob a convenience store!

Starring: Giuseppe Andrews, James DeBello, Edward Furlong, Sam Huntington, Lin Shaye, Melanie Lynskey, Natasha Lyonne, Shannon Tweed, Emmanuelle Chriqui, Kristin Booth ..
Directed by: Adam Rifkin
Release date: 1999-08-13
30.

Two Hands

4.9
7.0/10 IMDB

A 19-year-old finds himself in debt to a local gangster when some gang loot disappears and sets him on the run from thugs. Meanwhile, two street kids start a shopping spree when they find the missing money.

Starring: Heath Ledger, Bryan Brown, Rose Byrne, David Field, Tom Long, Tony Forrow, Steven Vidler, Dale Kalnins, Kiri Paramore, William Drury ..
Directed by: Gregor Jordan
Release date: 1999-07-29
31.

Ravenous

4.9
6.9/10 IMDB

Upon receiving reports of missing persons at Fort Spencer, a remote Army outpost on the Western frontier, Capt. John Boyd investigates. After arriving at his new post, Boyd and his regiment aid a wounded frontiersman who recounts a horrifying tale of a wagon train murdered by its supposed guide -- a vicious U.S. Army colonel gone rogue. Fearing the worst, the regiment heads out into the wilderness to verify the gruesome claims.

Starring: Guy Pearce, Robert Carlyle, David Arquette, Jeremy Davies, Neal McDonough, Stephen Spinella, Joseph Runningfox, Bill Brochtrup, Sheila Tousey, Jeffrey Jones ..
Directed by: Antonia Bird
Release date: 1999-03-16
32.

Blast from the Past

4.9
6.7/10 IMDB

Following a bomb scare in the 1960s that locked the Webers into their bomb shelter for 35 years, Adam now ventures forth into Los Angeles to obtain food and supplies for his family, and a non-mutant wife for himself.

Starring: Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek, Nathan Fillion, Dave Foley, Joey Slotnick, Mary Ann Hermansen, Deborah Kellner, Don Yesso ..
Directed by: Hugh Wilson
Release date: 1999-02-12
33.

The Big Kahuna

4.9
6.6/10 IMDB

Three salesmen working for a firm that makes industrial lubricants are waiting in the company's "hospitality suite" at a manufacturers' convention for a "big kahuna" named Dick Fuller to show up, in hopes they can persuade him to place an order that could salvage the company's flagging sales.

Starring: Kevin Spacey, Danny DeVito, Peter Facinelli, Paul Dawson, Christopher Donahue, Ron Komora, Frank L. Messina, George F. Miller ..
Directed by: John Swanbeck
Release date: 1999-11-17
34.

Runaway Bride

4.9
5.5/10 IMDB

Ike Graham, New York columnist, writes his text always at the last minute. This time, a drunken man in his favourite bar tells Ike about Maggie Carpenter, a woman who always flees from her grooms in the last possible moment. Ike, who does not have the best opinion about females anyway, writes an offensive column without researching the subject thoroughly.

Starring: Julia Roberts, Richard Gere, Joan Cusack, Rita Wilson, Hector Elizondo, Christopher Meloni, Paul Dooley, Donal Logue, Sela Ward, Sandra Taylor ..
Directed by: Garry Marshall
Release date: 1999-07-30
35.

Cookie's Fortune

4.9
6.8/10 IMDB

Conflict arises in the small town of Holly Springs when an old woman's death causes a variety of reactions among family and friends.

Starring: Glenn Close, Julianne Moore, Liv Tyler, Patricia Neal, Chris O'Donnell, Charles S. Dutton, Ned Beatty, Courtney B. Vance, Donald Moffat, Danny Darst ..
Directed by: Robert Altman
Release date: 1999-03-24
36.

The Best Man

4.9
6.7/10 IMDB

After writing a soon-to-be bestselling novel, writer and committed bachelor Harper attempts to hide the fact that his saucy new book is loosely based on the lives and loves of his tight-knit group of friends. Harper is set to be best man at his friend Lance's wedding, and all his friends will be in attendance. When an advance copy of the book makes its way into the hands of his ex-flame, Jordan, Harper attempts to keep it under wraps.

