Guest Stars Wanda Sykes as Shirley Chisholm Kym Whitley as Florynce Kennedy Colton Dunn as Conrad Chisholm Nick Robinson as Robert Todd Lincoln Ike Barinholtz as General Ulysses S. Grant Marla Gibbs as Ruby Seale Zahn McClarnon as Private Mingoes Tyler James Williams as Private Mason Dixon Tim Baltz as Lieutenant Henry Honeybeard Jason Acuña as Russian Craig Cackowski as Joseph Stalin Wanda Sykes as Harriet Tubman Chris Pontius as Russian Assassin Preston Lacy as Russian Noble James Adomian as President Richard Nixon Christopher Thornton as President Franklin Roosevelt Nick Kroll as Galileo Tim Bagley as Doctor George Wallace as Governor George Wallace Andrew Rannells as Sergei Dan Bakkedahl as Winston Churchill Brandon Kyle Goodman as Clay Co Starring Katherine LaVeaux as TBD Jon Daly as Glenn Scott MacArthur as Fleetus Edgar Blackmon as Audience Member Eric Nenninger as TBD David Stassen as Sitcom Director