15 Most Frequent Celebrity Guests

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.