2. Chris Rock
His cutting commentary finds the funny in even the most taboo topics, which is why Chris Rock, an Emmy-winning comedian, devoted husband and loving father, never runs out of material. Chris has appeared on The Oprah Show 26 times, and over the years, he's teased Oprah about her hair—"Oh, that lucky Stedman!"—promoted box-office hits and revealed what it's really like to host the Academy Awards®.