Billy Crystal

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15. Billy Crystal
Funnyman Billy Crystal has been making Oprah and her viewers laugh since Season 2 of The Oprah Show. On his first of 15 appearances, Billy used his "shtick" to promote Comic Relief, a nonprofit organization that helps the homeless. Since then, this celebrated comedian has returned to Oprah's stage to joke about everything from hosting the Oscars® to life as a dotting grandfather.