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
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 )
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 )
Movie
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 )
Movie
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 )
Movie
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 )
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 )
Movie
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 )
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 )
