“I Have 99 Problems and Now Jay-Z Is One,” – President Obama

The annual White House Correspondent’s Dinner is typically a light-hearted affair, and this year’s installment was no exception. The Dinner tends to serve as an opportunity for the President to show off his sense of humor and pop culture savvy, and with a President as charismatic as Barack Obama, these events tend to be ripe with entertaining moments.  

While Obama obviously poked fun at himself and at those right wing media outlets who consistently have derided him throughout his two terms in office, he made sure to offer up enough hip-hop references to have the community talking for quite some time. Prior to the President stepping to the podium, the crowd in attendance was treated to DJ Khaled’s “All I Do Is Win.” Obama clearly enjoyed the moment, even synchronizing his hand gestures to match the chorus.


“How do you like my new entrance music?” Obama jokingly asked the audience, waiting for those assembled to sit back down before going right into the rest of the speech.

Later on, Obama had the chance to take a slick jab at Jay-Z, who caused a media frenzy with his visit to Cuba and subsequent “Open Letter.” Talking about issues that he has to deal with that are out of his control, Obama said, “It’s unbelievable… I have 99 problems and now Jay-Z is one of them.” Interestingly enough, the President does not appear to be as concerned about Beyonce, who also went on the trip with her
husband and created her own controversy at the recent inauguration by apparently lip-synching the National Anthem.

With the President entrenched in office for three more years at least, will the President continue to embrace hip-hop as openly as he did tonight, albeit in a joking manner? Is there any way Hov can offer up an appropriate response to Obama’s comments? More importantly, has the President discovered that Khaled’s ad-libs provide the self-confidence boost one needs to win a grueling election?