“Something in the drums sounded…wrong.”

A recurring variation on a scene is sprinkled through the first few chapters of Dilla Time, the new biography of legendary Detroit hip-hop producer James Dewitt Yancey, Jr. (aka J Dilla or Jay Dee) by Dan Charnas, a journalist and NYU professor who, in his 2010 book The Big Payback, proved himself an essential chronicler of rap music. One character after another—many of them musical heavyweights, like The Roots drummer Questlove and Grammy-winning engineer Bob Power—hears Dilla’s music for the first time, and though struck by its ingenuity, remarks that something is off. The beat, each one notes, is out of sync with the music. The song is dragging. The productions seem filled with rhythmic errors. Yet, whatever is happening in Dilla’s swinging lurch gnaws at them—in a good way. Because if these were truly mistakes, how had this music so thoroughly seized their minds, spirits and asses?

As the book unfolds, Charnas argues that what these musical smarties recognized was nothing short of how a young producer advanced the rhythm of recorded music. But their initial reactions were shrouded in the traditional garb of canonized expertise and established expectations. At the beginning, they still perceived lapses, errors, sloppiness rather than a deliberate sabotage of previously held norms, innovations that would become cornerstones of Dilla’s legacy, and introduce a different mindset to how machine-music producers work with technology.

An entire history of innovations in recorded music could be told through the lens of so-called musical mistakes. Do they even exist? At the level of intention, are errors ever actually errors? Indeed, deviations from written compositions or original concepts are often necessary to the process of a personal interpretation, a one-time communication that adds a uniquely human musical color. (See: in-real-time, improvised aspects of jazz.) Dilla’s productions did this too, relying more on his characteristic feel than a pre-arranged system. Even technical amateurism, whether in the dexterity of individual performance or in the overall sound of a recording, has been found critically purposeful (see: the history of punk and lo-fi recording techniques). A DJ trainwrecking a mix is easy to spot, but what if that juxtaposition suddenly mutates into a passage of gorgeously mixed sounds, or the EQ’d machinations of the mixing board reveal a beauty hidden only moments earlier? Is a “musical mistake” simply hearing without context?

Dilla Time is constructed using a number of overlapping narratives. There is a short but potent chronicle of Detroit—how its cultural, technological and racist histories left the city’s fingerprints on the American Century’s psyche, not least through music. There is James Yancey’s messy, previously under-reported biography—the story of a tenacious studio rat from the Conant Gardens neighborhood growing into an immensely influential turn-of-the-century figure, before dying of a rare disease at age 32, and supernova-ing into a full-blown icon in his afterlife. Yet the tome’s greatest triumph is the fascinating overlap of the two, the story of why only Detroit could produce a figure like J Dilla, whose genius rested on a personal relationship with the technological tool of his trade (the Akai MPC-3000 drum machine), almost a contemporary bluesman’s response to generations of Black Americans laboring to the rhythm of car-making factories that were the Motor City’s stock in trade. (The book includes an especially wonderful grid illustration that Charnas and colleague Jeff Peretz use to visually short-hand Dilla’s beats, and which invokes the Detroit city map.)

In his lifetime, Dilla’s brief but extraordinarily prodigious career featured production work with such hip-hop and soul luminaries as A Tribe Called Quest, D’Angelo, The Roots and Erykah Badu, yet his legend was made as a musician’s musician. He is most celebrated for his role in inspiring D’Angelo’s classic 2000 album Voodoo, and as a member of the Soulquarians production team that helped create the “neo-soul” sound. It was James Yancey’s extraordinary ears that led him to reconsider a sample-based producer’s relationship with the manipulation of older recordings, and the role this rapport plays in creating new music. Rather than make beats out of obvious instrumental passages, drum breaks or basslines, he found odd snippets in the crevices of dusty records to construct full tracks from. Dilla Time provides numerous scenes of young James gamifying music-making in bootcamp-type competitions with members of his crew, and later with more famous adversaries, sharpening his listening and sample-chopping acumen. (Dig if you will how Dilla’s first “hit” production, The Pharcyde’s “Runnin’,” is made from a snippet of Luiz Bonfa’s acoustic guitar solo on “Saudade Vem Correndo,” one of Stan Getz’s lesser known jazz samba excursions.)

