Henry's father kicks him out of the house. Henry Chinaski (Matt Dillon) considers himself a writer, and on occasion writes. Mostly he quests for the booze and women that sidetrack and seduce, rather than inspire greatness.

When he falls for Jan (Lili Taylor), the soulful connection fails to save either from their self-destructive ways, and the relationship totters between earnest connection and reflective loathing. With exceptional performances that capture the intoxicated journey though life and art, Factotum is the story of a man living on the edge; a writer who risks everything, tries anything, and finds poetry in life's pleasure and pain.