Baylor began as a sculptor but turned to painting as his preferred medium. While operating a trucking company, he honed his skills in an art program hosted by Milwaukee’s Pfister Hotel (2009) and eventually became a full-time artist. His stylized, figurative works share with Pop Art an interest in consumer culture—not just products but marketing. Baylor expanded his conceptual focus on art as commodity into actual commercial designs. Entrepreneur as much as artist, he opened the short-lived Reginald Baylor Studio as a generator for and purveyor of a variety of projects.