Che Guevara was a Marxist revolutionary, who got famous by wearing a beret. He is the only reason berets are still cool.
Born in "Argentina" (where ever that is), he was often dubbed as "The White Mr. T of his time"
Che being already being far to awesome to be seen in a place like Tierra del Fuego, he decided to go on a motorcycle trip to a leper colony, just to prove he was so bad-ass, he couldn't catch leprosy.
On the trip, he saw the poverty of South America. Che was appalled that children were dying from a lack of medical care due to poverty and decided some asses needed to be kicked in the name of ESTABLISHED COMMUNISM.
In 1953, Fidel Castro was an up and coming revolutionary, beginning a plot to overthrow Fulgencio Batista's overblown hat (and possibly the oppressive right wing government).
He could have won, with more functional headgear
Castro led a small band of revolutionaries against the Moncada Barracks on the 26th of July. The small group was crushed, presumably because the weren't shit-faced drunk following the 25th of July feast. Castro's force was outnumbered, and had no hope of competing with an enemy that wasn't massively hung-over.
Solo para Los Companeros de la Revolucion
In 1955 Che met Fidel and Raul Castro in Mexico city. Guevara had recently graduated from Med school, and after joining forces to overthrow Batista, the three then performed a magic ritual where they touch their class rings together and yell "Shablagoo!" Using their Marxist Powers the three transformed into Hannibal Barca (the dude with the elephants), Guy Fawkes and Otto Skorzney [Citation Needed]. They then began arming their close friends with surplus American weapons from WWII, and Camilo Cienfuegos had an FAL with a modded controller [Citation Needed].
Now all of the patrons of cracked.com with a PHD in history (all 2.6777 of you) will know what what happens:
Castro lands in the eastern province, El Oriente, with 80-ish Guerrillas and 50-ish Guns. Luckily "Pombo" brought a copy of the Necronomicon along for good luck [Citation Needed].
Sorry, Wikipedia was a stub [Citation Needed]
Che read the Necronomicon, and miraculously didn't go insane. This summoned Cthulhu to the Sierra Maestra mountain range, where Batista's army was DEVOURED [Citation Needed]. Castro, Che and the 26th of July movement then spent three years walking across the country, basking in their victory, and proclaimed that they won on 1-1-59.