Eazy-E was invited to the White House by mistake in March of 1991. It was for a lunch fundraiser being held by then-president George H.W. Bush; Eazy accepted and paid $4,000 to attend. This was only a few years after the FBI had set its sights on the members of N.W.A for their album Straight Outta Compton, most notably for the song “Fuck tha Police.” Bush, a law-and-order Republican, was holding the dinner for a group called the Republican Senatorial Inner Circle. Eazy-E arrived in a suit jacket, with his signature L.A. Kings hat on his head, curled hair spilling from its edges.

I saw it at the time on a news clip, which I watched as a child who only knew that Eazy-E was a part of a rap group that scared people. But there he was, in the White House, with businessmen, senators, and a president who would likely prefer for his music to be banned. It was, at the time, rare access to be granted to any rapper, especially one who was seen as too intense for even some of rap’s younger, more eager fans. Not everyone was impressed. Ice Cube opened the final verse of the dis track he released a few months later, “No Vaseline,” by repeating the same line, a thinly veiled shot at his former bandmate: “I’d never have dinner with the president / I’d never have dinner with the president / I’d never have dinner with the president.”

I thought of that moment again when I saw the photo that surfaced just a few days before Barack Obama stepped out of the White House for the final time and left us to our wreckage. At first glance, it’s hard to make him out among the mass of familiar faces surrounding him: Busta Rhymes, Chance the Rapper, J. Cole, Alicia Keys, Common, Wale, DJ Khaled, Pusha T, Rick Ross, Janelle Monáe, and a few others. What struck me as the best part of the photo were the looks sported by everyone other than Obama himself. A couple of the rappers chose suits, sure. But some, like Ludacris, were dressed down in sweatshirts and sneakers. Even the ones who came out in nicer clothing had their own signature touches: Rick Ross letting his dress pants spill into a pair of black Adidas, Chance in his baseball hat. The conversation happening in the photo was one of comfort. These artists came as they were — not in defiance or spectacle, as Eazy-E did in 1991, to sit and smile in the faces of those who wished him to be anywhere but smiling in their faces. There is certainly a power in that, but the door that Barack Obama pushed open for rappers to be seen and comfortable in his White House presented a new type of power dynamic.

The optics of equality don’t do the same work as actual measures of equality, but they do mean something, particularly to people who have been denied access or visibility, or people who have been made to feel like the work they created was not worthy of equal consideration in the eyes of the country it was created in. There’s a lot to be said for the quality of black art made under the Obama administration, particularly during the second half of his time in office, after the shine of the first four years had worn off. And though I’m not sure how much of that it’s right to tie to Obama himself, he did make a fascinating companion to the times. What black people always understood about Obama that often got lost in non-black analysis of him was the immense difficulty in being the most visible man in the world and being unafraid to nod to blackness, even clumsily. I am not speaking about political moments here, but about aesthetics presented to people craving glimpses of a black president who, at his most comfortable, was unafraid to briefly talk like our friends or family might talk around a card table. A black first lady who, in public, had no problem cutting a look at someone that would both cause us to laugh and send a chill down our spines — a look that we understood, one passed down from some universal black ancestor we all recognize.

Even so, Barack Obama has never been nearly as cool as we’ve imagined or wanted him to be. Some of that, of course, is due to the constraints of the office. Some is due to the fact that he’s a generation or two ahead of us. But Obama’s connection to rap music and rap artists always felt logical, never false. Not necessarily because of his race, but because he always seemed to carry himself with the charisma and understanding of the stage that an MC has. His cadence, tone, and crowd control always felt rooted in rap music, which is rooted in a black oral tradition — people telling stories around porches, and then to instruments, and then to beats. It’s why his biggest moments onstage often carried gestures or language with a similar swagger. You could feel it in ’08, when he brushed dirt off his shoulders while a crowd erupted around him. Or when, during the first presidential visit to Jamaica in 32 years, he smiled while waiting for the audience to settle before shouting “Wha gwan, Jamaica!” into the microphone, causing the audience to burst into laughter. Or when he dropped the mic on the floor of the White House during his final correspondents’ dinner, two fingers pressed to his lips. It was always there, the promise of the Obama Moment that we could watch and see ourselves in.

