In this episode the hosts discuss the lives and legacies of Henry VIII and Oliver Cromwell. These two dictators battle it out in Round 6 of the knock-out tournament to determine the single greatest dictator of all time. The hosts discuss Henry's determination to produce an heir, his creation of the Church of England, his cruel and numerous methods of execution and his lasting legacy. They also discuss Cromwell's rise to power, his brutal decimation of the Irish, his execution of the King, the Puritan bans on most forms of fun and the impact of his short rule. One of these two dictators will be eliminated from the tournament and the other will remain in contention to be crowned history's greatest dictator.