1999 Rewind: Remembering Mos Def’s Black on Both Sides

Are y’all ready to party like it’s 1999? We all love the 90s here at Soul In Stereo, so it’s only right to revisit albums that are marking 25 years in 2024. 1999 Rewind looks back at all your old faves and see how well they hold up.

Twenty-five years ago today, hip-hop received a true gift – the debut album of Yasiin Bey, formerly known as Mos Def. Black on Both Sides would go on to become a critical darling, and a daring departure from rap’s obsession with excess in the late 90s. We’re joined by my forever homie Brandon O’Sullivan – we call him THEO – of Shatterthestandards.com to talk about Mos’ best work to date.

Share your thoughts of first hearing this album.

Brandon: Reflecting on my younger days, I recall hearing these tracks at home, especially out on the patio. The beat on “Speed Law” still gets me moving even today. Over the years, as I grew up, “UMI Says” started popping up in commercials, which seems odd now, given the record label it came from. As a kid, I wasn’t focusing on the lyrics, but over time, I began to appreciate the themes of race, politics, water rights, Black life, and more. It’s a timeless record, and Mos Def was truly unique. While he didn’t originate these subjects, the way he constructed the album and his experimental approach to rap set it apart from what others were doing at the time.

Edd: Like Donell Jones’ Where I Wanna Be, I can’t say that I rushed out to cop Black on Both Sides on release day. “UMI Says” and to a lesser extent “Ms. Fat Booty” got a little radio play in my area and I enjoyed both but it wasn’t enough to push me to cop the album. But shout out to my homie and fellow music junkie Desiree for insisting that I hear this album. She bought it for me and she wasn’t wrong – it lived up to the hype. It was the center that hip-hop needed at the time, the calm balance between rap’s obsession with excess and its penchant for street justice and violence.

What’s Black on Both Sides’ best song?

Brandon: “Got”

You want to talk about a song that flawlessly aged the best. Mos delivers a cautionary tale about the perils of gun violence, the commodification of culture, and flaunting wealth and status, especially in environments where such displays can invite danger and violence, as you can tell how many rappers we’ve lost because of that. The song is a critique of materialism and a pearl of street-level wisdom about survival, humility, and the pitfalls of fame in the hip-hop community and society at large. “Got” abridges what Black On Both Sides stands for: insightful commentary, a return to hip-hop’s roots of storytelling and social critique, and a showcase of Mos Def’s skills as a top-tier lyricist and a cultural commentator.

Edd: “Ms. Fat Booty”

I know it feels like the safe pick, but it’s the right pick. Mos’ storytelling skills were in peak form as he details the initial encounter, hookup and dissolving of a relationship in less than four minutes. The soulful production adds to the atmosphere while Mos lays out his lyrical script like a Academy Award winning film director. And the twist ending got a chuckle out of me for years.

Which song features the best production?

Brandon: “Ms. Fat Booty”

Ayatollah’s sampling of Aretha’s “One Step Ahead” keeps playing in my mind. He crafts the sample to retain the original’s soulfulness while introducing a hip- hop edge. The beat possesses a relaxed yet infectious groove that perfectly complements Mos Def’s storytelling flow. Artists like JID later mirrored this approach with “Surround Sound.”

Edd: “Ms. Fat Booty”

Theo knows what he’s talking about. This album is more known for top-tier lyricism than it is for bangin’ beats. But the now-iconic Aretha sample is the perfect backdrop for the Mighty Mos’ ill-fated love story. And yes, the fact that artists as recently as a couple of years ago have copied this blueprint (hi, JID) shows how impactful it has become.

What’s the most underrated song on the album?

Brandon: “New World Water”

“New World Water” tackles environmental and social issues related to water—a subject rarely addressed in hip-hop back then. The focus on water rights, pollution, and the commodification of natural resources was ahead of its time. This made it less relatable or immediately appealing compared to tracks with more conventional hip-hop themes, which explains why it often gets overlooked —props to Psycho Les from the Beatnuts for the beat.

Edd: “New World Water”

As I write this, many of my friends in Florida are coping with the devastation of hurricanes (stay safe, Brandon) and it makes the message of “New World Water” hit so hard. While on the surface this track is about how water both nourishes and devastates humanity, if you look deeper it’s also a slick narrative on modern politics – again, a timely reference as we’re just a month away from a presidential election. It’s an incredibly deep track, no pun intended.

Which song should have been a single?

Brandon: “Know That”

While “Climb” is an obvious choice, we’ve already seen that type of single treatment with “UMI Says.” Instead, my pick is “Know That” because of the chemistry between Mos Def and Talib from their Black Star and Lyricist Lounge days.

Edd: “Know That”

Sheesh, Theo is three for three! Honestly I’m surprised he picked this one since it ranked so low on his list but I won’t hold that against him because he’s absolutely right about it being single-worthy. The album’s best-known singles are pretty soulful and lowkey, so Mos could have used a banger for the hip-hop heads. “Know That” fit the bill perfectly, especially since it reunites the beloved Black Star duo.

Which artist went hardest with the best feature?

