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22. President Obama Covers EBONY’s “25 Coolest Brothers Of All Time” 

Talk about swag on one thousand trillion. We all knew that Barack was a smooth cat, but this cover of EBONY Magazine certified it. In an issue dedicated to “Black Cool,” there was the leader of the free world. With some fresh Ray-Ban’s on, stepping out of the motorcade like he’s about to be followed by Ronnie, Bobby, Ricky and Mike. Not to mention he shared covers with fellow immaculately cool folks like Jay-Z, Prince, Denzel Washington and Marvin Gaye.

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