15 (tie). Will Smith
Sometimes he's serious and other times he's hilarious...but he's always charming. Will Smith, one of the most powerful men in show business, has made 15 Oprah Show appearances since 1997. This celebrated actor, rapper, loving husband and father of three übertalented children isn't just a sit-and-talk type of guest—he likes to get involved. In 2005, Will even helped a few single guys score dates.