The White Boy Shuffle is a novel posing as a memoir of a reluctant new hero, Gunnar Kaufman. The novel begins with Gunnar's earliest memories of being a black juvenile beach bum in Santa Monica and chronicles the hilarious exploits that lead him to become a young adult regarded as the black messiah.

Gunnar begins his own history by telling the history of his male ancestors. Some of his ancestors are involved in significant moments of history, such as Euripides Kaufman who is the youngest slave in history to purchase his own freedom and who is instrumental in helping to provoke the American Revolutionary War. Other relatives such as Swen Kaufman have the dubious distinction of being the only known black man to run to the American south and into slavery. More recent relatives include the likes of Wolfgang Kaufman who first paints Segregation signs in Tennessee and then, while working as a janitor in Chicago, helps to create the radio program Amos n Andy. Gunnar's own father, Rolf Kaufman, works as a sketch artist for the Los Angeles Police Department.

Gunnar describes a happy childhood in Santa Monica. He remembers being the "funny, cool black guy," and his days away from school are filled with bodysurfing and reading on the deck of his mother's two-story townhouse. At school he finds the obsession with multicultural issues ridiculous since almost all the students are white, and the teachers seem to believe that the best way to handle racial distinctions is to pretend not to notice them.

After Gunnar's mother becomes alarmed that her children have completely lost touch with their black heritage, she moves them from their affluent Santa Monica home to what Gunnar describes as a West Los Angeles ghetto called Hillside. From the moment Gunnar arrives he is a target. He dresses and speaks differently from the other residents, and the more he tries to fit in the more he puts himself in danger. Three events occur almost simultaneously that change Gunnar's standing in Hillside. He discovers that he has an amazing natural talent for the game of basketball, he finds his poetic voice, and he becomes friends with the most feared young gangster in Hillside.

Though on the surface Gunnar appears to have assimilated into the Hillside culture, he retains his genius intellect. As his fame from basketball increases, so does his renown as a street poet. Unfortunate external events cause Gunnar to get involved in some illegal activity, and in exchange for his father the policeman not turning Gunnar over to the authorities, Gunnar attends his final two years of high school at a wealthy suburban school.

As soon as Gunnar finishes high school his friends and family have a surprise for him. They have ordered him a mail-order bride, and Gunnar gets married before leaving to attend Boston University. Gunnar finds that his fame has preceded him to Boston University, and before he even has the opportunity to complete any classes he is hailed as the greatest of street poets and the new voice of the black American. Gunnar's fame grows exponentially, and his life spins out of control in an ever-increasingly hilarious way.