I chuckled in amusement in the Spring of 2012 as President Obama regaled the audience with his humor in what has to be one of the most enjoyable roles for the commander-in-chief: standup comedian at the annual dinner for the White House Correspondents’ Association. Obama’s pace and timing were a lot better than those of the professional comics charged with bringing down the house that night. Jimmy Kimmel rushed through his jokes a bit too nervously and even stepped on some of his lines. Obama, on the other hand, was smooth and effortless, confident that his zingers would find their mark. His swag quotient was also pretty high that night. He let it be known that his musical prowess consisted of more than a melodically accurate one-off rendition of a line from Al Green’s R&B classic “Let’s Stay Together,” which he had delivered at an Apollo Theater fundraiser three months earlier. Obama’s version of the soul legend’s tune went viral in Black communities as a sign of the president’s effortless embrace of Black Culture despite the criticism that he keeps Blackness at bay. At the Apollo fundraiser, after drawing huge applause from his largely Black audience, Obama addressed the Rev. Al Green, who, along with India Arie, had sung at the affair, by saying: “Don’t worry Rev., I cannot sing like you, but I just wanted to show my appreciation.” At the Correspondents’ dinner, Obama showed his appreciation for Hip Hop and proved his Rap bona fides, and not just by citing the easy or apparent fare. To truly strut his stuff, he’d have to display an aficionado’s grasp of Rap Culture’s range and appeal and flash a little insider savvy.
The set-up for Obama’s Hip Hop coolness was a perfect storm of conspiracy theory and Black cultural signification. “Now, if I do win a second term as president,” Obama teased his audience, “let me just say something to all my conspiracy oriented friends on the right who think I’m planning to unleash some secret agenda.” He paused for a few seconds, then hit