Guest Stars Tim Baltz as Various Characters Michael Coleman as Various Characters Tymberlee Hill as Various Characters Mort Burke as Various Characters Maria Blasucci as Various Characters Jeremy Tutson as Various Characters Bennie Arthur as Various Characters Craig Cackowski as Various Characters Jen Kirkman as Herself (Narrator) Jenny Johnson as Herself (Narrator) Molly McAleer as Herself (Narrator) Courteney Cox as Edith Wilson Alia Shawkat as Frances Cleveland Paget Brewster as Emma Folsom Casey Wilson as Dolley Madison Bobby Moynihan as Grover Cleveland Ian Roberts as James Madison Uncredited Tiffany Simone English as Orphan Girl