Top Five, Dead or Alive

By Oliver WangFebruary 6, 2016

Top Five, Dead or Alive

The Rap Year Book by Shea Serrano

I SPENT MUCH of my 20s arguing over hip-hop; passionately, relentlessly, foolishly. What tracks were dope vs. wack. Which MCs were the most fly vs. weak. There were lists of songs, albums, artists, remixes, B-sides, guest appearances, ad infinitum, ad nauseam.

What animated most of these debates was the concept of “best.” Arguing over anything’s best-ness is easy; it merely demands an assertion of taste — and let’s just say that ’90s-era rap fans rarely lacked the desire to violently assert their tastes. Of course, this is also why “best” is a trap. As a criterion, it rests on ill-defined and often irreconcilable standards that yield few resolutions but a surfeit of altercations. 

I’d like to think I’ve aged out of such irascibility, yet I went into Shea Serrano’s new The Rap Year Book skeptical of its conceit: “The Most Important Rap Song From Every Year Since 1979.” However, as Serrano quickly establishes, arguing over what’s “important” is not the same as arguing over what’s “best.” To evaluate a song’s importance may also be subjective, but it demands some presentation of evidence. Importance suggests impact and influence and, therefore, forces a consideration of how we respond and react to music, not just individually but collectively and historically.

Rapper Ice-T, who wrote the book’s foreword, defines “importance” in a variety of ways: as “songs that are going to last,” as ones that “change the course of music,” as artists and recordings who carved “a lane” that, in turn, encouraged divergent branches to sprout from hip-hop’s tree of styles. Serrano himself clarifies the best vs. important distinction in his introduction, noting that in 1997, “Puffy’s ‘Can’t Hold Me Down’ wasn’t better than Biggie’s ‘Hypnotize’ […], but it was more important,” because it was Puffy’s first solo hit that then snowballed into a string of other massively successful Puffy projects over the next couple of years, and thus, it “plays an essential role in his legend, and his legend is essential to rap.”

None of this is airtight. You could counter that Puffy rode Biggie’s coattails to success (Serrano acknowledges as much). You could suggest that even if “Can’t Hold Me Down” hadn’t gone mega-multi-platinum, one of the better songs he worked on in 1997 — maybe “It’s All About the Benjamins” or “Mo Money Mo Problems” — would have triggered the avalanche instead.

I found myself mentally walking through these retorts and realized halfway through 1) this is fun to do and 2) maybe that reaction was part of Serrano’s intent. Unlike other hip-hop arguments I’ve been dragged into, he doesn’t browbeat his reader into agreement; he writes confidently but not condescendingly. More importantly, the main pleasure in reading The Rap Year Book isn’t in agreeing with Serrano’s choices but rather in following the elliptical paths he takes to explain them. 

Serrano rose to prominence on the recently shuttered sports/pop culture site, which was known for being insanely meticulous in its analyses yet unpretentiously loose in its prose. Drawing on both traditions, Serrano fills each chapter with tangents, footnotes, graphic charts, and “style maps” of lyrical analyses. He defines his approach in the 1985 chapter about Doug E. Fresh and Slick Rick’s “La Di Da Di”: “there’s straight-arrow information about the song […], there’s secondary color stuff that supports or buttresses the main idea […], and then, sometimes tucked away inside all of that and sometimes stated flat out in the open, there is the argument for why that song was chosen.”

That “secondary color stuff” takes many forms in the book, but it’s often the primary attraction. For example, in his 2001 chapter, Serrano chooses two songs as the most important: Jay Z’s laser-guided “Takeover” and Nas’s vicious rejoinder, “Ether.” Countless writers since 2001 have debated the “who won, Jay Z or Nas?” question, and if that’s all this chapter sought to address, then Serrano would simply be adding more noise. However, in exploring this historic battle, Serrano indulges no less than:

  • Three sidebars, one of which scans Jay Z’s “Dead Presidents” video for subtle hints to Jay’s relationship with his now-ex business partner, Dame Dash.

  • Seven rhetorical questions including “Which song is sonically better?” (Spoiler alert: Serrano says “Ether” because it was as “rotund as it was slicing.”)

  • Nine footnotes, of which number six suggests that the “Worst Nas Song” is not “Who Killed It?,” as is conventional wisdom, but rather “Braveheart Party,” which Serrano argues is “a failed grasp at radio play, and that’s way more offensive.”


It’s a deceptively controlled stream of consciousness, where Serrano’s seeming non sequiturs are as often as compelling, if not more so, than his central theses. As another example, for 1995, he picks Tupac’s “Dear Mama” as the year’s most important rap song. This happens to be a track I never cared for, then or now, and under other circumstances, I might have simply skipped the chapter, but I was drawn into Serrano’s discussion of Tupac’s unhinged performance in 1992’s Juice as well as his observations about the “Dear Mama” music video, including how it opens with three children playing a fictional board game called Thug Life (presumably not licensed by Milton Bradley).

