Born in Toledo, Ohio, Kennedy grew up in Ridgewood, New Jersey, working in a picture frame store while he was in high school. After studying sculpting and conceptual art at New York's School of Visual Arts, Kennedy graduated with a sociology degree from the University of Wisconsin–Madison. At the University he was an active member of the Pail & Shovel Party, a student group dedicated to bringing humor to student government via absurdist and playful pranks. Kennedy drew posters and flyers for the group and took part in many activities, including the famous Pink Flamingo planting. From 1983 to 1988, he served as cartoon editor of Esquire where he edited and co-wrote Lynda Barry's Modern Romance. At the same time, Kennedy was a humor book agent as well as a cartoon consultant and editor for m