• 
  Jamie Kaler

   Himself - Host (20 episodes, 2013-2014)
• 
  Francis French

  Self
• 
  Chance Gibson

  Frank Morris
• 
  Eláyne Paola Coba

  Doña Marina
• 
  Randy Burrell

  Blackbeard's Killer
• 
  Shaun Irving

  Cavalry Trooper
• 
  Brian McTamaney

  Clarence Anglin
• 
  Dan Grossman

  Self - Aviation Historian

• 
  Devin Albert

  Surprise Me Man
• 
  M.H.W. Brands

  Self - Phd., Prof. of History, Texas University at Austin
• 
  Joe Nickell

  Self - Investigator, Skeptical Inquirer Magazine
• 
  Christian Cipollini

  Self
• 
  Anne Collier

  Self - Historian
• 
  Von Lewis

  John Dillinger
• 
  Don Cardale

  Judge

• 
  Robert Fabiani

  King Ferdinand
• 
  John Paul Andrews

  Prison Guard
• 
  Jeffery Clarke

  Self - Historian
• 
  Saye Yabandeh

  Queen Isabella
• 
  William Leon

  Francis Billington