He has been an associate producer on such shows as Champs, Day By Day, Brooklyn Bridge and Spin City. He produced Scrubs, and was co-nominated with Bill Lawrence in 2004 for Danny Thomas Producer of the Year by the Producers Guild of America. He has twice been Emmy nominated. He produced the pilots Nobody's Watching and Confessions of a Dog. He has also directed two episodes of Scrubs, My Self-Examination and My Buddy's Booty, and has appeared in episodes of the show as Leonard the security guard and Death. He is currently a producer on Lawrence's new show Cougar Town. For the ninth season of Scrubs he acts as co-executive producer.
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.
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