Recurring Guest Characters Jamelle Bouie 1 guest appearances Brad Smith 1 guest appearances Antoni Porowski 1 guest appearances Sonia Sotomayor 1 guest appearances Bashir Salahuddin 1 guest appearances Diallo Riddle 1 guest appearances Megan Twohey 1 guest appearances Edward Snowden 1 guest appearances Nick Cannon 1 guest appearances Jameela Jamil 1 guest appearances Mark Sanford 1 guest appearances Anand Giridharadas 1 guest appearances Jacqueline Woodson 1 guest appearances Tyler Blevins 1 guest appearances Chanel Miller 1 guest appearances Rand Paul 1 guest appearances Will Smith 1 guest appearances Taika Waititi 1 guest appearances Cyntoia Brown 1 guest appearances Ali Wong 1 guest appearances ⇤ « 23 24 25 26 27 28 29 30 31 32 » ⇥