Recurring Guest Characters Steven Johnson 2 guest appearances Rev. Al Sharpton 2 guest appearances Michael Douglas 2 guest appearances H. W. Brands 2 guest appearances John Legend 2 guest appearances Henry Louis Gates Jr. 2 guest appearances Richard "Mack" Machovic 1 guest appearances Annette Gordon-Reed 1 guest appearances Jimmy Wales 1 guest appearances Robert Warrior 1 guest appearances John Lasseter 1 guest appearances Bill Maher 1 guest appearances Michael Strahan 1 guest appearances General Colin L. Powell 1 guest appearances Bruce Jenner 1 guest appearances Jeannette Walls 1 guest appearances David B 1 guest appearances Woody Norris 1 guest appearances Tom Brokaw 1 guest appearances Newt Gingrich 1 guest appearances