Another musician who deeply contemplated his “mistakes” was Philly stalwart, “DJ Jazzy Jeff” Townes. In the book, Jeff explains that while “everyone in hip-hop had heretofore been trying to…accommodate the machine’s time grid, because producers were focused on mining samples for their sounds…[Dilla] did the opposite: he bent the machine grid to accommodate his sample sources, because he was focused on using those samples for their rhythmic and harmonic feel.” (Listen to how three bars of horns lifted from deep inside Ahmad Jamaal’s “Swahililand” are married to echo and empty space that creates the hook on De La Soul’s “Stakes Is High.”) One “mistake” people were hearing was a result of Dilla’s disruption of listeners’ rhythmic expectations through a subversion (dare I say, “humanization”?) of the agreed-upon machinist matrix of hip-hop beats. This was, of course, no mistake at all, but a strategy towards a new rhythm feel, akin to how Midwestern music producers making Detroit techno and Chicago house also partnered with technology.

The recorded century is littered with stories of left turns—rhythmic, harmonic, tonal—initially revoked as mistakes, obscenities, “anti-music,” or just noise. “Duke Ellington added notes to chords that would have sounded ‘illegal’ to the European ear, and thus invented a new, American kind of harmony,” writes Charnas of the composer’s 1930s and ’40s orchestral textures, while placing Dilla within a longer timeline. “It happened again when [Thelonious] Monk jammed his hands onto the keyboard to bring forth the sounds of notes in between the ones that were actually there.” It kept happening when the likes of Ornette Coleman, Cecil Taylor, and their progeny alienated not simply Old World authorities but also America’s jazz establishment, by relinquishing aspects of accepted musical language altogether. Their notions of “freedom” may not have been quite as “free” as the critics pronounced; the ways such figures evolved improvised ensemble playing and composition were shaped by new systems and harmonic rules. But they certainly left behind old standards and expectations. Moreover, the music often called “free jazz,” with its extreme emotional pronouncements, laid bare the very notions of musical error and ideal: can you even tell when a mistake occurred if one of the music’s imperatives is to embrace uncertainty? Can perfection exist in such a reality?

By the early ’70s, DJs in the Bronx were making turntables move in reverse, inventing the bewildering roar of record scratches emanating from vinyl discs never meant to be played backwards. Until they were. Likewise, the echoes of ghosts and sub-bass frequencies that emerged from mixing boards and speakers in Jamaican studios were first considered uninvited interference, but then became crucial to the new worldbuilding known as “dub.” No single example better illustrates this vital era in ambitious yet accidental machine music than when young Chicagoans Nathaniel Pierre Jones (aka DJ Pierre) and Earl “Spanky” Smith, Jr. brought home a Roland TB-303 bass synthesizer in 1985, and fiddled with its settings until they pushed it past what any Japanese product designer expected this small piece of practice-accompaniment gear to be used for. Smith and Jones, who also comprised the house-music duo Phuture, drew forth an ominous, hyper-synthetic gurgle soon dubbed “acid,” and the era of Acid House began with Phuture’s single, “Acid Trax.” Perverting creative technology became key to the process of making the new music, provocations guided by curiosity, novelty and discovery, setting fire to the strictness of the rulebook.

Or ushering in its democratization. The rise of machine-related music-making stirred a reactionary hornet’s nest among the institutions protecting traditional notions of musicianship and composition—the conservatories who taught it, the academics and fourth estates guiding the critical discourse around it. To their ears, technology-driven and sample-based musical styles were abominations. In reality, it was classism and racism shaping these institutional perspectives: some artists push culture in new directions, while others make “mistakes.”  The pianist-composer Vijay Iyer recently raised a related point in his essay on the word "wild," writing that in the art world, it has tended to wrongly denote “absence of order, planning, care, or thought;” but as he also pointed out, the graffiti technique “wildstyle,” for example, was “born of careful planning, meticulous labor, and astonishing ingenuity.”

