Watch 1999 Movies Online in Canada
Explore the best 1999 movies in Canada. From box office hits to fan-favorite films, 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, 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.
Movie
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.
Cosy Dens (1999 )
Movie
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.
Herod's Law (1999 )
Movie
Molly McKay is a profoundly autistic twenty-something woman who has lived in an institution from a young age following her parents' death in a car accident. When the institution must close due budget cuts, Molly is left in the care of her neurotypical, older brother, Buck McKay, an advertising executive and perennial bachelor. Buck makes her undergo an experimental medical treatment, with unexpectedly drastic results.
Molly (1999 )
Movie
An English auctioneer proposes to the daughter of a mafia kingpin, only to realize that certain "favors" would be asked of him.
Mickey Blue Eyes (1999 )
Movie
Ben Holmes, a professional book-jacket blurbologist, is trying to get to Savannah for his wedding. He just barely catches the last plane, but a seagull flies into the engine as the plane is taking off. All later flights are cancelled because of an approaching hurricane, so he is forced to hitch a ride in a Geo Metro with an attractive but eccentric woman named Sara.
Forces of Nature (1999 )
Movie
The adventures of married couple Henry and Nancy Clark, vexed by misfortune while in New York City for Henry's job interview.
The Out-of-Towners (1999 )
Movie
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.
Two Hands (1999 )
Movie
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.
Kikujiro (1999 )
Movie
A romantic comedy about a mysterious love letter that turns a sleepy New England town upside down.
The Love Letter (1999 )
Movie
A memoir of the lives of a family growing up on a post World War I British estate headed up by a strong disciplinarian, her daughter, her inventor husband, their ten year old son and his older sister. Through the household comes a number of suitors hoping to impress the young woman, including an aviator. When the elder woman's son shows up at the estate with his French fiancé, everything gets thrown into turmoil. The young boy takes a sudden interest in her sexual allure and his father is disturbed by his own non-Victorian feelings.
My Life So Far (1999 )
Movie
In this coming-of-age comedy, Tim Dunphy is leading a go-nowhere existence, spending his days smoking pot and hanging out with his best friend, Drugs Delaney. But Tim's lazy days of getting high are jettisoned after a brush with the law convinces his blue-collar dad to send him to a Connecticut prep school. The one saving grace of the new school is Jane, a fellow student Tim falls for immediately.
Outside Providence (1999 )
Movie
Taped in July before a live audience at the Showbox Theatre in Seattle, Cross pushes his brash humor to new extremes, offering uncensored remarks on the Virgin Mary, trendy advertising, violence in the media, airports and pornography, Dr. Kevorkian, organ donations, High Times magazine and religious fundamentalists.
David Cross: The Pride Is Back (1999 )
Movie
In a virtually all-white Iowa town, Flip daydreams of being a hip-hop star, hanging with Snoop Doggy Dogg and Dr. Dre. He practices in front of a mirror and with his two pals, James and Trevor. He talks Black slang, he dresses Black. He's also a wannabe pusher, selling flour as cocaine. And while he talks about "keeping it real," he hardly notices real life around him: his father's been laid off, his mother uses Food Stamps, his girlfriend is pregnant, James may be psychotic, one of his friends (one of the town's few Black kids) is preparing for college, and, on a trip to Chicago to try to buy drugs, the cops shoot real bullets. What will it take for Flip to get real?
Whiteboyz (1999 )
Movie
A 1950s used-car salesman wants to make a low-budget film about a trucker who accidentally runs down a child.
The Woman Chaser (1999 )
Movie
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!
Mumford (1999 )
Movie
Chris Rock brings his critically acclaimed brand of social commentary-themed humour to this HBO Special, extolling his razor-sharp wit and wisdom on such topics as gun control, President Clinton, homophobia, racism, black leaders and relationships.
Chris Rock: Bigger & Blacker (1999 )
Movie
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.
Tumbleweeds (1999 )
Movie
Michael Winslow standup
Michael Winslow Live (1999 )
Movie
Pamela Drury is unhappy, and alone. On her birthday she stumbles across a photo of Robert Dickson, and wonders what would've happened had she said yes to his proposal. A freak accident causes Pamela to live out the life she could've had, but is the grass on the other side always greener?
Me Myself I (1999 )
Movie
Thinking he's competing in Los Angeles' hot Platinum Scissors contest, Scottish hairstylist Crawford leaves Glasgow with a film crew to capture the event. When he learns he's a mere audience member, Crawford must find a way to become the mane event.
