Recurring Guest Characters Ana Marie Cox 1 guest appearances Douglas Brinkley 1 guest appearances Deborah Lee James 1 guest appearances Eric Fanning 1 guest appearances Wesley Lowery 1 guest appearances George Packer 1 guest appearances Q-Tip 1 guest appearances Ryan Speedo Green 1 guest appearances Mahershalalhashbaz Ali 1 guest appearances Tomi Lahren 1 guest appearances Ray Mabus 1 guest appearances Evan McMullin 1 guest appearances DJ Khaled 1 guest appearances Tim Gunn 1 guest appearances Raegen McDonald-Mosely 1 guest appearances Michael Che 1 guest appearances Omar Saif Ghobash 1 guest appearances Luthor 1 guest appearances Susan Goldberg 1 guest appearances Aasif Mandvi 1 guest appearances ⇤ « 7 8 9 10 11 12 13 14 15 16 » ⇥