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An expression describing someone who's an extreme liberal/leftist, often to the point of irritating the people around them. While Stalin is considered to be "left-wing," his politics are nothing like most modern liberals or leftists (since he was a neurotic totalitarian autocrat), so the expression is somewhat nonsensical and certainly a total exaggeration. It really rolls of the tongue, though, which makes it fun to use.
Guy #1: "Blah, blah, Noam Chomsky, capitalism is evil, EATING ANIMALS IS LIKE SLAVERY/THE HOLOCAUST/(insert irrelevant historical tragedy here), I hate America. brb putting on my Che Guevara t-shirt."
Guy #2: "Guy #1 needs to stop posting his whiny left-wing shit on Facebook. Goddamnit I voted for Obama and agree with the Democrats, but he's to the left of Stalin!"
Guy #3: "You know, Noam Chomsky and Stalin would hate each other."
Guy #2: "No shit, Sherlock. I'm just being melodramatic."
Guy #3: "Gotcha. Yeah, he needs to shut his ass up."
by Irritated Moderate August 24, 2013
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