Epic Rap Battles of History
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Most of the videos are crap, but the following ones almost killed Ciro Santilli of laughter:
Rasputin vs Stalin by Epic Rap Battles of History (2013)
Source. See also: cirosantilli.com/china-dictatorship/stalin.Monty Python has a few precursors to the "random famous people mixed together compting" format, although not in the rap fight format:
Communist Quiz by Monty Python (1970)
Source. Has a Wiki page: en.wikipedia.org/wiki/World_Forum/Communist_Quiz. Brings to mind: Video "Football, Football, Football by Mitchell and Webb".Philosophers' Football Match by Monty Python (1972)
Source. If you can understand the jokes, your philosophy level is pretty good. Like more than zero. Wiki page: en.wikipedia.org/wiki/The_Philosophers%27_Football_Match. Ciro loves how that page currently uses a standard footbal match template to describe the match!