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Top Comedy Movies of 1999 Online

Looking for the funniest comedy movies of 1999 online? We've compiled a list of the top comedies that will have you laughing out loud. From award-winning hits to hidden gems, these films bring humor and entertainment to your screen. Watch the best comedy movies of 1999 online and enjoy endless laughter anytime, anywhere.

The Big Kahuna (1999)

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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.

Detroit Rock City (1999)

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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!

Sex, Shame & Tears (1999)

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A comedic drama featuring two couples and two old friends in Mexico City. Tomas visits Carlos and Ana, while Miguel and Andrea are joined by Maria. The presence of guests triggers lust, rejection, infidelities, reconciliation and other consequences.

Jakob the Liar (1999)

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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.

Paul F. Tompkins: Driven to Drink (1999)

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In this (mostly) one-man show, comedian Paul F. Tompkins holds forth on alcohol, pretension and Hollywood, managing to drink four full pints of Guinness over the course of the performance.

Three Kings (1999)

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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.

Life (1999)

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

Two Hands (1999)

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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.

The Best Man (1999)

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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.

Topsy-Turvy (1999)

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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.

The One and Only (1999)

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When kitchen fitter Niller comes to install Sus's new suite, their immediate attraction to one another proves a sweet escape from both of their problematic relationships.

The Cup (1999)

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While the World Cup is being played in France, two young Tibetan refugees arrive at a monastery in India. The atmosphere of serene contemplation is soon disrupted by soccer fever, as the two students desperately seek a TV to watch the final.

American Pie (1999)

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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.

The Thirteenth Year (1999)

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A teen learns that his birth mother is a mermaid after he begins to grow fins and slimy scales on his thirteenth birthday.

Drive Me Crazy (1999)

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Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.

Mumford (1999)

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When a would-be psychologist, curiously named Dr. Mumford, comes to the idyllic town of the same name and offers his talent for listening and a disarming frankness, the town's quirkiest citizens scramble for a seat on his couch. As he lightens hearts darkened by old secrets no one realizes he's hiding a whopper of his own, or that he's fallen head over heels for one of his patients!

Don't Look Under the Bed (1999)

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A girl calls on her brother's imaginary friend to banish a mischievous boogeyman who has framed her for his pranks.

East Is East (1999)

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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.

Baadshah (1999)

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A small time detective is mistaken as a CBI agent and gets embroiled in a deadly mission to save the Chief Minister from an assassination attempt.

August 32nd on Earth (1999)

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After escaping unscathed from a car accident, photo model Simone decides that having a baby is the only way to give her vacant life some meaning. She asks her best friend Philippe to get her pregnant, and he reluctantly agrees, on the condition that they conceive somewhere in a desert, so they leave Montréal on a 24-hour round-trip to Salt Lake City to find a suitable spot.

Tumbleweeds (1999)

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Whenever trouble strikes in one of her relationships, single mother Mary Jo Walker and her daughter, Ava, pack up and move to another city, a routine Ava is tiring of. This time, they are helped on their move to San Diego by trucker Jack Ranson. While Ava settles in, getting a leading part in the school play, Jack starts dating Mary Jo but soon reveals himself to be controlling and aggressive. Mary Jo prepares to flee again, angering Ava.

Blue Streak (1999)

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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.

Analyze This (1999)

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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.

Big Daddy (1999)

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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.

The Other Sister (1999)

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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.

Tea with Mussolini (1999)

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In 1930s fascist Italy, adolescent Luca just lost his mother. His father, a callous businessman, sends him to be taken care of by British expatriate Mary Wallace. Mary and her cultured friends - including artist Arabella, young widow Elsa, and archaeologist Georgie - keep a watchful eye over the boy. But the women's cultivated lives take a dramatic turn when Allied forces declare war on Mussolini.

An Ideal Husband (1999)

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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.

A Midsummer Night's Dream (1999)

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The lovely Hermia is to wed Demetrius, but she truly cares for Lysander. Hermia's friend, Helena, is in love with Demetrius, while other romantic entanglements abound in the woods, with married fairy rulers Titania and Oberon toying with various lovers and each other.

Tower of Terror (1999)

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A disgraced reporter investigates an abandoned luxury hotel where five people mysteriously disappeared sixty years earlier.

The Breaks (1999)

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Derrick, a racially-confused Irishman raised in the hood by a black family is having the worst day ever. Determined to prove to his fed-up mother and would-be girlfriend that he's not a screw-up, he sets out to do one thing right (get some milk) and even that proves to be a challenge! Hilarious encounters with racist red-neck cops, local gangsters and 'flamboyant' pawn shop owners ensue, and along the way Derek shows that he can actually do things for others and maybe even get his own life together.

Drop Dead Gorgeous (1999)

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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.

