President Obama set a life goal for racial humor at the top of his customarily killer performance at the White House Correspondents’ Association Dinner. “I do apologize — I know I was a little late tonight,” Obama said to the 2,700 guests at the Washington Hilton. “I was running on C.P.T., which stands for ‘jokes that white people should not make.’” This was a backhanded slap at Bill de Blasio, the white mayor of New York City who has an African American wife and biracial children and caused a stir last month using the phrase during a political comedy sketch. 

Now, if there are things white people should not say, then there are definitely things black people should not say. Let me be more specific. African Americans know there are things that should never be said outside the safe cultural confines of the barbershop, beauty shop, backyard barbecue or momma’s house. Nothing exemplifies this better than two of the last words of Larry Wilmore’s disaster of a nerd prom performance.  

But behind that joke is a humble appreciation for the historical implications for what your presidency means.
When I was a kid, I lived in a country where people couldn’t accept a black quarterback. Now think about that. A black man was thought by his mere color not good enough to lead a football team — and now, to live in your time, Mr. President, when a black man can lead the entire free world.
Words alone do me no justice. So, Mr. President, if i’m going to keep it 100: Yo, Barry, you did it, my nigger. You did it.

If you read the Urban Dictionary definition of “my nigger,” you’ll see that Wilmore was forging a personal bond with Obama. Judging by the double tap of his chest and hug of Wilmore in response, the president appreciated the gesture. But use of the n-word by African Americans is a complex thing.

Yes, many use it as a term of endearment for close friends and family, as Wilmore did. As a child and even today I wonder how so much love could be derived from such a hateful word.

Many say it to reclaim the ugliest word in the English language used to devalue their enslaved ancestors and subsequent generations. The NAACP may have held a public burial of the n-word nearly a decade ago. But it is exhumed daily by young people of all races who mindlessly hurl the insult seemingly without a care for its painful history.

And many African Americans use it to make a constructive point, as when Obama dropped the N-bomb during a podcast interview with Marc Maron last year. “Racism. We are not cured of it,” the president said. “And it’s not just a matter of it not being polite to say ‘nigger’ in public. That’s not the measure of whether racism still exists or not.”

But never before has the n-word been used to address the president. At least, not in public and most definitely not to his face. That’s why Wilmore’s use of it was as shocking as it was disrespectful. And that’s why many African Americans in the room and watching on television were appalled by Wilmore’s excessive and inappropriate down-home familiarity with the leader of the free world in front of the world.

Even before he walked into the Oval Office in January 2009, Obama’s detractors had questioned his authority and done everything possible to erode the legitimacy of his presidency. From unprecedented snubs of the chief executive to heckling him at a joint session of Congress in his first year, the president’s critics have done everything but call him the n-word. But they don’t have to now that Wilmore has done it for them.

Sure, there were and are blacks who loved what Wilmore said. They think that by “keeping it 100,” a latter-day “keeping it real,” Wilmore expressed the undeniable pride African Americans have for Obama, the first lady and everything the first family means and represents to them. But the White House Correspondents Association dinner was neither Wilmore’s barbershop nor his momma’s house. Obama is president of the United States and should have been accorded the respect that comes with the office — especially by someone who considers himself family.

Follow Jonathan on Twitter: @Capehartj