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He grew up in Harvey, Illinois, and graduated from Ohio University in 1989. He is good friends with "Scrubs" creator and "Spin City" co-creator Bill Lawrence, with whom he has worked on most of his projects. Lawrence says his and Winston's friendship was the inspiration for the friendship of J.D. and Turk on "Scrubs" and Stuart and Carter on "Spin City". The character Randall Winston on "Spin City" was named after him, as was the character Randall, played by Martin Klebba, on "Scrubs". He is the inspiration for the character of Carter Heywood on "Spin City." He is openly gay and lives with his partner in Los Angeles. He is a member of the board of the Lupus Foundation of America.