Ye always had something to prove
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The ‘Dropout Bear’ cover
To contextualize the cover of West’s first album, compare it to the debut album of one of hip-hop’s biggest stars at the time, 50 Cent, whose “Get Rich or Die Tryin’” cover is an image of the shirtless rapper wearing Gucci pants and a diamond cross in front of shattered glass with a giant bullet hole at its center. West dressed as a college mascot bear sitting alone on gym bleachers must have seemed silly, strange and decidedly uncool — which is exactly why it’s so memorable. Only adding to its boldness is the fact that there are no words on the cover — aside from a parental advisory warning — as if West believed that everybody should already know who he was.