Special Guest Stars Elaine Stritch as Colleen Donaghy Guest Stars Will Forte as Paul L'Astnamé Rachel Maddow as Herself Alok Tewari as Dr. Singh Clarke Thorell as Russ Co Starring Marcella Roy as Young Liz Dante E. Clark as George Foreman Eli Bolin as Woggel #3 Adam Armstrong as Woggel #4 Mark Douglas as Ian Uncredited Jake Boyd as Young Jack Lars Engstrom as Kouchy