Comes from Starfox 64. A character would command fox to do a barrel roll in order to prevent being shot to deadness.
A barrel roll is when a fighter pilot makes his ship turn over, very quickly, in mid-air. It makes the wings harder to hit.
It's more common practice to shout this phrase at friends while they play video games. Especially if they can't do anything roll-like. The purpose is to be obnoxious, and quote old video games. Two of most peoples' favorite things.
"Son of a white boy, my Sim will not stop crying!"
"Quick, do a barrel roll!"
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