What do Biggie Smalls, Kendrick Lamar, John Keats, Frank O’Hara, Milo and Earl Sweatshirt have in common? A hip-hop scholar drops some knowledge.

By Jeff Alessandrelli

When Kendrick Lamar won the 2018 Pulitzer Prize for Music earlier this year, for his 2017 album DAMN., it was big news: the first time the award had been given to a rapper or to someone who did not make classical or jazz music. It was also the first time hip-hop as a genre was given institutional recognition at such a high level. As numerous outlets noted, DAMN. was cited by the Pulitzer board as “a virtuosic song collection unified by its vernacular authenticity and rhythmic dynamism that offers affecting vignettes capturing the complexity of modern African-American life.” (Translation: It was real and it mattered. A lot).

“DNA” from DAMN.

Such a declaration is progress, but it’s also lofty-language particle upon lofty-language particle and the Pulitzer board’s statement inadvertently veils the breadth of DAMN.’s achievement. And that achievement, in my humble opinion, revolves around the primacy of narrative. DAMN. is a work that tells good stories in interesting, innovative ways, and those stories are why listeners—from the 11-year-old kid down the street who illegally downloaded Lamar’s album to the Pulitzer committee who, I assume, played it in high-def surround-sound in some type of pristine diamond-encrusted Pulitzer studio—embraced the album to the immense degree they did.

Being that I published a Notorious B.I.G.-focused book earlier this year on hip-hop, skateboarding and poetry, I’ve thought a lot in the past 12 months about narrative in hip-hop specifically and our current Western culture generally. In my aforementioned book, I wrote a long essay about the poetic and cultural similarities between Biggie and Frank O’Hara. Having written that piece, I came away with the realization that what I desire in a work of art—be it song, poem or other—is some sense of scope beyond the wholly authentic and wholly relatable. Meaning that I want a story that I myself can’t tell nor one that I can readily understand, at least not initially. Meaning that the more fractured and polarized we become as a society, the more I think powerful narratives assert themselves over all else and, for good or bad, whoever has the best words in the best order takes the cake, wins the prize, gets the gold, the guy, the girl.

These desires of mine might seem counterintuitive, especially when considering that notions of relatability (“they’re just like me”) and authenticity (“they’re telling it like it is”) seem to be at an all-time premium. But what often gets overlooked is how important the imagination—for both creator and consumer—is with regards to art and life.

When I listen to Richard Hell (Richard Meyers) or The Ramones (Jeffrey Hyman, Douglas Colvin, John Cummings and Tamás Erdélyi) or David Bowie (David Jones) or Iggy Pop (James Osterberg Jr.), I’m listening to characters that are simultaneously who they are and not; the names behind each “actual” person are constructions and, however steeped in real-life experience, the lyrics on the page and performances on stage by those performers serve to further the constructive façade.

The Romantic poet John Keats famously coined the phrase “negative capability,” which, as he put it in a letter to his brothers George and Tom in December 1817, involves “[a person being] capable of [existing] in uncertainties, Mysteries, doubts, without any irritable reaching after fact and reason.” Being “negatively capable” for the musician on stage and fan in the audience in the year 2018 simply means that you’re willing to believe the story because you want to believe the story, while knowing all the while that what you’re believing might not be entirely true. And that’s the allure.

When I listen to Richard Hell (Richard Meyers) or The Ramones (Jeffrey Hyman, Douglas Colvin, John Cummings and Tamás Erdélyi) or David Bowie (David Jones) or Iggy Pop (James Osterberg Jr.), I’m listening to characters that are simultaneously who they are and not…

As a hip-hop and poetry fan, my favorite rappers and writers are the type who, directly and indirectly, tell stories that are resolutely authentic while also being patently imaginative. A song like “I Got A Story To Tell” by Biggie contains a veneer of cold-hard-fact-truth (the fact that Christopher Wallace [aka The Notorious B.I.G./ Biggie Smalls] had sex with the girlfriend of a New York Knicks basketball player [reputedly Anthony Mason] while also being murkily false [the subsequent robbery of said New York Knicks basketball player which, no doubt, did not occur except in the song; it certainly was never reported on].

“I Got A Story to Tell” by the Notorious B.I.G.

Books like Lunch Poems by Frank O’Hara are still touted today because of O’Hara’s seeming insouciance and effortlessness—poems written off the cuff by the poet during his lunch breaks. But that truth is also a lie. Procrastination might have played some role, sure, but O’Hara took five years to complete the book and the work in it was anything but off the cuff; instead it was painstakingly measured and managed. The narratives encased within O’Hara’s Lunch Poems are true only to the extent that we as readers desire them to be. For 50+ years, then, such a desire has stayed intact.

O’Hara and The Notorious B.I.G. / Christopher Wallace being sadly deceased, however, there are plenty of contemporary hip-hop artists and poets who inhabit a place where what’s authentic shakes hands with what’s imagined. On his 2017 album Who Told You To Think?, the Chicago-born, Maine- and Wisconsin-raised rapper Milo (aka Rory Ferreira) raps “I’m back on my black Bukowski bullshit” on “Poet (Black Bean),” the opening track on the album, but I consider the rapper to be more the black John Ashbery. That is, from song to song, Milo’s frame of reference, diction and sense of self shifts, by design, in and out of focus. The stories that Milo tells on Who Told You To Think? are by turns revelatory and enigmatic.

