Watch 1999 Movies and TV Shows Online in Canada
Explore the best 1999 movies and tv shows in Canada. From box office hits to fan-favorite films and series, discover top-rated titles, trending picks, and hidden gems that made 1999 a standout year for entertainment.
Take a trip back to 1999 and relive the best in entertainment in Canada. Browse a wide variety of movies and tv shows, including award-winning blockbusters, trending releases, and critically acclaimed favorites. Whether you're looking for action-packed thrillers, heartwarming dramas, laugh-out-loud comedies, or captivating documentaries, 1999 delivered something for everyone. Use Popcorn Time to easily find titles by genre, popularity, or release date, and rediscover the magic of 1999.
From the big screen to small-screen hits, explore the year's most memorable releases and create your own playlist of 1999's greatest entertainment. Start streaming now and see why 1999 remains a favorite among movie and TV lovers.
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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.
She's All That (1999 )
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A neurotic L.A. building contractor pushes his reluctant wife into having a threesome. Unfortunately for him, his wife gets more out of it than he does and begins seducing every female she meets, including the contractor's secretary.
The Sex Monster (1999 )
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What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.
Held Up (1999 )
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A womanizing New York adman attempts to identify the causes of, and find a remedy for, his so-called addiction to sex, in order to win the love of a woman he respects.
Giving It Up (1999 )
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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.
Flawless (1999 )
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Oscar and Peter land a career-making opportunity when a Chicago tycoon chooses them to compete for the design of a cultural center. The tycoon mistakenly believes that Oscar is gay and has him spy on his mistress Amy. Oscar goes along with it and ends up falling in love with Amy.
Three to Tango (1999 )
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Todd Boomer is a college student aspiring to get into University. His chances are looking poor when his maths teacher, fails him in every maths test. Help arrives in the guise of the gorgeous Vicki, a mathematical genius who decides to tutor Todd. As the relationship develops,Todd finds himself in an affair with Vicki unknowing of her marriage to his math teacher.
My Teacher's Wife (1999 )
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Legendary comic Carlin comes back to the Beacon theater to angrily rant about airport security, germs, cigars, angels, children and parents, men, names, religion, god, advertising, Bill Jeff and minorities.
George Carlin: You Are All Diseased (1999 )
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Oh no! It appears as if Satan isn't going to fill his soul quota this month! So of course, he turns himself into a tour guide and takes a bus-load of unsuspecting tourists on a ride down the highway to hell.
Fatty Drives the Bus (1999 )
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After her mother's death, mediocre chef Amanda Shelton is having trouble attracting customers to her family's restaurant. While shopping for ingredients, she is given a magical crab by mysterious Gene O'Reilly. Afterward, Amanda's dishes suddenly become excellent, inducing strong emotional reactions in everyone who eats them. Tom Bartlett, who is preparing to open his own eatery, tries her cooking and falls in love.
Simply Irresistible (1999 )
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A slice-of-life story unfolds inside The Florentine, a bar in a Pennsylvania steel town whose brightest days are behind it, leaving behind many of life's disillusioned "losers." Its owner, Whitey (Michael Madsen), is deep in debt to the town's loan shark, Joe McCollough (Burt Young), and desperate for a path forward which won't cost him the bar. His sister, Molly (Virginia Madsen), is days away from her long-awaited nuptials, and then her former fiancé, Teddy (Tom Sizemore), shows up in town for the first time since leaving her at the altar years before. Ne'er-do-well Billy Belasco (Jim Belushi) runs a con on Frankie (Luke Perry) to steal the money for the wedding caterer, while long-time regular Bobby (Chris Penn) becomes a patron-cum-inhabitant as he hides from his fast-crumbling marriage to Vikki (Mary Stuart Masterson). Every plot in this multi-layered story seems to be at its nadir just as a pair of unlikely heroes emerge out of the backdrop to turn everything around.
The Florentine (1999 )
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Police investigate when a man having an affair with his brother's wife disappears suddenly.
Goodbye Lover (1999 )
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Executive transvestite Eddie Izzard takes her show to San Francisco to give a brief history of pagan and Christian religions, the building of Stonehenge, the birth of the Church of England and of Western empires, and the need for a European dream.
Eddie Izzard: Dress to Kill (1999 )
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Entropy is a semi-autobiographical film which tells the story of a young director struggling to make a film for a despotic studio while his life falls apart around him. Along the way, he goes on tour with U2 to help them make a music video, gets married in Vegas, and has a conversation with his cat.
Entropy (1999 )
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Norman Reedus stars as Harry Odum, a henpecked, 18-year-old momma's boy in Youngstown, Ohio, who -- with his violent temper -- impresses a local boss of the Jewish Mafia. Soon he's found his calling as a hit man alongside his crack addict partner Arnie Finklestein (Adrien Brody), and he discovers that his rage and complicated psychosis fuel his murderous abilities. Harry also falls for the organization's limping, Hungarian-born maid Iris (Elina Lowensohn), a romance complicated by Harry's Oedipal, sexual relationship with his domineering mother Kate (Deborah Harry).
Six Ways to Sunday (1999 )
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In order to impress his beautiful French neighbor, Dylan Ramsey dognaps her pet pooch so he can return him and become a hero.
