Recurring Guest Characters David Daley 1 guest appearances Bassem Youssef 1 guest appearances Erin Gloria Ryan 1 guest appearances Rob Reiner 1 guest appearances Bruce Bartlett 1 guest appearances Maura Healey 1 guest appearances Bill Nye 1 guest appearances Matt Taibbi 1 guest appearances Jon Lovett 1 guest appearances Jen Psaki 1 guest appearances Jose Calderon 1 guest appearances Jeff Ross 1 guest appearances Sarah Lacy 1 guest appearances Molly Ball 1 guest appearances Rob Riggle 1 guest appearances Wesley Lowery 1 guest appearances Nikki Glaser 1 guest appearances Jamali Maddix 1 guest appearances Maya Wiley 1 guest appearances Richard Branson 1 guest appearances ⇤ « 1 2 3 4 » ⇥