Gay Films from 1999

Discover gay movies and short films released in 1999, featuring gay films from around the world across drama, romance, comedy, thriller and more. You can also find out where to watch these films.
The Talented Mr. Ripley

The Talented Mr. Ripley

1999 Drama, Thriller
In the late 1950s New York, underachiever Tom Ripley is sent to Italy to retrieve the spoiled millionaire playboy Dickie Greenleaf. When the mission fails, Ripley resorts to extreme measures.
Rites of Passage

Rites of Passage

1999 Drama, Mystery, Thriller
An attorney and his father attempt to resolve familial tensions during a trip to their isolated family cabin, interrupted by two escaped convicts.
Hit and Runway

Hit and Runway

1999 Comedy, Drama, Romance
Alex and Elliot, an unlikely duo, collaborate on a film featuring a New York cop undercover as a fashion model.
Burlesk King

Burlesk King

1999 Drama
Harry, son of an abusive American father and Filipina mother, escapes to Manila seeking vengeance. Working as a macho dancer, he forms a supportive circle of friends and confronts his past.
Trick

Trick

1999 Comedy, Musical, Romance
Two young men navigate Manhattan's gay scene in search of privacy.
Story of a Bad Boy

Story of a Bad Boy

1999 Comedy, Drama, Musical, Romance
Seventeen-year-old Pauly is a closeted high school kid with big dreams. His dad wants him to make the track team, his mom wants him to excel in the band, and Pauly just wants to get closer to the new student teacher.
Speedway Junky

Speedway Junky

1999 Drama, Romance
Johnny's aspirations of becoming a stock car racer lead him to a world of hustlers and unexpected connections in Vegas.
Flawless

Flawless

1999 Drama
A conservative guard's stroke leads to singing lessons with a drag queen, challenging his beliefs.
American Beauty

American Beauty

1999 Drama
A father faces a mid-life crisis when he becomes infatuated with his daughter's charismatic best friend, navigating desire, morality, and the complexities of aging.
Second Skin

Second Skin

1999 Drama, Romance
A doctor and a married man's extended affair affects the lives of not only the men involved, but the wife as well.
Back Room
SHORT FILM

Back Room

1999 Drama, Romance
A back room in Barcelona's gay club hosts a complex web of desires and emotions among patrons, revealed through introspective voice-overs.
The Einstein of Sex

The Einstein of Sex

1999 Drama
The life story of Dr. Magnus Hirschfeld, a German Jew and pioneer in sexology, focuses on his fight against anti-sodomy laws and establishment of the First Institute of Sexual Sciences in 1920s Berlin, amid rising Nazi threats.
Taboo

Taboo

1999 Drama, Thriller
A new samurai militia member becomes the object of desire, testing the unit's discipline.
Oi! Warning

Oi! Warning

1999 Drama
A German teen torn by identity drifts toward a skinhead gang while forming an unlikely bond with a gay leftist punk. The clash between their worlds escalates into violence, exposing the fraught tensions between subculture and sexuality.
Greater Than Half
SHORT FILM

Greater Than Half

1999 Drama
Raymond finds solace within himself while Simon loses himself in other people. Both find security within their own obscure lifestyles, avoiding their fears of the world. When faced, Raymond and Simon learn to open their eyes and see themselves in each other.
Boys Briefs

Boys Briefs

1999 Compilation
Compilation of six gay short films.
Looking for an Angel

Looking for an Angel

1999 Drama
Takachi, a young adult film star from a small town in Japan, is found dead. His death reveals his true emotions, and his two best friends travel back to his hometown, Kochi, where they discover his angelic side.
$30
SHORT FILM

$30

1999 Comedy
A father arranges for his closeted son to spend a night with a sex worker.
Angel in the Toilet
SHORT FILM

Angel in the Toilet

1999 Comedy
Entering a restroom, a young man finds himself pursued by another man interested in him, embarking on a fable about an angel residing in the restroom, offering love to lost souls.
Tommy Trips
SHORT FILM

Tommy Trips

1999 Drama
Glass keeps breaking every time Thomas gets too close to his favorite classmate, Quentin. If he comes out to him will more than glass be shattered?
I Can Just Imagine
SHORT FILM

I Can Just Imagine

1999 Drama
At 30, Paulo is still attached to his protective mother, silent father, domineering boyfriend, and his cabaret roles, losing himself in others' lives and the songs of Shirley Bassey.
Piglets
SHORT FILM

Piglets

1999 Comedy
Two young men's intimate moment is disrupted by an interfering neighbor's antics.
Boy Next Door
SHORT FILM

Boy Next Door

1999 Drama
Who's the hunky new neighbor across the street? Teenage Charlotte and her brother, Chris, both want to know. Cruel sibling rivalry abounds as each woos the new guy while trying to undercut the other's advances. Three is definitely company!