Dilla’s inebriated swing is now folded into the everyday language of popular music. Another recurring scene scattered throughout Charnas’ book exposes a wide range of individual musicians around the globe (Houston, Melbourne, London, São Paulo, Raleigh) discovering the producer’s music, leading to the quiet creation of an admiration society whose members separately heard his signals as potentialities rather than errors. A decade and a half after Dilla’s passing, they make up a not insignificant chapter of pop’s aesthetic braintrust: pianists Jason Moran and Rober Glasper, the funk band Hiatus Kayote and musician Thundercat, producers Ninth Wonder and Flying Lotus, string player/arranger Miguel Atwood-Ferguson, singer Anna Wise, DJs like Lefto and Waajeed and J Rocc, as well as James’ now legendary contemporaries. They arrived here because these artists were willing to take a chance on something that perhaps, at first, sounded wrong, that revealed itself on repeated spins. Because such artists found his singular records and sounds, and over time shaped them into something personal. Not unlike how young James Yancey developed his own process of picking and chopping music to idiosyncratic ends. But as anyone attuned to finding new music nowadays recognizes, the space for wrongness, chance or reinventive trial-and-error is dwindling in the age of streaming, algorithmic discovery, and commercial optimization.

Which brings us to one of the more dystopian questions that Dilla Time surfaces: what might the musical future look like when its supposed mistakes and proficiencies are based primarily on sets of data? What will you listen to when the masters of categorical thinking replace guiding concepts like genre, with amenity and vibe and app stickiness? Such notions breed habits rather than revelations, delivering nearly context-free musical consumption to your feed. The granular use of these numbers certainly reframes the view of what is a mistake and what is perfection. These numbers also breed a kind of lobotomized uniformity, burying the radicalism which invites individual artistic possibilities. Is it a coincidence that an increased rarity in fundamental creative shifts has been a side effect of music’s quantized, confrontation-free Internet and software age? And that the stories and sounds of our era mostly rot in sameness, rehashes of prior experiences, familiar POVs, software presets and game-hacks you can find YouTube tutorials on? As Dilla Time recalls, Yancey too distrusted how these tech possibilities might infringe on his art. When the producer upgraded his studio in 2001, he deliberately chose not to replace his trusty old MPC with the latest drum machine model, continuing instead to mine the esoteric nature of his aging gear. “I like to keep it limited,” he said.

For a world continuing its headlong, choices-heavy charge into constantly upgraded technology and content optimization, such self-imposed limits embody the new mistakes. For a few, the superhighway is an increasingly gridlocked treadmill, and choosing to lean into the mistake-filled path less taken is a kind of survivalist embrace of art and ideas in all their strange, human idiosyncrasies. A creative independence. It’s not a new argument. The DNA of punk (the philosophical stance of “anti,” not the stylized subculture) was determined by subverting through simplification, messy amateurity, even ugliness. Though, like its cousin hip-hop, it too got co-opted—prime examples of the gentrification of mistaking—its embrace of mistakes remains central to its timeless and revolutionary railing against society’s straitjacket.

Dilla’s time and feel was similarly a conscious creative choice, a decision to embrace alternative ideas about what music could be. And that, too, was a reflection of who he was: numerous interviewees in Charnas’ book mention that the so-called rhythmic “limp” his beats produced could be seen in Yancey’s own everyday stride.

Look around: Aren’t what previous generations’ power brokers dictated as errors turning out to be some pretty decent guides to a mindful development of the future? It seems like an irrational way of engaging the world, but it’s certainly no more surreal than what we’ve got. The virtue of Dan Charnas’ book isn’t merely to embed Dilla’s story in a deeper cultural context; it’s to point us toward those seeds in the culture which, though often thought not to bear useful fruit, offer a self-sustaining way out. Don’t walk away from Dilla Time infatuated with old mistakes that have proven not to be. Go find some new musical mistakes that aren’t. Listen closely. They’re out there. ♦