“Black on Both Sides” by Mos Def
Hello! 😊👋
Welcome to a new edition of the Best Music of All Time newsletter!
Today’s music pick dives deep into one of the best rap albums from the genre’s golden era in advance of its 25th anniversary.
Genre: Hip-Hop, Alternative, Conscious Hip-Hop
Label: Rawkus
Release Date: October 12, 1999
Vibe: 💯
When older hip-hop heads pine for the genre’s “glory days,” a big part of the reason is this notion that it meant something.
Long before streaming numbers and online virality were the harbingers of success in the rap game, records many now identify as classics did more than sell—they shaped national conversation. Tupac Shakur’s solo debut, 2Pacalyse Now, and its documentary-style missives like “Brenda’s Got a Baby” led then Vice President Dan Quayle to proclaim there was “absolutely no reason for a record like this to be published." He called on Interscope to withdraw the record, like a restaurant taking an ill-prepared dish back to the kitchen. "It has no place in our society,” he added.
And yet, as the 90s progressed, it became clear that Chuck D had it right when he said, “Rap is black America’s TV station.” Flash forward to October 1999, the month Mos Def (now going by Yasiin Bey) dropped his iconic LP Black on Both Sides. Biggie and Pac were both dead, tragic collateral damage over hip-hop’s bloody regional dispute. As a result, once-proud labels like Bad Boy and Death Row were on life support, hemorrhaging cash and battling felony charges. In the process, hip-hop culture began to reject the excesses of the “shiny suit” era. More artists lent their voices to a growing contingent within the rap community who wanted to grow the genre more responsibly.
Bey explicitly calls out those views in this album’s opener, “Fear Not of Man.” In its dense first verse, he observes: “People talk about hip-hop like it's some giant livin' in the hillside/Comin' down to visit the townspeople.” Shortly after, he frames hip-hop as both a reflection and a driver of our cultural times. It’s uncanny how logically he breaks it down.
So the next time you ask yourself where hip-hop is going
Ask yourself: where am I going? How am I doing?
Till you get a clear idea
So if hip-hop is about the people
And the hip-hop won't get better until the people get better
Then how do people get better? (Hmm)
Well, from my understanding people get better
When they start to understand that they are valuable
Bey’s debut as a recording artist came the year before, as one half of Black Star alongside Talib Kweli. On “Definition,” the commercial centerpiece of that record, they named names (“They shot 2Pac and Biggie”) and cut through rap tropes that were wearing thin (”Too much violence in hip hop”). On “Thieves in the Night,” Mos turns this dissatisfaction into direct, dazzling bars, adding, “A lot of jokers out runnin' in place, chasin' the style/Be a lot goin' on beneath the empty smile.” That duality—acknowledging hip-hop’s pivotal role in growing black culture while also realizing it still has so much more to give—underpins Black on Both Sides. It’s what makes it matter.
Bey’s biggest strength as a writer and emcee is conveying vast amounts of sociopolitical context in a single bar or phrase. He excels at attaching broader historical meaning to assumptions made by anyone who turns a blind eye to what’s really been going on. On “Rock N Roll,” he seethes at the lack of acknowledgment artists like Chuck Berry and Little Richard get in the eponymous genre’s mostly whitewashed historical narrative. “Elvis Presley ain’t got no soul,” he surmises, before adding, “You may dig on the Rolling Stones/But they ain't come up with that style on they own.” The concept of white artists stealing from and profiting off the backs of marginalized groups is not a new narrative, but on this record, Bey’s observations are as incisive as they are inarguable at this point in history anyway. His words penetrate so deeply into the listener’s psyche without resorting to overt calls for aggression or violence, which is a testament to his power as a storyteller.
More impressive is “Hip Hop,” where Bey goes even harder over a retro Diamond D beat. “Hip Hop is prosecution evidence,” he spits, long before the term “Free Young Thug” became a trending activism conversation. “An out-of-court settlement, ad space for liquor,” he continues before painting a vivid picture of how the carrot can quickly become the stick in the context of the average African-American’s experience: “Choking the skyline, its low life getting tree-top high.” That one line packs such a punch that I racked my brain for examples of conscious hip-hop statements that bested or equaled its economy of prose in quite the same way. I couldn’t come up with any.
Bey isn’t the only creator firing on all cylinders here, either. He’s supported by a top-tier list of producers and on-mic cameos. Some of the names include DJ Premier, who nips at the heels of his “N.Y. State of Mind” beat from Illmatic, Ali Shaheed Muhammed and Q-Tip of A Tribe Called Quest fame, Ayatollah, who produced the monstrous instrumental for “Ms. Fat Booty,” and 88-Keys. The production choices are almost uniformly laid-back, which gives Bey and his carefully curated list of features ample room to flex their rhyming muscle. Similar to my note on the lyrics, to have the beats come across as too forceful or blunted would be a mistake. Bey’s not trying to run with the likes of Dre or G-funk’s elite. In a way, he’s actively positioning himself as an antithesis to that crowd.
One conversation that’s only gotten louder in recent years is that hip-hop is dying slowly. Sales are slumping, and many creative ideas come across as hollow reboots of something two or three decades old. As much as I dislike “the death of …” narratives, I think it has to do with risk aversion more than anything else. With the amount of mainstream pressure his commercial performances carry now, do you think Drake could suddenly pull back and release something akin to Black on Both Sides? I’d put the chances of that happening near that famous snowball in hell. But it’s that deep-rooted risk aversion that makes this record so special. Hip-hop is at its best when it takes chances and calls out the hypocrisy it sees from all angles. The willingness to stand out on the ledge pushes the boundaries of what most heads may deem “acceptable” or “real” hip-hop.
For something to be real, it has to matter, like this music clearly mattered so much to Bey as an expression of his truth. We need more of that energy in hip-hop.
👉 Don’t forget to click the album image to stream the album on your favorite platform 👈