Starring: Nia Long, Morris Chestnut, Harold Perrineau, Terrence Howard, Sanaa Lathan, Taye Diggs, Regina Hall, Monica Calhoun, Jim Moody, Malcolm D. Lee ..
Directed by: Malcolm D. Lee
Release date: 1999-10-22
37.

Tea with Mussolini

4.9
6.9/10 IMDB

Semi-autobiographical film directed by Franco Zeffirelli, telling the story of young Italian boy Luca's upbringing by a circle of English and American women, before and during World War II.

Starring: Cher, Judi Dench, Joan Plowright, Maggie Smith, Lily Tomlin, Baird Wallace, Charlie Lucas, Massimo Ghini, Paolo Seganti, Claudio Spadaro ..
Directed by: Franco Zeffirelli
Release date: 1999-03-25
38.

An Ideal Husband

4.8
6.8/10 IMDB

Sir Robert Chiltern is a successful government minister, well-off and with a loving wife. All this is threatened when Mrs Cheveley appears in London with damning evidence of a past misdeed. Sir Robert turns for help to his friend Lord Goring, an apparently idle philanderer and the despair of his father. Goring knows the lady of old, and, for him, takes the whole thing pretty seriously.

Starring: Cate Blanchett, Minnie Driver, Rupert Everett, Julianne Moore, Jeremy Northam, Peter Vaughan, Ben Pullen, Marsha Fitzalan, Lindsay Duncan, John Wood ..
Directed by: Oliver Parker
Release date: 1999-04-15
39.

Drop Dead Gorgeous

4.8
6.6/10 IMDB

In a small Minnesota town, the annual beauty pageant is being covered by a TV crew. Former winner Gladys Leeman wants to make sure her daughter follows in her footsteps; explosions, falling lights, and trailer fires prove that. As the Leemans are the richest family in town, the police are pretty relaxed about it all. Despite everything, main rival (but sweet) Amber Atkins won't give up without a fight.

Starring: Kirsten Dunst, Ellen Barkin, Denise Richards, Amy Adams, Kirstie Alley, Allison Janney, Brittany Murphy, Sam McMurray, Mindy Sterling, Alexandra Holden ..
Directed by: Michael Patrick Jann
Release date: 1999-07-23
40.

Deuce Bigalow: Male Gigolo

4.8
5.7/10 IMDB

Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer is hot on his trail.

Starring: Rob Schneider, William Forsythe, Eddie Griffin, Arija Bareikis, Oded Fehr, Gail O'Grady, Richard Riehle, Jacqueline Obradors, Big Boy, Amy Poehler ..
Directed by: Mike Mitchell
Release date: 1999-12-10
41.

Bowfinger

4.8
6.5/10 IMDB

On the verge of bankruptcy and desperate for his big break, aspiring filmmaker Bobby Bowfinger concocts a crazy plan to make his ultimate dream movie. Rallying a ragtag team that includes a starry-eyed ingenue, a has-been diva and a film studio gofer, he sets out to shoot a blockbuster featuring the biggest star in Hollywood, Kit Ramsey -- only without letting Ramsey know he's in the picture.

Starring: Steve Martin, Eddie Murphy, Heather Graham, Christine Baranski, Jamie Kennedy, Adam Alexi-Malle, Kohl Sudduth, Barry Newman, Terence Stamp, Robert Downey Jr. ..
Directed by: Frank Oz
Release date: 1999-08-12
42.

Jakob the Liar

4.8
6.5/10 IMDB

In 1944 Poland, a Jewish shop keeper named Jakob is summoned to ghetto headquarters after being caught out after curfew. While waiting for the German Kommondant, Jakob overhears a German radio broadcast about Russian troop movements. Returned to the ghetto, the shopkeeper shares his information with a friend and then rumors fly that there is a secret radio within the ghetto.

Starring: Robin Williams, Armin Mueller-Stahl, Hannah Taylor-Gordon, Éva Igó, István Bálint, Justus von Dohnányi, Kathleen Gati, Bob Balaban, Alan Arkin, Michael Jeter ..
Directed by: Peter Kassovitz
Release date: 1999-09-16
43.

Mystery, Alaska

4.7
6.7/10 IMDB

In Mystery, Alaska, life revolves around the legendary Saturday hockey game at the local pond. But everything changes when the hometown team unexpectedly gets booked in an exhibition match against the New York Rangers. When quirky small-towners, slick promoters and millionaire athletes come together.

