The hosts unravel the lives and legacies of two Roman Emperors; Caligula and Nero. 

They discuss the Caligula's stellar ancestry, the origin of the nickname 'Caligula', his adoption by the Emperor Tiberius, his suspicious succession to Emperor, his cruel reign, sexual perversions and his eventual assassination. 

They also discuss Nero's many connections to Emperor Claudius, his unbelievable mother Agrippina the Younger, his tutor Seneca, his cruel and disinterested reign, his obsession with the arts, his handling of the Great Fire of Rome and the revolt that led to Nero's suicide.

These two dictators battle it out in Round 16 of the knock-out tournament to determine the single greatest dictator of all time. One of these two dictators will be eliminated from the tournament and the other will remain in contention to be crowned history's biggest dictator.