Lost & Found (1999 )
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Bob, a sympathetic young man, keeps telling women what they want to hear to have a good time. Just as he is about to marry the daughter of a very wealthy banker, her father does a little research on his future son-in-law and finds out the truth about Bob. He forces Bob to marry his daughter and behave like the perfect husband, or else... Unfortunately, Bob meets "The One" just a few days before the wedding and had also told her what she wanted to hear, all of this unbeknownst to his future wife. Then right as he's trying to extricate himself from those dilemmas, two very protective Turkish brothers of one of his past affairs are after him to take revenge for taking her virginity!
All About Bob (1999 )
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Harry Sterndale, a failed photographer, is given a diagnosis of cancer and told that he has only three months to live. After thinking things over, he decides that since he is dying anyway, he will kill or destroy all the people that ever crossed or hurt him during his life - after all, he will be dead anyway long before he can come to trial and get his just desserts from society. Harry hires an assassin to finish himself off in style, and even has time to fall in love with Jill. However, there's just one small problem with Harry's master plan - the cancer diagnosis is totally inaccurate and now he's got a hitman on his trail and several policemen wanting to talk to him about some murders...
Parting Shots (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.
The Best Man (1999 )
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A radio-show assistant meets a budding screenwriter during a group-therapy session for sex addicts.
Between Your Legs (1999 )
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An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.
L.A. Without a Map (1999 )
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Dort, wo unsere Geschichte spielt, wissen nur die Hühner, was Stress bedeutet. Ansonsten geht es auf dem Lande ruhig zu, und so ist es kein Wunder, dass die jährliche “Hengst-Auktion” den Höhepunkt des kulturellen Lebens bildet – eine Veranstaltung, bei der die meistbietenden Damen ein Rendezvous mit den ansehnlichsten Jungbauern ersteigern können.
Das Gelbe vom Ei (1999 )
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When an eight year old girl loses her mother to cancer, her mother's last wish is for her to fall in love and find that special magical person. Twenty years later, she is alone, fired, and broke. When she and a friend decide to relocate to LA to start anew, she becomes attracted to their bus driver. Her friend, however, thinks she should go for someone more secure and established. The question arises: does one marry for love or money?
Follow Your Heart (1999 )
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A gifted teenager, dreaming of life beyond her small town, becomes inspired when a 15-year-old girl from New York moves in next door.
New Waterford Girl (1999 )
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Four young men fall in love with the same woman. When they all find themselves attracted by Kimberly, hey vow not to fight for her affections during the season -- but then she gets pregnant and doesn't know which teammate is the father.
Kimberly (1999 )
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An academic obsessed with "roadside attractions" and his tv-star daughter finally discover the world's largest ice cream cone, the centerpiece for an old gold-rush town struggling to stay on the map. They end up staying longer than expected because of an accident that spilled an unknown cola ingredient all over the highway. They spend the next few days with the various residents of the town which include a teenage girl who loves to blow things up and a boy trying to keep alive his fathers dream of building a beachside resort in the middle of the desert.
Desert Blue (1999 )
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Sheltered rich girl Charlene has an over-protective mother who insists that her daughter should marry a rich doctor. After Charlene's psychic predicts that her future lover is named Steven, she heads to L.A. to search for him.
Goosed (1999 )
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For fans of comedy, Sam Kinison needs no introduction. His scathing comedy tackled tough topics no other comedian dared to touch. Fed up and disenfranchised with his career as a Pentacostal preacher, Sam left the ministry to try his hand at comedy. Almost immediately, and thanks in part to the foresight of Rodney Dangerfield who showcased Sam on an HBO special, his piercing scream, extreme humor and irreverent take on life attracted attention. Containing rare, early footage of Sam preaching and performing stand up at the world famous Comedy Store, the Award Winning "Why Did We Laugh" tells the story of a comedic genius who touched a deeper chord in people than most entertainers. Sadly, Sam was taken from us far too early, yet leaving us with a lasting and unique legacy.
Sam Kinison: Why Did We Laugh? (1999 )
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Not long after moving into her own place, Maggie finds herself with two unsolicited roommates: her recently divorced mother, Lila, and her young brother. The timing is especially bad, considering Maggie has fallen hard for an attractive woman, Kim, only hours before they move in. What could be a nonissue becomes increasingly complicated -- since Maggie's family is unaware of her sexual orientation, and Maggie is not open to sharing that information.
Better Than Chocolate (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.
The Other Sister (1999 )
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Bah! Humbug! Susan Stone is definitely what you'd call a modern-day scrooge. She is a young, jaded book editor who is consumed with self-doubt and has lost the passion and drive that defined her childhood persona. On the verge of losing her job and being completely on the "outs" with her family, Susan has nearly given up on happiness. Out of nowhere, a cheerful, carefree seven-year-old girl named Suzie awaits Susan back at her apartment. It turns out that little Suzie is the embodiment of Susan's inner child, she is Susan as she once was years ago. Suzie has come to help the adult Susan rediscover and recapture the love of life that she's lost.
If You Believe (1999 )
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In this film within a film, a Belgian serial killer escapes prison and finds that a filmmaker is making a movie about his life. A maverick director, a merciless producer, an insubordinate star, and a conviced serial killer all try to survive the deadliest place on Earth: a movie set.
Shades (1999 )