The Big Tease (1999 )
Movie
"Good son" Franck returns to his hometown to do a trainee managerial internship in the Human Resources department of the factory where his anxious, taciturn father has worked for 23 years.
Human Resources (1999 )
Movie
A millionaire car salesman who runs the biggest dealership in Midland City, Dwayne Hoover is a celebrity, loved and trusted by everyone. Then one day, he wakes up and realizes that his life is a total mess! But between the headaches posed by his pill-popping wife, a mistress who won't leave him alone, and a cross-dressing sales manager, Dwayne has picked a bad week for a midlife crisis.
Breakfast of Champions (1999 )
Movie
Military doctor General Klenski is arrested in Stalin's Russia in 1953 during an anti-Semitic political campaign accused of being a participant in so-called "doctors' plot".
Khrustalyov, My Car! (1999 )
Movie
Hammaam lives with his big family in a crowded Egyptian alley. As he is jobless, he loses his girl to a rich suitor. He then decides to leave for Amsterdam where his uncle has immigrated long ago. As soon as he arrives he loses his money and passport and gets assaulted in an inn. Adriano the young Egyptian emigrant saves his neck and helps him find his uncle who dumps him. Hence, Hammaam stays with a group of young Arabs. After his tiring journey between failure and success he falls in love with a young lady who helps him fulfill his dream of buying a certain famous restaurant. As his business flourishes, he returns home to visit his family proud of his success.
Hammam Fe Amsterdam (1999 )
Movie
After her 27th birthday, Silvia Prieto decides to take charge of her life and make some changes. At the same time, she suddenly finds herself intertwined in the life of another woman who is also named Silvia Prieto.
Silvia Prieto (1999 )
Movie
A story told from three angles. Max meets Elizabeth; they live together, but when she talks of marriage, he balks. He becomes extremely jealous, probably without cause, and thinks she's taken up with a friend of his, Jack. Elizabeth, stung by Max's refusal to marry, catches Jack's eye, but the friendship seems innocent. Lena, who works with Max, likes him and realizes she can manipulate his jealousy and maybe engineer his split from Elizabeth. When she's sure Elizabeth is with a man, she calls Max at work, sending him home to confront the lovers. Then, Lena feels guilty and takes off for Max's apartment. What's really going on? Who's with Elizabeth?
Wishful Thinking (1999 )
Movie
Malabar Police is a 1999 Tamil comedy crime film directed by P. Vasu. The film features Sathyaraj, Kushboo, Abbas and Mumtaj in lead roles. The film, produced by Shanthi Vasudevan, had musical score by S. A. Rajkumar and was released on 6 August 1999. Despite negative reviews from the critics, the film turn out be a blockkbuster of the year.
Malabar Police (1999 )
Movie
Anja is a beautiful and very well proportioned high school senior... and still a virgin. She insists that she wants her first time to be with a guy, who knows what it's about. Her rich (and arrogant, pretentious and obnoxious) boyfriend Peter serves the purpose, and he's more than willing. In fact, he's pushing forward as much as he can, but Victor, a freshman who has a serious crush on Anja, has other plans. Her first time should definitely not be with this buffoon, and he's ready to take it VERY far!
Love at First Hiccough (1999 )
Movie
Every Friday, Abigail religiously consults Madame Lola, a fortune teller. The old shrewd lady takes advantage of Abigail’s extreme grip on superstition by giving her signs about the perfect man for her. Nelson also takes advantage on the situation and paid Madame Lola to give Abigail signs that would make her believe that he is the one for her. Eventually through Nelson’s perseverance, and Madame Lola’s bogus prediction, Abigail started to believe that Nelson is her Mr. Right. But there is no secret that remains uncover.
Hey Babe! (1999 )
Movie
Two lovers want to get married, but only with their parents' consent.
Jodi (1999 )
Movie
After a boy's parents decide to divorce, he creates a "support group" for all the kids from failed marriages in his school. When kids who's parents aren't divorced start to pick on them, they agree to cause their parents to divorce as well.
Operation Splitsville (1999 )
Movie
A featurette directed by French actress Edwige Shaki where Eric Rohmer worked as a technical adviser, THE CURVE is a movie that has the inimitable Rohmer stamp. Talky, it makes its fifteen minutes seem a little longer. However, it's a playful little thing, where an art student meets his grandfather, a sculptor, and both exchange ideas about that part of the woman that is so alluring -- the curve of her back.
The Curve (1999 )
