In high school, you couldn’t tell me I wasn’t going to be a famous rapper. It was the mid-1990s, and the Wu-Tang Clan had recently dominated hip-hop with their unique blend of sullen street tales over obscure soul samples. My friends and I thought we were them; our rhymes were equally abstract. We’d often try to link with other crews to form one big collective. Back then, with my baggy jeans, oversized shirts and tan Timberland boots, I was the stereotypical rap head who prioritized intricate lyrics over the “Shiny Suit” ethos ushered in by Sean “Puff Daddy” Combs and his Bad Boy Records empire. He brought an era of decadence; from his finely tailored suits to the clean sound of his music, Combs found himself in the crosshairs of underground rappers with traditional mindsets, those who prioritized skill over flash.
I was very much in the traditionalist camp. I had grown up a fan of groups like De La Soul and Public Enemy, and solo acts like Rakim and Big Daddy Kane. While I could appreciate Bad Boy’s contributions to the culture — Brooklyn’s The Notorious B.I.G., perhaps the greatest rapper ever, was the label’s crown jewel — you were more likely to find me at the open-mic poetry slam than the massive arena show. Sometime in 1996, I was watching the music video channel when a song came on that I couldn’t ignore: “Body Rock,” featuring the rappers Tash (of the L.A. group Tha Alkaholiks); Q-Tip (of the famed trio A Tribe Called Quest); and Mos Def, the unassuming MC who I’d seen in a commercial with football great Deion Sanders a few years prior. Nothing about that commercial screamed “great rapper,” yet there he was in this video, rhyming alongside Tip and Tash over a midtempo electronic drum loop.
Mos was a student of De La, Tribe, and Jungle Brothers before them. He was a poet and a theatre kid who had a palpable affinity for jazz. Mos represented the full scope of Blackness, not just the overly aggressive trope depicted in the media. He seemed familiar, like the friends I rapped with. “Body Rock” was featured on Lyricist Lounge, Vol. 1, a double CD compilation of exceptional musicians — the poet Saul Williams; the rap group Company Flow; and the lyricist KRS-ONE, among others — but I was most intrigued with Mos Def’s contribution and wanted to see what he’d do next.
In 1999, he released his debut solo album, Black on Both Sides, via the burgeoning powerhouse label Rawkus Records. Just a year prior, he and fellow Brooklyn rapper Talib Kweli released their debut album as Black Star, the answer to what they saw as the gross commodification of hip-hop. Combs and the rapper Jay-Z were blamed for this; on “Children’s Story,” one of several highlights on Mos Def & Talib Kweli Are Black Star, Mos depicted Combs as a money-hungry culture vulture who merely wanted to line his pockets. By the rapper’s estimation, Combs didn’t want to add anything to the culture; wealth was the ultimate goal. Whether or not you were a Combs disciple, there was no denying Mos Def’s narrative flair. “Children’s Story” felt more like a conversation than a finger wag. It stoked even more interest in his solo work. He would not disappoint.
Black on Both Sides was a sonic and thematic masterpiece, rich with the tapestry of Afrobeat, ‘70s soul, punk-rock, ‘80s rap and Quiet Storm radio. Though ambitious, the execution led to a seamless listen that scanned as hip-hop and flared in so many different directions. There were elements of jazz, spoken-word and ambient, and the album’s lasting single, “Umi Says,” was a charming self-reflective take on his own wants and imperfections, sang in unpolished pitch over a velvet-smooth arrangement featuring an upstart composer named Will.I.Am and the great, yet unheralded, bandleader Weldon Irvine on keys.
Throughout the LP, Mos was funny and observant, blunt yet comforting. Even as he warned against wearing designer clothes in certain parts of Brooklyn, like he did on the song “Got,” he rapped with a figurative arm around your shoulder, as if to ask, “Are you sure you wanna wear that gold necklace in Bed-Stuy?” Elsewhere, on “Rock n Roll” and “Mr. N***a,” respectively, his tone was rightfully serious. On the former, he denounced Elvis Presley as an imitator who pirated the aesthetics of Black rock pioneers Chuck Berry and Little Richard. On the latter, he lamented traveling while Black (sidenote: my wife and I were subjected to a few microaggressions during a recent trip to London, so it’s a real thing). Undeterred, Mos ended the track by declaring life in the face of racism.
It took courage to release something like Black on Both Sides in 1999. Rap wasn’t as open-minded as it is now; for Mos to incorporate singing was still seen as peculiar. This was long before artists like Kid Cudi and Drake made singing rappers ubiquitous in the mainstream marketplace. He wasn’t the first to do this, though: Lauryn Hill did so on her 1998 opus, The Miseducation of Lauryn Hill, but she was an equally adept vocalist who held her own in R&B. The same went for Cee-Lo, who, as a member of Atlanta’s Goodie Mob in 1995, introduced himself as a remarkably talented rapper-singer, who’d go on to have a formidable career in hip-hop, soul and alternative rock. I don’t think Mos would’ve classified himself as a singer; he could carry a tune, but it wasn’t the strongest aspect of his artistry. Because hip-hop was still hyper-masculine, there was a false notion that Mos was perhaps too soft to be considered a serious MC. Where others rapped about drugs and violence, he showed us it was cool to be regular, that you could unpack life without the facade. It was fine to have a song about romantic love near one about the global water crisis. It was also fine to not have shit figured out.
I’ve always loved this album, but, as corny as it sounds, it didn’t truly click for me until I moved to Brooklyn in 2016. It’s one thing to absorb it elsewhere, it’s another to play it while walking through the same Fort Greene and Bed-Stuy streets that Mos trekked. I felt a semblance of the community that Mos felt, even though I was an outsider trying to navigate new terrain. Though I’d been a New York City regular long before I became a resident, Black on Both Sides made me feel like I belonged there. Just like the music I grew up with, this album reassured my stance as a person who likes many different genres. And because Mos was such a fascinating writer, he nudged me — indirectly — toward life as a full-time writer and journalist, a documenter of the culture in all its breadth and subtleties. Twenty-two years on, Black on Both Sides is a highly-regarded classic, a perfect album then, now and always.