Starring: Russell Crowe, Hank Azaria, Mary McCormack, Burt Reynolds, Colm Meaney, Lolita Davidovich, Maury Chaykin, Ron Eldard, Ryan Northcott, Michael Buie ..
Directed by: Jay Roach
Release date: 1999-10-01
44.

A Midsummer Night's Dream

4.7
6.4/10 IMDB

A film adaptation of Shakespeare's comedy about lovers whose romantic affections are manipulated by fairy magic. The setting is updated to a Tuscan hill town in the late 19th century.

Starring: Rupert Everett, Calista Flockhart, Kevin Kline, Michelle Pfeiffer, Stanley Tucci, Christian Bale, Sophie Marceau, David Strathairn, Anna Friel, Dominic West ..
Directed by: Michael Hoffman
Release date: 1999-05-14
45.

Flawless

4.6
6.4/10 IMDB

An ultraconservative police officer suffers a debilitating stroke and is assigned to a rehabilitative program that includes singing lessons - with the drag queen next door.

Starring: Robert De Niro, Philip Seymour Hoffman, Barry Miller, Chris Bauer, Skipp Sudduth, Wilson Jermaine Heredia, Rory Cochrane, Daphne Rubin-Vega, Vincent Laresca, Karina Arroyave ..
Directed by: Joel Schumacher
Release date: 1999-11-26
46.

Varsity Blues

4.6
6.5/10 IMDB

In small-town Texas, high school football is a religion, 17-year-old schoolboys carry the hopes of an entire community onto the gridiron every Friday night. When star quarterback Lance Harbor suffers an injury, the Coyotes are forced to regroup under the questionable leadership of John Moxon, a second-string quarterback with a slightly irreverent approach to the game.

Starring: James Van Der Beek, Amy Smart, Jon Voight, Paul Walker, Ron Lester, Scott Caan, Ali Larter, Richard Lineback, Thomas F. Duffy, Joe Pichler ..
Directed by: Brian Robbins
Release date: 1999-01-15
Best Comedy Movies of 1999 : The Other Sister
47.

The Other Sister

4.6
6.4/10 IMDB

A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.

Starring: Juliette Lewis, Diane Keaton, Tom Skerritt, Giovanni Ribisi, Poppy Montgomery, Sarah Paulson, Linda Thorson, Joe Flanigan, Juliet Mills, Tracy Reiner ..
Directed by: Garry Marshall
Release date: 1999-02-26
48.

Scooby-Doo! and the Witch's Ghost

4.5
7.2/10 IMDB

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 be a witch.

Starring: Scott Innes, Mary Kay Bergman, Frank Welker, B.J. Ward, Kimberly Brooks, Jennifer Hale, Jane Wiedlin, Tim Curry, Bob Joles, Tress MacNeille ..
Directed by: Jim Stenstrum
Release date: 1999-11-05
49.

Idle Hands

4.5
6.2/10 IMDB

Anton is a cheerful but exceedingly non-ambitious 17-year-old stoner who lives to stay buzzed, watch TV, and moon over Molly, the beautiful girl who lives next door. However, it turns out that the old cliché about idle hands being the devil's playground has a kernel of truth after all.

Starring: Devon Sawa, Seth Green, Jessica Alba, Vivica A. Fox, Christopher Hart, Jack Noseworthy, Katie Wright, Sean Whalen, Nicholas Sadler, Elden Henson ..
Directed by: Rodman Flender
Release date: 1999-04-30
50.

Muppets from Space

4.5
6.2/10 IMDB

When Gonzo's breakfast cereal tells him that he's the descendant of aliens from another planet, his attempts at extraterrestrial communication get him kidnapped by a secret government agency, prompting the Muppets to spring into action. It's hard to believe Gonzo's story at first, but Kermit and friends soon find themselves on an epic journey into outer space filled with plenty of intergalactic misadventures.

Starring: Steve Whitmire, Dave Goelz, Bill Barretta, Frank Oz, Jerry Nelson, Jeffrey Tambor, F. Murray Abraham, Rob Schneider, Kathy Griffin, Josh Charles ..
Directed by: Tim Hill
Release date: 1999-07-14

Also check Best comedy movies of 2000.

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