• 
  Louis Armstrong

  Himself (archive footage)
• 
  Eli Steele

  Himself - Father to Jack & June
• 
  Justin Gordon

  (voice)
• 
  Hillary Clinton

  Herself (archive footage)
• 
  Jesse Jackson

  Himself (archive footage)
• 
  Tim Groseclose

  Himself - UCLA Political Science & Economics Professor
• 
  Marcia Dawkins

  Herself - Professor & Author
• 
  Eric Jackolski

  Himself

• 
  Angie McKee

  Herself
• 
  Richard Sander

  Himself - Professor of Law: UCLA Law School
• 
  Katelin Wagner

  Herself - College Applicant
• 
  Rita Steele

  Herself - Grandmother to Jack & June
• 
  Clay Cane

  Himself - Journalist Jersey City
• 
  Jennifer Ceci

  Herself - UCLA, B.A., Harvard Ed.M: Film Production Management
• 
  Rachel Dolezal

  Herself (archive footage)

• 
  Donald Trump

  Self
• 
  Scott Brown

  Self - Senator Massachusetts
• 
  Elizabeth Warren

  Self