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.

Young Henry Hill (Ray Liotta), with his friends Jimmy (Robert De Niro) and Tommy (Joe Pesci), grows up in the mob and works very hard to advance himself through the ranks. He enjoys his life of money and luxury, but is oblivious to the horror that he causes. A drug addiction and a few mistakes ultimately unravel his climb to the top. Based on the book "Wiseguy" by Nicholas Pileggi.