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
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 )
Movie
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 )
Movie
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.
Analyze This (1999 )
Movie
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.
August 32nd on Earth (1999 )
Movie
Orphan Mary Katherine Gallagher, an ugly duckling at St. Monica High School, has a dream: to be kissed soulfully. She decides she can realize this dream if she becomes a superstar, so her prayers, her fantasies and her conversations with her only friend focus on achieving super-stardom.
Superstar (1999 )
Movie
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.
A Midsummer Night's Dream (1999 )
Movie
Two men in 1930s Mississippi become friends after being sentenced to life in prison together for a crime they did not commit.
Life (1999 )
Movie
Single mother Adele August is bad with money, and even worse when it comes to making decisions. Her straight-laced daughter, Ann, is a successful high school student with Ivy League aspirations. When Adele decides to pack up and move the two of them from the Midwest to Beverly Hills, Calif., to pursue her dreams of Hollywood success, Ann grows frustrated with her mother's irresponsible and impulsive ways.
Anywhere but Here (1999 )
Movie
Jimmie is seeing his single friends get married one by one. He isn't too worried until his girlfriend Anne catches the bouquet at his friend Marco's wedding. Suddenly, his wild mustang days are numbered. He finally decides to propose to her, but he sticks his foot in his mouth and botches the proposal. Being insulted by the defeatist proposal, Anne leaves town on an assignment. After she's gone, he finds out that his recently-deceased grandfather's will stipulates that he gets nothing of a multi-million dollar fortune unless he's married by 6:05pm on his 30th birthday: tomorrow! Not being able to find Anne, Jimmie begins backtracking through his past girlfriends to find a wife.
The Bachelor (1999 )
Movie
Following the tragic death of her teenage son, Manuela travels from Madrid to Barcelona in an attempt to contact the long-estranged father the boy never knew. She reunites with an old friend, an outspoken transgender sex worker, and befriends a troubled actress and a pregnant, HIV-positive nun.
All About My Mother (1999 )
Movie
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.
The Big Kahuna (1999 )
Movie
Two air traffic controllers who thrive on living dangerously compete to outdo each other on several levels.
Pushing Tin (1999 )
Movie
An abused wife heads to California to become a movie star while her nephew back in Alabama has to deal with a racially-motivated murder involving a corrupt sheriff.
Crazy in Alabama (1999 )
Movie
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.
Drive Me Crazy (1999 )
Movie
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.
Hum Dil De Chuke Sanam (1999 )
Movie
Ben and Katie Jordan are a married couple who go through hard times in fifteen years of marriage.
The Story of Us (1999 )
Movie
In the panicky, uncertain hours before his wedding, a groom with prenuptial jitters and his two best friends reminisce about growing up together in the middle-class African-American neighborhood of Inglewood, California. Flashing back to the twenty-something trio's childhood exploits, the memories capture the mood and nostalgia of the '80s era.
The Wood (1999 )
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 )
