His first film shot with sound, Feelings is a two and a half minute movie made as an NYU film school assignment in 1984. Solondz himself takes the lead role of a sensitive young man who finds he can no longer endure life without his beloved. Photographed by Andy Day, the film is set to Todd Solondz's personal rendition of the song "Feelings" by Morris Albert.

Solondz’s 1985 student short film “Schatt’s Last Shot” provides an ideal entry point to his unflinching universe of dark comic despair. A young Solondz stars in the 10-minute short as geeky high schooler Ezra Schatt, a neurotic, primitive headcase of the young Woody Allen variety. Buried under thick, unseemly glasses and an endlessly dazed expression, Ezra’s worst enemy is basketball. Unable to make a single basket under the brutal pressures of his vulgar gym teacher (“You’re shit, Schatt!”), Ezra also fails at both impressing the cheerleader of his dreams and realizing his aspirations of attending MIT.

Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and her son depart for New York City to make a fresh start. Unfortunately, Tony has set his sights upon Angela -- and so has an undercover FBI agent looking to use her to bust Tony.

An unsuccessful playwright faces trials and tribulations as he seeks to find himself in New York City.

A misanthropic author, a single mother and waitress, and a gay artist form an unlikely friendship after the artist is assaulted in a robbery.

A foreign musician is stranded at a New York City area hotel after the airline he was ready to take home collapses and replacement carrier flights are delayed. He bonds with a singing chambermaid.

The lives of several individuals intertwine as they go about their lives in their own unique ways, engaging in acts which society as a whole might find disturbing in a desperate search for human connection.