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A Freewheeling Questlove Drops a New Hit with ‘Hip-Hop Is History’

With its deft layering of words, its samples, and how it articulates sound, Questlove’s Hip-Hop Is History is like De La Soul’s excellent album 3 Feet High and Rising.

Hip-Hop Is History
Questlove and Ben Greenman
June 2024

Questlove’s (Amir Thompson) newest (the eighth!) book, Hip-Hop Is History, with co-author Ben Greenman, is like a window looking deep into the workings of a pretty special hip-hop mind. Questlove is a bandleader/drummer, producer, social commentator, documentary filmmaker, and perhaps most importantly, a supreme music geek. He easily integrates all these perspectives into a book that is at once dense and freewheeling yet still clear and orderly. Style-wise, consider the deft layering of words, samples, and sounds of De La Soul’s 3 Feet High and Rising (1989). Hip-Hop Is History is entertaining and authoritative, coinciding with the genre’s 50th anniversary.

Since Questlove has been immersed in music and hip-hop in every way possible, what he conveys in Hip-Hop Is History is inseparable from his personal life and experiences. He writes that he was born into the music business with performer parents who took him on tour as a young child. By age eight, he was not simply aware of the top 40 but already knew all of the “engineers and rhythm arrangers” and “Commodores not named Richie.” From there, he was a hardcore rap fan as a kid. Then, of course, he had long-running success in his dynamic hip-hop group the Roots, who would also become the house band for The Tonight Show Starring Jimmy Fallon; he organized numerous special performances, concerts, and Grammy specials; and directed an Oscar-winning concert documentary, 2021’s Summer of Soul, to name a few of his creative accomplishments.

To give just one example of Questlove’s hip-hop life, one day in the early ’90s, he learns that the Roots landed their first record deal. He puts in his notice at his day job at Ruffhouse Records in Philadelphia, but before he leaves, he trains his replacement, Santi White, who will soon be a star in her own right as Santigold. Then he helps an up-and-coming band get a prime slot in a concert showcase: the future superstars, the Fugees. Talk about a single day in the life! So, Hip-Hop Is History‘s jacket is pretty spot on in declaring that this is a book that “only Questlove could write.”

For the book’s structure, Questlove notes that this is not an encyclopedia because it would have to be “fifty years long.” Instead, his way of keeping things focused is “less omission than mission.” He has a knack for navigating seemingly all of the most critical artists’ threads and trends, along with his many asides and excursions, across half a century. It’s obvious that Questlove had fun writing Hip-Hop Is History.

The author starts by deep diving into his earliest hip-hop/childhood memories: “Set course for ‘Planet Rock'”. From there, the book segments are chronological, mostly through ten eras, each covering about five years. Yet, his organizing system is nothing if not unique. In a rather unconventional approach, Questlove aligns each segment of Hip-Hop Is History with a musical trend, per se, but with the drug most associated with the rap music made at that time. He doesn’t write much about the drugs themselves, but the point is that certain drugs both strongly impacted and reflected the culture that the music came from in that era. Thus, in the mid-’80s, for example, there is a “forty-ouncer” (i.e., malt liquor) era (think: Darryl McDaniels of Run-DMC), then a crack era (e.g., gangsta rap acts), and a weed era (e.g., Dr. Dre’s The Chronic), and so on.

Questlove casually delivers some of these stories, sometimes through personal discussions and debates with longtime friends, such as Roots MC and band co-founder Tariq “Black Thought” Trotter. He relates valued and fresh insights into lesser-known artists, such as producers like Easy Mo Bee, and the better-known, like Kanye West. Questlove also regularly geeks out in Hip-Hop Is History, whether suddenly tracing music samples back across the years whenever he feels like it is interesting or giving his “overall recipe” for evaluating a rap song (20 percent each of “lyrics, samples, beats, production, and an MC’s performance”) or in breaking down every hip-hop record to receive a perfect 10 score from music site Pitchfork. It is all kept concise, and the reader’s flow rarely feels interrupted; co-author Greenlaw undoubtedly gets some credit here.

Questlove also gets personal to provide a wealth of meaningful observations and social context that is as humourous as it is poignant. As a kid, he befriends his local bully through the shared love of a new De La Soul single, “Buddy” (“That ‘Buddy’ shit!”). There is a moving, personal account of spending time with music producer J Dilla shortly before Dilla’s death at 32 from lupus complications in 2006 when Dilla was making what he knew would be his last record. Other times, Questlove identifies things like the uncle at the African American barbecue who picks the songs to “remind all present of his former cool”. He then notes that rappers EPMD perfected the same technique—”nostalgia, pure ego, pleasure”—in how they used samples.

If there is any quibble with Hip-Hop Is History, it’s that Questlove can be indulgent at times with somewhat obscure asides or in playing around with words and ideas that may be most interesting to him. However, this doesn’t get out of hand – it’s just part of the total package you get from a passionate music fanatic covering 50 years of hip-hop. As he was having fun writing this book, you will have fun reading it.

One anecdote illustrates Questlove’s truly unique perspective of hip-hop culture. The star Australian rapper Iggy Azalea has been under fire from some for possibly being a “flash in the pan” or, worse, a cultural appropriator. When she performed on TV with the Roots backing her, Questlove notes that she never looked back at the band or even acknowledged them. A lesser observer might have taken that personally and used it as an excuse to take an easy shot at Azaela. Questlove, though, understands it to be a defensive posture of someone under duress. He sees her in an insular, safe mode, literally not looking back, and he gets it. That sort of clarity and equilibrium makes him a special observer.

Also worth noting: despite Questlove being a part of the hip-hop fraternity, he doesn’t hesitate to criticize fairly and when appropriate. Thus, when he knocks an artist for presenting their music as authentic hip-hop—when clearly, they are aiming for commercial/pop success, he only needs to say: “Just say you were trying for a pop move.” Even the legendary Public Enemy, whom he loves, gets dinged for the song “Sophisticated Bitch“, on their 1987 debut album, Yo! Bum Rush the Show, for trying to be “edgy” but instead sounding “like your older brother trying his hand at rap.” Questlove is so knowledgeable and fair that it’s hard to imagine any of the artists in question being upset with his critiques. His critical observations increase the credibility and quality of Hip-Hop Is History.

Finally, the last chapter is, he says, written from “the future”, as if literally from the year 2073 at hip-hop’s 100th anniversary, e.g., referring to his real-life editor who always presses him on deadlines, “That guy’s long gone now, obviously. Good riddance, really.” At first, Questlove is having fun with this concept, and it is fun, though it could become a tacked-on, goofy idea for some readers. Still, the conceit provides the perspective and the depth needed to shift gears and land a less-is-more, spot-on summation of the genre that he and so many live and love.

Questlove is many things, though not your typical historian. In Hip-Hop is History, he uses his knowledge and experience to his advantage in every way, bringing unique and fresh perspectives. His well-honed instincts are spot-on. This makes for an immensely entertaining, if not indispensable, history of the most important musical genre of the last half-century. One can hardly wait to see what Questlove adds to his resume next.