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1. Nirvana - Smiley Face

While their music was never quite as cheery as the smiley face on this famous shirt, the play between their sound and the graphic was perfect. Allegedly drawn by singer Kurt Cobain, the face has been rumored to be a reference to Axl Rose and even a play on the logo of a club Cobain would frequent. Recently, a Rihanna shirt riffed on the sketch, turning the smile into a frown.

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