Why Yasiin Bey’s 'Black on Both Sides' is the Best Rawkus Records Album Ever Made

“I write a rhyme, sometimes won't finish for days / Scrutinize my literature from the large to the miniature.”

To be an MC — at least in the way expressed above — is an arduous and relentless endeavor. Even if you have the gift of gab as a lyricist, there’s still a discipline necessary to craft the words one envisions in their head, put pen to paper and articulate it as a piece of music.

Mos Def, now known as yasiin bey, set out to do exactly that — not just for the song he uttered these lines on, “Hip Hop,” but for 16 others that made up his debut album, 1999’s Black on Both Sides. Ambitious, eloquent and fun, bey would release this album on the storied Rawkus Records, the hip-hop label that released other beloved projects throughout the late ‘90s and 2000s, including Company Flow’s Funcrusher Plus, bey’s and Talib Kweli’s Mos Def & Talib Kweli Are Black Star, Pharoahe Monch’s Internal Affairs, Big L’s posthumous The Big Picture, Kweli’s Quality and Kool G Rap’s The Giancana Story.

But it’s primarily Rawkus’ ‘90s releases, specifically those mentioned, that aren’t just regarded as the label’s best, but some of the best hip-hop albums of the ‘90s. The common thread that connects them isn’t just the obvious of sharing the same label, but the passion for rap shared by each MC, and the expectation of the listener to tap in with them. Whether it be Funcrusher Plus or Internal Affairs, these bodies of work are exactly that: movie-length albums meant to challenge and reward listeners with lyrical wordplay that stood out then and now.

However, as great as they all are, bey’s Black on Both Sidesreigns supreme.

Even before the album came out, bey had already shown promise as the next guard of New York City hip-hop. A clear descendant of the Native Tongues side of ‘90s hip-hop, bey had been given De La Soul’s blessing, going bar-for-bar with his influences and peers on the group’s “Big Brother Beat” from 1996’s Stakes Is High. And two years later, he had his proper debut with Black Star.

In fellow Brooklyn MC Kweli, bey had found musical chemistry, and that’s evident on Black Star. The duo showed that they could have the lyrical dexterity of Company Flow’s El-P and Bigg Jus, exploring the joys and pains of Blackness — all soundtracked by production that would’ve felt right at home on A Tribe Called Quest album.

- YouTubewww.youtube.com

The album was impeccably — flawlessly — done: a project that proved bey and Kweli’s prowess as MCs. But it was clear that bey could do so much more than rap; as a couple songs showed — “Brown Skin Lady,” “Thieves in the Night” — he could even sing, showcasing an ear for melody that helped ground certain tracks with memorable hooks.

It’s this versatility that makes Black on Both Sides such a standout. Yes, everyone on Rawkus could rap. But bey wanted to do more than that — and he did.

The album’s beginning is a testament to this. He waits until Black on Both Sides’ second track, the aptly named “Hip Hop,” to offer fans the raps they were expecting as soon as they pressed play, and instead starts off with “Fear Not of Man,” a spoken word commentary on the state of hip-hop (and how its state is dependent on the people who participate in it) backed by a sample of Afrobeat pioneer Fela Kuti’s “Fear Not For Man.”

It’s a subversive introduction: a declaration where what bey is saying is more important than how he’s saying it.

“Mind over matter and soul before flesh” is a powerful, thought-provoking line, made all the better without a rhymeless line to accompany it. Actually, it punctuates two lines that rhyme together, hinting at how intentional bey was in making that bar stand out.

And then, the raps come.

“Hip Hop” is just as celebratory of the genre as it is critical of it. In the same song where he riffs off pioneering MC Spoonie Gee and shouts out his Native Tongues family tree, he calls out the commercialization of hip-hop, offering lines that linger in their unflinching honesty: “Hip-hop will simply amaze you, praise you, pay you / Do whatever you say do, but, black, it can't save you.”

And that type of sobering truth-telling isn’t just about the complexities of hip-hop becoming a profitable business. It’s directed at the pollution of natural resources we need (“New World Water”), the racial profiling Black people experience regardless of their fame or wealth (“Mr. Ni**a”) and the many, many, many struggles average Black people face in America (“Mathematics”).

