In a Manhattan cafe, word processor Paul Hackett (Griffin Dunne) meets and talks literature with Marcy (Rosanna Arquette). Later that night, Paul takes a cab to Marcy's downtown apartment. His $20 bill flying out the window during the ride portends the unexpected night he has. He cannot pay for the ride and finds himself in a series of awkward, surreal and life-threatening situations with a colorful cast of characters. He spends the rest of the night trying to return uptown.