Recurring Guest Characters Adam Grant 1 guest appearances Arthur C. Brooks 1 guest appearances Mitt Romney 1 guest appearances Dolly Parton 1 guest appearances Sean Penn 1 guest appearances Oprah Winfrey 1 guest appearances Peggy Whitson 1 guest appearances Luke Russert 1 guest appearances Mikaela Shiffrin 1 guest appearances Adrianne Haslet 1 guest appearances Jim Nantz 1 guest appearances Serena Williams 1 guest appearances Dan Buettner 1 guest appearances Bono 1 guest appearances Drew Barrymore 1 guest appearances Hillary Clinton 1 guest appearances Chelsea Clinton 1 guest appearances Jon Stewart 1 guest appearances Lonnie Bunch 1 guest appearances Katy Perry 1 guest appearances ⇤ « 1 2 » ⇥