Gorgeous (1999)

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When Ah Bu, a girl from a small fishing town in Taiwan, finds a glass bottle with a romantic message, she travels to Hong Kong to find her prince charming. As it turns out, her prince charming, Albert, happens to be gay. But all is not lost when Ah Bu meets the dashing Chi Wu. Meanwhile, Ah Bu's boyfriend from Taiwan comes looking for her, as the action and romance follow Ah Bu back to Taiwan.

Annie (1999)

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Things seem pretty bad for a young girl living a "hard-knock life" in an orphanage. Fed up with the dastardly Miss Hannigan, Annie escapes the run-down orphanage determined to find her mom and dad. It's an adventure that takes her from the cold, mean streets of New York to the warm, comforting arms of bighearted billionaire Oliver Warbucks - with plenty of mischief and music in between.

Cookie's Fortune (1999)

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

Hum Dil De Chuke Sanam (1999)

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A newly-wed man discovers that his wife is in love with another man and decides to unite them. Ignoring the ridicule he might have to face for this, he takes his wife to Italy in search of her love.

In Bed with Santa (1999)

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Sara invites her ex-husbands and their new families to celebrate Christmas with her and her husband Janne. Sara has always wanted to have a baby with Janne, and at the dinner table she reveals the news: she's pregnant. The only problem is that Janne had a vasectomy two years ago, without Sara knowing it. The secret starts to spread among the guests, and in no time everyone knows but Sara. The party heads for a complete disaster. Who's the real father?

She's All That (1999)

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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.

Kennedy et moi (1999)

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If he buys a gun, visits his wife's lover, and ends up savagely biting his dentist, Samuel Polaris is in bad shape. Very bad. Unless the others, the “normal” people – with their career plans, their adulteries, their arrogant incompetence – have fallen into a sort of collective madness. Who knows. Because he has no choice, because he is in love with his wife and because he refuses to resign himself to the worst, Samuel Polaris decides to regain his dignity. Even if, to do this, he has to steal from his psychiatrist the watch that Kennedy was wearing the day he was assassinated.

Jawbreaker (1999)

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When an exclusive clique of teenage socialites accidentally murder their best friend on the morning of her birthday, the three girls responsible conspire to hide the truth.

The Adventures of Elmo in Grouchland (1999)

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Elmo loves his fuzzy, well-worn blue blanket more than anything in the whole world. However, when Elmo's blanket gets sucked through a colorful, swirling tunnel into Grouchland, the yuckiest place on earth, Elmo goes on an adventure to Grouchland to retrieve his prized possession.

Austin Powers: The Spy Who Shagged Me (1999)

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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.

Mystery, Alaska (1999)

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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.

Thumb Wars: The Phantom Cuticle (1999)

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The hilarious story of a restless young farm-thumb, Loke Groundrunner, and his tasty companion, Princess Bunhead, who go on an quest to combat Black Helmet Man and the Evil Thumbpire.

Passport to Paris (1999)

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Sent to Paris to visit their grandfather, the twins fall in love with France, not to mention two French boys.

The Key to Sex (1999)

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When brainy office assistant Simon is left in charge of the boss's Hollywood mansion, the weekend becomes an opportunity of a lifetime. Entrusted by power-hungry movie producer Alan to guard the estate, Simon thinks he's finally made the grade until he learns that his friends and co-workers have their own plans for the place...

Bowfinger (1999)

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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.

Siam Sunset (1999)

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A British design executive, who seemingly has everything going for him has his life totally changed when a refrigerator falls from an aircraft and lands on his wife...

The Theory of Flight (1999)

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A dreamer who aspires to human flight is assigned public service after one of his attempts off a public building. This leads him to meeting a young woman, who is dying of motor neuron disease. The strong-willed woman admits her wish to be de-flowered before her death. The man, struggling to maintain his relationship with his girl friend, declines but offers to help pay for a gigolo to do the deed. The following events play off the inherent comedy and drama of the circumstances.

License to Live (1999)

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Yutaka was fourteen years old when he was run over by a car and fell into a coma. Now, ten years later, he wakes up and realizes that his family is not intact anymore: father, mother and sister live at different places. Yutaka decides to re-open the pony farm that his family once ran.

Love Stinks (1999)

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A movie about a relationship...that's worse than yours. Seth (Stewart), a sitcom writer-producer, meets Chelsea (Wilson), an interior decorator, at his best friend's (Bellamy) wedding. He's immediately sexually attracted to her while she's instantly attracted to his single-ness. They both ditch their wedding dates and start their own date that same night. The two become a couple, appearing very happy until after a couple of years of postponing a marriage proposal. When Chelsea realizes that Seth wants to remain single and together, she becomes quite bitter. In the next hour of the movie, the two engage in behavior that makes the War of the