Brandon: Busta Rhymes on “Do It Now”

One might assume I’d choose Talib, but his feature didn’t particularly impress me. Instead, I’ve got to give it to Busta Rhymes. Mos and Busta have distinctly different styles—Mos brings a laid-back, thoughtful, and poetic vibe, while Busta is known for his rapid-fire delivery, energetic performance, and charismatic presence. Their collaboration on “Do It Now” showcased a dynamic contrast that enriched the track. They played off each other’s strengths, with Busta’s verse injecting a burst of intensity that contrasted yet harmonized with Mos Def’s smoother narrative style.

Edd: Busta Rhymes on “Do It Now”

I liked Talib’s verse a lot more than Brandon did. “Intellectual property I got the title and the deed” will always be a dope line to me. But I agree that Busta outshines Talib, mainly because he’s so different from Talib and Mos while simultaneously fitting right in. 1999 Busta was an ABSOLUTE MADMAN but as Theo mentioned, never goes completely off the rails, He compliments without overpowering – the mark of a true pro.

This very thoughtful album dropped during the ‘bling era’ of rap excess. Did that negatively impact it, meaning it was overlooked, or positively impact it, meaning it helped this album to stand out?

Brandon: Looking back, 1999 was an unusual year for rap, with a noticeable dip in quality compared to the preceding years, as I noted previously. The release of this album came at a time when No Limit was declining, and Cash Money Records was on the rise. It wasn’t drastically different from what was out there with albums like this, especially within Rawkus Records, aside from “Ms. Fat Booty” and “UMI Says” making waves. During the ‘bling era,’ marked by conspicuous consumption and commercialism in hip-hop, Black On Both Sides distinguished itself through its clear divergence. The album emphasized sociopolitical awareness, incorporated live instrumentation, and delivered profound lyricism, offering a substantive counterpoint to themes of affluence and opulence. It didn’t gain immediate traction (unless you were in underground hip-hop circles), but word of mouth eventually got the album buzzing.

Edd: This sounds like a cheat, but the answer is both. In the late 90s, “conscious rap” often got a bad rap in the mainstream rap circles (sort of how “rappity rap” is decried today). It didn’t fit the mainstream mold and often was dismissed. That said, singles like “UMI Says” were able to break through and offer something new. For fans being fed a steady diet of “bling” and booties, Mos brought something much more appetizing to the table. It was different, and as I often preach today, different isn’t just good, it’s essential. It may have been overlooked a bit but its uniqueness gave it a lane that made it feel far ahead of its time.

Did Mos Def suffer from the “Thriller Curse,” meaning that because he was unable to top this album, fans underrated his later work?

Brandon: Mos Def didn’t suffer from a “curse” per se; rather, his solo discography isn’t the strongest. His later work delved into different themes and musical styles that might not have resonated with fans expecting something similar to Black on Both Sides. After his debut, he released The New Danger, which wasn’t well- received, and True Magic, a throwaway album to exit his Geffen deal. In 2009, he dropped The Ecstatic, which was a step in the right direction. I think it’s underrated (if he released it now, underground hip-hop fans might quickly label it AOTY). Then, in 2016, he changed his name to Yasiin Bey and released December 99th, arguably the worst album of his career.

Edd: Only to a slight extent. Yes, Black on Both Sides is Mos’ best solo project BY FAR – it’s not even an argument. But if you don’t count the Black Star album (which in my eyes, is even better than this one) there’s not like you have a ton of great albums to choose from. To Brandon’s point, the “Thriller curse” (or “Illmatic curse” if you want to use a rap reference) exists when fans ignore an artist’s great works because they don’t measure up to THE GREATEST work. “Bad is aight, but it’s no Thriller.” “It Was Written and Stillmatic are aight, but they’re no Illmatic.” Nah playa, those albums are better than aight, they’re fantastic. They’re just not as magnificent as their predecessor.  In Mos’ case, his follow ups aren’t fantastic, they really are “just aight” – OK albums plagued by inconsistencies. I do think his career post Black on Both Sides is unfairly dismissed – there IS good stuff to be found – but nothing hits like the early days.

How would you rank Black on Both Sides among the best albums of the 1990s?

Brandon: When considering all genres of the ‘90s, the album’s rank might vary since it’s competing with landmark releases in rock, pop, R&B, and more. It might not always crack the top 10 but often secures a spot in broader discussions about the decade’s best due to its quality and influence. Personally, I’d place it in the top 50 or 60 across all genres from the ‘90s, and strictly within hip-hop, maybe in the top 30.

Edd: Confession – I really like Black on Both Sides and greatly appreciate what it brought to hip-hop in its era. That said, I never saw it as a top 10 or even top 20 release of the decade. That’s not a knock on the album, it’s indicative of just how STACKED the 90s were with great releases. If it dropped in the 2000s and for sure in the 2010s, it would be much higher on the list. It’s a top 50 album of the era easily, and while that might sound low, in a decade crammed with classic after classic after classic, I still think it’s a strong showing. It might not be the absolute best, but we needed an album as daring and thoughtful as Black on Both Sides in that era.

Whom did you agree with most, Brandon or Edd? Join us by talking Mos Def in the comments below.