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.
- Free
Movie
In 1978, a Kiss concert was an epoch-making event. For the three teen fans in Detroit Rock City getting tickets to the sold-out show becomes the focal point of their existence. They'll do anything for tickets -- compete in a strip club's amateur-night contest, take on religious protesters, even rob a convenience store!
Detroit Rock City (1999 )
- Free
Movie
Gabriel is a young, aspiring musical composer whose life seems stuck in the First Act. When his new musical number gets a critical reception, a theatre colleague, Perry, tells Gabriel that he needs to get a life before he can write about one – so he heads straight for his local gay bar.
Trick (1999 )
- Free
Movie
The band Fugazi is documented over a period of more than ten years (1987-1998) through performance footage and interviews with the band and their fans. Director Jem Cohen's relationship with band member Ian MacKaye extends back to the 1970s when the two met in high school in Washington, D.C.. The film takes its title from the Fugazi song of the same name, from their 1993 album, In on the Kill Taker. Editing of the film was done by both Cohen and the members of the band over the course of five years. It was shot from 1987 through 1998 on super 8, 16mm and video and is composed mainly of footage of concerts, interviews with the band members, practices, tours and time spent in the studio recording their 1995 album, Red Medicine. The film also includes portraits of fans as well as interviews with them at various Fugazi shows around the United States throughout the years.
Instrument (1999 )
- Free
Movie
In this 1999 documentary, Pete Townshend, Roger Daltrey and John Entwistle discuss the making of what many consider the Who's greatest testament to Townshend's songwriting talent: their classic album "Who's Next." Others close to the group weigh in with insights about the late Keith Moon's importance to the band. The retrospective also features unseen performances of tunes from the platter, including "Won't Get Fooled Again" and "Baba O'Riley."
Classic Albums: The Who - Who's Next (1999 )
- Free
Movie
A dark-themed and redesigned West End production of Rodgers & Hammerstein's seminal Broadway musical tells the story of farm girl Laurey and her courtship by two rival suitors, cowboy Curly and the sinister and frightening farmhand Jud.
Oklahoma! (1999 )
- Free
Movie
In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman.
Sweet and Lowdown (1999 )
- Free
Movie
Aja was the biggest selling album of Steely Dan's illustrious career. It was the first album by Donald Fagen and Walter Becker as a duo. Fagen and Becker recall the history of the album, along with Peg, Deacon Blues and Josie. Michael McDonald, later of the Doobie Brothers did guest backing vocals on Aja, the late British musician Ian Dury, record producer Gary Katz and the legendary session musicians who worked on Aja also contribute. This is a vivd portrait of a 70's record that is still as fresh and as memorable more than two decades after its release.
Classic Albums: Steely Dan - Aja (1999 )
- Free
Movie
In this fascinating Oscar-nominated documentary, American guitarist Ry Cooder brings together a group of legendary Cuban folk musicians (some in their 90s) to record a Grammy-winning CD in their native city of Havana. The result is a spectacular compilation of concert footage from the group's gigs in Amsterdam and New York City's famed Carnegie Hall, with director Wim Wenders capturing not only the music -- but also the musicians' life stories.
Buena Vista Social Club (1999 )
- Free
Movie
Rich Bower is an up-and-coming star in the hip-hop world. Everyone wants to be around him, including Raven and her fellow upper-class white high school friends. The growing appeal of black culture among white teens fascinates documentary filmmaker Sam Donager, who sets out to chronicle it with her husband, Terry. But before Bower was a rapper, he was a gangster, and his criminal past comes back to haunt him and all those around him.
Black and White (1999 )
- Free
Movie
Members of an opera company performing Donizetti's "Lucia di Lammermoor" find their lives parallel those of the characters.
Lucia (1999 )
- Free
Movie
When Martin Luxford (Hugo Speer) leaves jail, he decides to form a swing band, having been taught to play the saxophone by his cellmate Jack. Returning to his native Liverpool, Martin pulls together a backing band of misfits and loners, and recruits his ex-girlfriend Joan (Lisa Stansfield) as a singer. Things are complicated somewhat by the fact that Joan is now married to the policeman who arrested Martin, and when the band's first gig - at a heavy metal pub - goes badly, it seems as though the road to musical success may be a rocky one.
Swing (1999 )
- Free
Movie
Blind blues musician Paul Pena is perhaps best known for his song "Jet Airliner". In 1993, Pena heard Tuvan throat singing over his shortwave radio and subsequently taught himself how to reproduce these extraordinary sounds. This documentary follows him to Tuva, where he takes part in a throat singing competition. Languages featured in the film include English, Russian and Tuvan.
Genghis Blues (1999 )
- Free
Movie
A British documentarian profiles washed-up diva Jackie Washington as she prepares for her comeback concert.
Jackie's Back! (1999 )
- Free
Movie
Sangamam is a 1999 Tamil film directed by Suresh Krishna. The film stars Rahman, Vindhya, Manivannan and Vijayakumar in lead roles.
Sangamam (1999 )
- Free
Movie
The Trench tells the story of a group of young British soldiers on the eve of the Battle of the Somme in the summer of 1916, the worst defeat in British military history. Against this ill-fated backdrop, the movie depicts the soldiers' experience as a mixture of boredom, fear, panic, and restlessness, confined to a trench on the front lines.
The Trench (1999 )
- Free
Movie
The historical documentary Hitler Youth explores Adolf Hitler's maniacal construction of the titular organization - one comprised of young Aryan men who would rule the world by fear, intimidation and violence. Via a compendium of terrifying archival footage, the program documents the establishment of the Hitler Youth, its escalation from a membership of 13,000 to 10,000,000 within fifteen years, and the death of the organization following Hitler's suicide in 1945.
The Hitler Youth (1999 )
- Free
Movie
In 1943, while the Allies are bombing Berlin and the Gestapo is purging the capital of Jews, a dangerous love affair blossoms between two women – one a Jewish member of the underground, the other an exemplar of Nazi motherhood.
Aimée & Jaguar (1999 )
- Free
Movie
Marijuana is the most controversial drug of the 20th Century. Smoked by generations to little discernible ill effect, it continues to be reviled by many governments on Earth. In this Genie Award-winning documentary veteran Canadian director Ron Mann and narrator Woody Harrelson mix humour and historical footage together to recount how the United States has demonized a relatively harmless drug.
Grass (1999 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )
- Free
Movie
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 )