Jesse Williams

as Self - Narrator (voice)

David Axelrod

as Self - Senior Advisor to President Obama

Douglas Brinkley

as Self - Presidential Historian

Jon Favreau

as Self - Speechwriter for President Obama

Doris Kearns Goodwin

as Self - Historian

Valerie Jarrett

as Self - Senior Advisor to President Obama

Clark Judge

as Self - Speechwriter for Ronald Reagan

Cody Keenan

as Self - Former White House Director of Speechwriting