After high school, Millionaire attended the Massachusetts College of Art, where he majored in painting. While in college, he began drawing houses for money; this, along with occasional illustration jobs, would be his primary source of income for the next 20 years. After graduating from college, he moved from place to place, living in Boston; Florida; California; and Italy; before settling in Berlin for five years during the 1980s. Returning to the U.S. in the early '90s, he moved to Brooklyn, where he began drawing a regular comic strip, "Medea's Weekend", for the Williamsburg newsweekly "Waterfront Week".