Some readers might find these kinds of excursions distracting or indulgent. It’s not nearly as dense as David Foster Wallace at peak parenthetical, but it’s somewhere on the spectrum. Yet, though these may appear as “asides,” they provide a crucial, authorial glue that holds together a book built around 37 songs that may otherwise have very little to do with one another stylistically or historically.

After all, anyone can — and enough have — churned out annotated “best of” listicles, most of which don’t rise above naked clickbait to troll fans outraged that someone else’s enumerated opinions don’t align with their own. With The Rap Year Book, whether or not you agree with Serrano’s choices is immaterial; they’re simply an excuse for Serrano to take bathymetric dives into the crevices of hip-hop’s histories.

For all his roundabout writing, there are bursts of insightful, pithy prose in every chapter. Serrano suggests that 1992’s “Nuthin’ but a ‘G’ Thang” “took the anti-romance of gangsterdom and made it endearing, charming, almost insouciant.” For Drake’s 2009 “Best I Ever Had,” he observes that the Canadian rapper “commoditized the investigation of heartache,” while offering that in 1987, with “Paid in Full,” Rakim took “the very basic rap style that all of the first rappers were doing […] and then placed it in a super-missile and fired it toward irrelevance.”

In essence, Serrano plays both short and long cons with his arguments, and, as such, the least successful elements in the book are those that depart from his voice. That especially applies to the short “rebuttal” sidebars included in each chapter, where such invitees as film critic Wesley Morris and rock journalist Jessica Hopper make their case for a different “most important” rap song. These counters are well-intentioned, but tonally they often present a jarring shift from the rest of the book, especially as their authors have a mere 200 words to make their case compared to the pages in which Serrano’s ideas are allowed to unfurl. The Rap Year Book might ostensibly serve to inspire debate, but that doesn’t mean the book needs to actually document any.

Similarly, the various Style Maps, illustrated by Arturo Torres, sound intriguing on paper but are less so in practice. Seventeen songs have parts of their lyrics transcribed and marked with graphic icons, representing “aggression,” “introspection,” “boastfulness,” etc. Serrano writes that “the main function of a Style Map is always to look cool, but sometimes their other main function is to act as a reinforcement of the main point of a chapter.” Neither feels true, especially the second function. If you have to explain the importance of lyrics to a reader in visual fashion, it suggests either the lyricist was too obtuse or the reader is. 

Serrano previously created Bun B’s Rapper Coloring and Activity Book, so he understands the appeal and utility of literal illustrations. More successful than the Style Maps are the various one-off charts/graphs in different chapters. As an addendum to discussing Ice-T’s 1986 “6 in the Mornin’,” Serrano and Torres create a matrix chart of gangsta rappers, split between Intimidating, Cool, Approachable, and Ostentatious (and in turn, those rappers can be Iconic, Underappreciated, Overappreciated, and Perfectly Appreciated). The Geto Boys’s Bushwick Bill, for example, is the underappreciated and most ostentatious and intimidating of the two dozen MCs included. The 2003 version of 50 Cent is overappreciated but still most cool and approachable. Square in the middle of the matrix is the eternally underappreciated Schoolly D, presumably hip-hop’s ur-gangsta.

Not all the illustrations are meant to be so analytical. My favorite might be the Venn diagram in the 1992 chapter on Dr. Dre’s “Nuthin’ but a ‘G’ Thang” with one circle representing Compton and the other Long Beach. The intersection between them? “Trouble.” 

At its best, The Rap Year Book bears a strong resemblance to 1999’s Book of Rap Lists, written by the team behind the lauded rap rag ego trip, a.k.a. “the arrogant voice of musical truth.” That book was comprised of 400 lists split into 25 chapters, balancing between the essential (“Greatest Emcees of All Time”), the esoteric (“Hip-Hop’s Greatest Sweater References of All Time”), and the absurd (“8 Songs About Body Odor”). The Book of Rap Lists was deeply funny but also deeply heartfelt in reflecting the obsessive qualities that hip-hop fandom often inspires. In that respect, The Rap Year Book and the Book of Rap Lists are clearly close kin, albeit once removed.

Those intervening 15 years highlight a curious void in the publishing world. In that time, there’s been a stream of rap-related books, but most have taken familiar, conventional approaches: artist memoirs, linear musical histories, and regional scene primers written by journalists and academics. Far less common are witty, insightful, and playfully nerdy tomes such as those by Serrano and the ego trip squad. I take nothing away from the talents of those authors in suggesting that the field is ripe for other writers to contribute. 

Clearly, the audience is out there — Serrano’s book has led sales in Amazon’s “Music History & Criticism” category for weeks now — but I wonder if there’s still that bias that hip-hop is “too niche,” despite the avalanche of evidence to the contrary. Maybe that’s where these books are forever meant to reside: deconstructing our cultural centers by rapping from the margins.


Oliver Wang is the author of a book on Filipino American mobile DJs entitled Legions of Boom.

LARB Contributor

Oliver Wang is a professor of sociology at CSU Long Beach and a frequent writer on arts, culture, and the city. He has lived in the San Gabriel Valley for 20 cumulative years.


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