Onstage, he maintains the sort of effortless appeal of early Dave Chappelle, for whom Winfield frequently opens. He's performed standup on shows like Comics Without Borders, The Late Show with David Letterman, Last Comic Standing, and Comedy Central's Live At Gotham and he had a recurring role on the 2011 season of NBC's The Office. Thriving television career aside, Winfield's true skill comes across in live performances where his unique style shines.