With his critically acclaimed third album, Dark Sky Paradise,...

With his critically acclaimed third album, Dark Sky Paradise, and his recent collaborative EP with L.A. songstress Jhené Aiko under the name Twenty88, Big Sean has made his name on witty wordplay and a gold chain–sporting shirtless swagger that’s a direct descendant of Tupac Shakur’s. “Sometime I would look back on pictures after a show, I’d be like, ‘Man, my outfit looked better than me with my shirt off,’” he says.

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Photo: Thomas Falcone

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