“Poet (Black Bean)” by Milo, featuring James Baldwin:

“Landscaping” by Milo:

“Landscaping” finds the rapper quoting Whitman— “Bet my barbaric yawp’ll echo through the ages”—while acknowledging the fact that “we tenured in this deplorable reality” of crony capitalism and backdoor handshake greed. Other songs on Who Told You To Think? Low-key grapple with identity— “I don’t know my name, I don’t know my name/ I don’t need an identity to emcee/ I don’t need a passport to emcee/ I don’t need a license to emcee (from “IDK”)—and notions of ear candy/accessibility vs. innovation and allusive, analogy-driven wordplay—“Working title of my autobiography:/ I’m Probably Not the Rapper for You” (from “Take Advantage of the Naysayer”).

Full of discursions and tantalizing feints, Milo raps the way we—smartphones in hand—live. The narratives on Who Told You To Think? encapsulate that. They don’t begin/middle/end the way a 20th-century Notorious B.I.G. song does; they’re doing something different narratively because we’re all living very differently now as compared to when Biggie was rapping in the ‘90s.

While listening to Who Told You To Think? on repeat this long—long—winter, I was also reading two books of poetry, John Canaday’s Critical Assembly: Poems of the Manhattan Project (2017) and Tongo Eisen-Martin’s Heaven is All Goodbyes (2017). Critical Assembly is a work of poetry by way of historical fact and invention that, via persona-based lyricism, tells the story of the creation and testing of the first atomic bomb, with poems in the voices/persons of Albert Einstein, J. Robert Oppenheimer and Edward Teller (among many others). It’s a work to get lost in, one where, from poem to poem, story to story, all the reader is ultimately left with is, to quote from Canaday’s “Sources” epilogue, “the truth of fiction.”

By not being exact about things, by having to exist “in uncertainties, Mysteries, doubts, without any irritable reaching after fact and reason,” Critical Assembly is a book for our “truthiness” times. It feels authentic, full of the white and black of facts, while yet being larger and smaller than that. “The more we know, the less/ we feel” is how Albert Einstein puts it at the beginning of Canaday’s book and, right or wrong, there’s something to ponder there.

Full of discursions and tantalizing feints, Milo raps the way we—smartphones in hand—live.

For its part, Eisen-Martin’s Heaven Is All Goodbyes is a poetry collection that reads as carved in stone, deep-etched in euphonious granite. Refusing to be anything but multitudinous in the way that every single human that has ever existed was/is multitudinous, Heaven Is All Goodbyes serves to refute the concept of the insular “lyric I.” “When a drummer is present/ They are God. // “I am not an I. I am a black commons”’ is how the poem “I have to talk to myself differently now” begins. Those four lines are a mini-primer on how to read Eisen-Martin’s book. In it, sound is its own story and the collective is a voice that speaks in great cascades of I, every version different from the other. “I did right by the imaginary people that an american winter made/ real and then I made imaginary again” states one of the stanzas from “The Incense Is Me Smiling” and, snow still falling in mid-April, this stanza and Eisen-Martin’s book as a whole made (mysterious/uncertain/ comfortable) sense to me in a way that nothing else did this past winter.

Critical Assembly: Poems of the Manhattan Project and Heaven Is All Goodbyes are their own singular projects, works that don’t come around very often, but the ballpark that is Milo’s music is one that’s populated by a few other rappers, ones that rap in a way wholly authentic to our information-age-overload, scroll-centric times.”

Earl Sweatshirt’s acerbic, vehement I Don’t Like Shit, I Don’t Go Outside reminds me of Suicide if Alan Vega and Marty Rev didn’t like shit and didn’t go outside while also making beats, skateboarding and fangling out new sounds in a genre only found in their (Earl’s) heads (head).

An excerpt from Earl Sweatshirt:

Kool A.D.’s more buoyant string of albums 51, 19, and 63—named after Bay Area metro lines— are the sound of a 2018 Iggy Pop house party while Jim reminisces about his 1982 album Zombie Birdhouse and what might have been. I’m also partial to the hip-hop stylings of MIKE, Kamiyah, YG, and Open Mike Eagle. While being wildly different from one another, each embodies his/her own multiverse of sound, and the stories found in those verses are all authentic while being still more than so.

But getting back to Kendrick Lamar. “[A] virtuosic song collection unified by its vernacular authenticity and rhythmic dynamism that offers affecting vignettes capturing the complexity of modern African-American life” is how the Pulitzer board commended Lamar’s DAMN. As other commentators noted, the same could be said for a myriad of hip-hop albums past and present. What does makes DAMN. such a notable album, however, is the way it forces the listener to believe in an imagination that’s of reality and yet also beyond it. Its legitimacy is not merely beholden to one story, one mode, one singular existence or plane.

The same could be said for work by all the above hip-hop artists and poets. Beyond notions of direct authenticity and fact, how is more important than what. The further we move into the 21st century, such (conscious or subconscious) negative capability-focused tendencies will continue at the same pace.