In 2009, JAY-Z made an appearance on The Late Show with David Letterman to promote his underwhelming album, The Blueprint 3. Seemingly aware of Letterman’s penchant for dry humor and slyly cutting remarks, Jay decided to turn the tables on the host, deliberately misunderstanding his questions, and carefully crafting his responses to offer as little substance as possible.
After a particularly strained attempt to get Jay to open up about his life as a newlywed, Letterman abruptly abandoned his line of questioning. “Hey, let me ask you a question about the New Jersey Nets,” he said, apropos of nothing. Sensing that the host was floundering, Jay paused for just the right amount of time before sarcastically replying, “that’s a great segue.”
Say what you will about the music he was on the show to promote, but in that moment, JAY-Z was the coolest person on Earth.
The concept of “coolness” is something that carries very little weight outside the context of high school. Within adult life, there are no predetermined social stratifications for people to fit neatly into. Former star athletes, fans of Magic the Gathering, and everyone in between all stand on equal playing ground. There are no superficial sets of skills, hobbies or aesthetics that define whether or not a particular person is “cool.” Yet, every once in awhile, I’ll meet someone who reminds me why society isn’t quite ready to do away with the concept entirely—someone who appears to be at ease in all situations; someone who moves through the world as if it’s been greased with coconut oil; someone who is naturally, effortlessly cool.
When I was younger, it seemed like one of the prerequisites for being a successful rapper was to be one of these people. I’d watch interviews with JAY-Z and Biggie, and I’d notice that they carried themselves with a certain unassuming swagger. They were confident without being obnoxious, they were endlessly compelling, and they were wryly funny in a way where they seemed almost indifferent towards this skill.
Put another way, they didn’t strike me as the type of people who had ever been burdened by a surplus of neuroses. When they moved culture forward, it almost seemed like they were doing so in their spare time. They accidentally created new slang, they inadvertently sparked new fashion trends, and they inspired large digressions in the art as if doing so was as simple as solving the puzzles on a toddler’s television show—what do you mean, “can you see the mountain?” It’s literally the only landscape visible on the screen. Stop patronizing me, children’s entertainer.
Perhaps I’m romanticizing my hindsight or I’m blinded by nostalgia, but this isn’t a feeling I’m struck with when looking at the current crop of rappers. In comparison to the previous generation, today’s collection of rappers seems like a ragtag bunch, spontaneously thrown together to fumble their way through a heist in a bad action-comedy movie. The most popular rappers of this current generation don’t seem to possess an endless store of charisma like, say, Q-Tip or Snoop Dogg, they just seem like regular people; people who just happen to be good at rapping.
Much of this is a result of a necessary shift in the music that began to take place around the release of Kanye West’s 2008 album, 808s & Heartbreak. With the release of 808s, Kanye provided listeners with a reprieve from the endless bravado that had begun to suffocate the genre’s creativity. By no means was Kanye the first rapper to infuse vulnerability into his music, but there was something that felt so pioneering about his dramatic departure from Graduation. As it’s been said many times before, the success of 808s gave way to the rise of Drake, which subsequently led to the rise of hundreds of Drake clones, and the snowball effect followed. It turns out, listeners liked the idea of being able to relate to rappers in an emotional capacity that wasn’t just aspirational. It didn’t take long for us to grow accustomed to rap songs filled with lyrics custom-made for subtweeting our ex-spouses.
Yet, as rappers have taken to rapping increasingly about themselves, listeners have begun to subject them to the same standards we’d subject anyone to if they were to talk at length about their lives—we ask for them to be self-aware. Everyone knows and dislikes at least one person who is constantly verbalizing their inner monologue. Unless they show some recognition of how vapid they often sound, they tend to be difficult to spend time with.
A lack of self-awareness is one of the criticisms that caught up with Drake on his most recent album, Views. The album was difficult to listen to at points because even when the music was good, it was tough to get past how much Drake had begun to sound like a caricature of himself. Listeners would be vibing along to a song like "Child’s Play," but would have to stop midway through to think, “Is Drake really rapping about how his girlfriend borrowed his car to buy tampons from the store? Really?!”
Unfortunately, self-awareness—necessary as it is—runs directly at odds with the goal of being a cool rapper. Being truly cool requires effortlessness. Sustained self-awareness is anything but that. It requires one to question the merits of their actions, to second-guess their motivations, to constantly reckon with a feeling of discomfort. Sure, rappers can be cool in the new way of being cool, where they muster as much self-awareness as possible and attempt to be comfortable in their own skin, but this is a much more ambiguous type of cool. This is the type of cool that caused J. Cole to make a song like "Wet Dreamz"—a song about losing his virginity that was celebrated by some for its vulnerable and honest portrayal of the subject matter, but ridiculed by many more because J. Cole refers to his erection using the words, “Baby you done woke my lil' man up.”
Perhaps unsurprisingly, this newfound emphasis on self-awareness has made striving for the old type of coolness a fool’s errand. It’s impossible for audiences to look at a rapper who’s trying to emulate the casual je ne sais quoi of Biggie without wondering how much effort it must be taking to maintain this façade. It’s a problem that is compounded by the fact that rappers are now expected to be accessible on multiple platforms at all hours of the day. A$AP Rocky, for example—perhaps the closest thing I can think of to a modern rapper who is the old kind of cool—can’t maintain this persona indefinitely, because he has to deal with Charlamagne Tha God asking him to substantiate his under-researched views on the Black Lives Matter movement on live radio.
It leads me to wonder whether the coolness I’d perceived in the previous generation of rappers was genuine, or if it was simply a persona that would have crumbled under more scrutiny. Put under a microscope, Snoop Dogg has abandoned the effortless identity he once embodied in the past and has remained relevant by leaning into the era of overexposure. Any notion of him being cool went out the window when he signed the deal to make a television show with Martha Stewart and pander to White America. It’s simultaneously comforting and disconcerting to think that, if Biggie had lived long enough to be on Snapchat, I might just have learned that he was as lame as the rest of us.