What helps the medicine go down easy in songs like this is the production. The way DJ Premier splices together an unlikely fusion of sources — from The Fatback Band’s “Baby I’m-a Want You” to an Angela Davis interview — to create the booming swagger that is “Mathematics” is crucial to Bey’s lyrical onslaught.

Even on songs like “Umi Says,” it’s the beat that makes what bey is saying easier to digest, the artist self-producing the track alongside recording and mixing engineer David Kennedy, with contributions from the late Weldon Irvine on Hammond organ, and will.i.am (yes, you read that right) on electric piano. It’s Irvine’s organ that’s central to the instrumental though, his playing a baptism of musical waves that’s a pleasant contrast to bey’s poignant second verse.

The soundscapes throughout add to the versatility of Black on Both Sides. One moment, you have the Afrobeat-tinged “Fear Not of Man” that bey self-produced; the next, the psychedelic soul of The Bar-Kays’ “Memphis Sunrise” for “Rock N Roll,” which was produced by The Beatnuts’ Psycho Les.

In that variety, each song differs in feel, mood and tempo. And there was even one song in particular that embodied that variety in such a compelling way: “Brooklyn.”

Although Company Flow tried something similar on Funcrusher Plus’ “Tragedy of War (In III Parts)” to commendable but middling results, there really is no “Brooklyn” equivalent on any other Rawkus Records release. An ambitious soundscape crafted by Ge-ology, bey and Kennedy, “Brooklyn” is a three-part movement; a beat switch upon beat switch of near-flawless execution, where Milt Jackson’s “What Are You Doing the Rest of Your Life?” meets Roy Ayers’ “We Live In Brooklyn, Baby,” meets the Notorious B.I.G.’s “Who Shot Ya?”

“It came as a surprise to us that Yasiin wanted to merge the three different productions [on ‘Brooklyn’] into one composition, but you don’t question genius,” Kennedy said of “Brooklyn” in a 2019 Vice interview about Black on Both Sides. “I just followed Yasiin’s lead and made the edits.”

And bey is pacing himself throughout all of this as he honors his beloved borough. But just as challenging as it is, you can tell he’s having fun. Whether it be lyrical endurances like “Brooklyn” or more straightforward, pop-leaning tracks like “Ms. Fat Booty,” there’s no denying that he’s simply having fun rapping.

- YouTubewww.youtube.com

That these two songs can exist alongside a track where bey goes on a punk rock tangent (the end of “Rock N Roll”) or an album-ender that’s a rapl-ess instrumental jam morphed from Kool & the Gang and KC & the Sunshine Band samples, speaks to bey’s musical adaptability.

Not only could he give peak rap lyricism — offering rhymes that managed to be artful, efficient, and poignant — he could experiment both musically and lyrically, which is why Black on Both Sides is so distinct.

The rap dexterity of Funcrusher Plus is undeniably incredible, but at times it feels excessive, not just because of the several five-minute-plus tracks present throughout, but the overall dark and dour soundscape of the music. Internal Affairs shines in both its raps and varied production (what Diamond D did on the “Light” with that Wes Montgomery guitar sample is a brilliance comparable to Q-Tip and the late J Dilla sampling Joe Pass on “Let’s Ride”), but the album doesn’t quite recover from the booming rap-roundhouse-kick-to-the-dome that is “Simon Says.”

And Black Star, as practically perfect as it is, does more to define hip-hop more than it does redefine it.

Black on Both Sides achieved all of those things and more. In it, you could see the future: the genre-blending that would come with the Soulquarians, the Native Tongues-inspired collective bey was part of, but also so many left-of-center rappers, too — Andre 3000, Kanye West and Kendrick Lamar.

In its experimentation, inventiveness, playfulness and versatility, Black on Both Sides didn’t just care to be a great rap album; it wanted to be a great album — a project that honored bey’s past influences while signaling what hip-hop could be.

“It was my first record; I wasn’t certain I would get the opportunity to do it again,” bey told Highsnobiety in 2019. “So I just put it all out of my mind.”