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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A story of WWI soldiers and the Black struggle for pride and freedom. Eye witness testimonies of surviving veterans, official documents and archive photos reveal the incredible story of the British West Indies Regiment.
Mutiny (1999 )
Movie
On his death bed in the 1820s, King Ferdinando I of Naples tries to escape the ghosts of his bloody kingship by remembering his younger days, when he was allowed to go hunting and have fun, and inventing love games. Then he was obliged to marry Mary Caroline of Austria, daughter of Empress Mary Theresa, in a political marriage: unexpectedly, they became happy lovers, until court power games divided them, and a different historical season arrived.
Ferdinando and Carolina (1999 )
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Traces the Beats from Allen Ginsberg and Jack Kerouac's meeting in 1944 at Columbia University to the deaths of Ginsberg and William S. Burroughs in 1997. Three actors provide dramatic interpretations of the work of these three writers, and the film chronicles their friendships, their arrival into American consciousness, their travels, frequent parodies, Kerouac's death, and Ginsberg's politicization. Their movement connects with bebop, John Cage's music, abstract expressionism, and living theater. In recent interviews, Ginsberg, Burroughs, Kesey, Ferlinghetti, Mailer, Jerry Garcia, Tom Hayden, Gary Snyder, Ed Sanders, and others measure the Beats' meaning and impact.
The Source (1999 )
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This sequel to "Before Stonewall" documents the history of gay and lesbian life from the riots at Stonewall in 1969 to the present. Narrated by Melissa Etheridge, the film explains the work, struggles, victories, and defeats the gay community has weathered to become a vibrant and integral part of North American society.
After Stonewall (1999 )
Movie
Chaco Canyon, located in northwest New Mexico, is perhaps the only site in the world constructed in an elaborate pattern that mirrors the yearly cycle of the sun and the 19-year cycle of the moon. How did an ancient civilization, with no known written language, arrange its buildings into a virtual celestial calendar, spanning an area roughly the size of Ireland?
The Mystery of Chaco Canyon (1999 )
Movie
Tells the story of Sadie and Bessie Delany, two African-American (they preferred "colored") sisters who both lived past the age of 100. They grew up on a North Carolina college campus, the daughters of the first African-American Episcopal bishop, who was born a slave, and a woman with an inter-racial background. With the support of each other and their family, they survived encounters with racism and sexism in their own different ways. Sadie quietly and sweetly broke barriers to become the first African-American home-ec teacher in New York City, while Bessie, with her own brand of outspokenness, became the second African-American dentist in New York City. At the ages of 103 and 101, they told their story to Amy Hill Hearth, a white New York Times reporter who published an article about them. The overwhelming response launched a bestselling book, a Broadway play, and this film.
Having Our Say: The Delany Sisters' First 100 Years (1999 )
Movie
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.
Office Space (1999 )
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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.
10 Things I Hate About You (1999 )
Movie
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.
Notting Hill (1999 )
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When spirited young woman, Fanny Price is sent away to live on the great country estate of her rich cousins, she's meant to learn the ways of proper society. But while Fanny learns 'their' ways, she also enlightens them with a wit and sparkle all her own.
Mansfield Park (1999 )
Movie
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.
Blast from the Past (1999 )
Movie
Tracy Flick is running unopposed for this year’s high school student election. But Jim McAllister has a different plan. Partly to establish a more democratic election, and partly to satisfy some deep personal anger toward Tracy, Jim talks football player Paul Metzler to run for president as well.
Election (1999 )
Movie
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.
Being John Malkovich (1999 )
Movie
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.
American Pie (1999 )
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Privileged teenage friends Jenny, Nell and Stream spend their senior year on a quest to rid Stream of her virginity. However, Stream wants more than just her first sexual experience. She wants to have an orgasm -- but achieving this proves problematic, as the boys she meets are hardly sensitive enough to provide her the release she seeks. When it becomes clear that Nell and Jenny have never experienced an orgasm either, all three set out to get one.
Coming Soon (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.
Jawbreaker (1999 )
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The story of the life and career of eccentric avant-garde comedian, Andy Kaufman.
Man on the Moon (1999 )
Movie
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.
Big Daddy (1999 )
Movie
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.
Go (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.
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 )
Movie
Video store clerk Ed agrees to have his life filmed by a camera crew for a tv network.
EDtv (1999 )
Movie
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.
Bowfinger (1999 )
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Having already left three grooms at the altar, Maggie Carpenter is branded "the runaway bride" by jaded New York journalist Ike Graham. But, after his facts are called into question, Ike races to Maggie's hometown to save his reputation and report on her upcoming fourth trip down the aisle – during which he's convinced she'll run again. Though he's there on a muckraking mission, Ike can't help but fall for this breathtaking heartbreaker.
Runaway Bride (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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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.
Never Been Kissed (1999 )
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The portrait of a man and his attempts to make things up with life after losing his job.
Crane World (1999 )
Movie
Sent to Paris to visit their grandfather, the twins fall in love with France, not to mention two French boys.
Passport to Paris (1999 )
Movie
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.
Deuce Bigalow: Male Gigolo (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 )