Jonathon William Love is an odd young man. His father is a millionaire, yet he lives in a shabby two bedroom apartment in East Milwaukee with his chauvinist roommate, Aaron, and he works for minimum wage at a flower shop, the owner of which is a tittering, senile floraphile. He graduated valedictorian in his class, but he spends his time struggling to become the picturesque "starving artist".

When his father, Jerry, dies suddenly of the common cold, Johnny inherits half of the fortune and estate, and is expected to carry on in the company where his father left off. As his mother quickly deals with her grief, she pulls him into the cutthroat world of business and wealth.

Trying to escape his impending fate, Johnny bicycles to the countryside to paint and get perspective. While painting, sitting on a train track, and listening to his MP3 player, he narrowly misses getting squashed by a high speed freight train. A hobo girl, Jessy Wilder, jumps off to see if he's dead. She picks up his painting and finds his perspective to be absolutely, "all wrong." Inviting herself into his life, she decides to teach Johnny Love a thing or two about what it means to be free.