He went on to study film and video at Columbia College in Chicago. There he made the award-winning 30-minute short "Paula," which established him as a filmmaker with an original vision that challenged convention. The film followed the story of a 17-year-old single black mother who works in a diner yet inspires the people around her more than any big-time hero. "Paula" was awarded the Midwestern Student Academy Award and went on to win prizes at seven student film festivals, including the Black Filmmakers Hall of Fame Award.

Bolstered by the success of "Paula," Tillman wrote and directed the feature Scenes For the Soul, which combines three different dramatic stories from urban Milwaukee. He and longtime producer Robert Teitel raised $150,000 through a group of Chicago investors -- ranging from doctors and lawyers to blue-collar workers enthused about the local project -- to finance the film. When the film was completed, Tillman had exactly $400 left in his pocket, but he drove with Teitel to Los Angeles and sold the film to Savoy Pictures for a cool million dollars. On the heels of Scenes For the Soul, Tillman began writing SOUL FOOD.