For all the talk about how art can open the human spirit up to empathy, years of black people rapping about what’s happening in their communities hasn’t exactly softened much of America’s response to those communities or the people in them. This is most disappointing because rap was born out of and directly into a political moment, and the genre, through its decades of growth, hasn’t turned away from the core idea of archiving life as a political action. Rap has been a genre of speaking directly to politicians, though rarely to their faces. N.W.A weren’t the first rappers to be feared, but they surely incited a widespread panic among government officials who felt threatened by their message. To provoke someone in power enough that they call for your music to be banned was rap’s greatest trick, especially in the late ’80s and early to mid-’90s, when the government was easiest to provoke into such responses. It didn’t take rappers long to realize that their particular brand of storytelling wasn’t the type that could gain sympathy or understanding from white people in power, so why not play into the inevitable fear? When people in power who enforce and back violent policies pretend that the “rawness” of rap makes its creators less human, there is no use in imaging much of a bridge. The question isn’t about the obscene, but more about which obscenities people are comfortable crawling into bed with.

Obama, as much as we sometimes imagined him otherwise, is a politician. He was an American president, which means that he was tied into all of America’s machinery, which means that he was operating with a proximity to some level of violence at all times. But he was more than that, too, a complex and full-storied person. The problem with the way visible and complicated people of color and their histories are approached by the world around them is that they are, all too often, not afforded the mosaic of a full and nuanced history. If, in a song, a rapper has lyrics about enduring or even delivering violence, one might not think them worthy of having any concerns about violence in their communities. It’s one of the many fatal flaws of politics: not trusting those who are living or familiar with an experience to know what might be best for that experience.

To see Barack Obama throw open the doors to Jay Z and Beyoncé was encouraging but expected. I was much more encouraged to see him continually open the door or give nods to Kendrick Lamar and Pusha T — rappers whose lyrics still cause panic among some of the suits in Washington. Obama did this while knowing that it would open him up to the worst and most predictable kind of criticism: stale readings of rap lyrics by conservative pundits looking to discredit both the president’s commitment to politics and his commitment to their imagined American culture. Conservative pundits who, perhaps, once purchased drugs from drug dealers, now decrying drug dealers on television. Obama being a politician meant that a part of this was also performance, of course. But he didn’t ever appear to merely entertain rappers. He listened to them: Macklemore on addiction, Kendrick and J. Cole on black youth and criminal justice. The seat he offered them at the table was more than just an idle one. It was one that put artists in a room where they could be heard.

It may never be like this again. When I am asked what I will miss most about Barack Obama, I’m sure I’ll manage to think up something greater than the fact that he let rappers into the White House. I’m sure I’ll miss watching him in front of a crowd when he was on, and he knew he was on. The way he’d lean slightly away from the microphone and let a smile creep in while being bathed in some spectacular, hard-earned applause. I’ll miss the way he looked at Michelle — or, rather, the way they looked at each other, like no one else was watching. I’ll miss the shots of him playing basketball in sweatpants and a tucked-in shirt, a reminder that he was, indeed, never as cool as I wanted him to be. But I’ll always remember the door he held open for rap and all of its aesthetics — especially in the coming months, as funding for the arts is drained, and as the environment speeds toward unchecked disaster, and as we take to the streets again, weary but willing to fight all these things and more. I’ll remember it as rap shifts back into its contentious relationship with politics, and as the idea of having dinner with the president becomes, once again, something for which you’d receive shame and ridicule. I’m afraid and I don’t know what’s coming next, but I’m almost certain it will not be good. But above my desk now, there's a picture of Barack Obama, surrounded by rappers. Rappers on every side of him, dressed however they chose to dress. Rappers with their honest songs about the people who live and die in places that are often used as political talking points. Rappers standing proud with their proud president. All of those smiling black people in the Oval Office, miles away from a past where none of them, I imagine, ever thought they’d get to make it this far.