I'm like Che Guevara with bling on, I'm complex
Jay is like Che Guevara in that they are both revolutionaries, in a way. Jay started a “revolution” in the rap world/pop culture, and Che, a noted revolutionary, was essential to the movement that overthrew Fulgencio Batista, a U.S. backed dictator in Cuba. Needless to say, Jay doesn’t share Che’s economic opinions; he’s clearly showing off his wealth by wearing “bling” (jewelry).
The contradiction in the symbols shows the contradictions in Jay-Z’s character, which make him complex. Perhaps Jay is suggesting something about the duality of man.
Jay would famously wear a shirt with Che on it during the making of his MTV Unplugged special, and had previously referred to himself on record as “Jay Guevara”:
Criticism from a journalist about the chain/Che outfit was the impetus for this second verse
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