Despite the untimely deaths of icons Tupac and Biggie in 1996 and 1997 respectively, hip-hop was the late '90s.

The after effects of Bad Boy's "shiny suit" era as well as Def Jam's resurgence -- lead by Irv Gotti and superstars such as DMX, Jay Z and Ja Rule-- helped to calm the fear of fans who were unsure of where the genre was going musically, after the two tragic losses.

But while Bad Boy brought the polish and Def Jam introduced highly stylized grit another movement was emerging in the form of the traditionalist, artistic haven known as Rawkus Records. While the label featured a stable of talented artists with a number of landmark releases to their credit, the MC that many considered the crown jewel of Rawkus was Black Star member Mos Def.

Making a name for himself on the independent circuit before linking up with Talib Kweli for their 1998 album collaborative album as Blackstar, Mos Def's debut was highly anticipated amongst rap heads and he did not disappoint, delivering a bona fide classic and one of the more lauded records from that era. Featuring guest appearances from Busta Rhymes and Talib, among others, as well as production from the likes of DJ Premier, Ayatollah, A Tribe Called Quest's Ali Shaheed Muhammad and other elite boardsmen, the LP was a monster from start to finish, with the Brooklyn native giving the hip-hop community a collective eargasm.

While Mos, now known as Yasiin Bey, has gone on to produce a solid catalog (and 'The Ecstatic' does come close), 'Black on Both Sides,' released on Oct. 12, 1999, stands as the reason that listeners have still held out hope that Mos puts his acting on pause and deliver a classic to top 'Black on Both Sides' -- we all know he's capable of doing that.

To celebrate the 15th anniversary of this masterpiece, we thought it was only right to gather some respected names in hip-hop and get their thoughts and memories on the album.

  • 1

    Tony Touch

    DJ & Host of 'Toca Tuesdays' on Shade 45

    Favorite Memory Involving the Album:

    "Favorite memory involving the album was when we recorded Mos and Talib freestyle for '50 MC's Part 3' the same time the album dropped."

    Favorite Song on the Album:

    "Favorite song from the album is 'Ms Fat Booty.'"

    Favorite Beat on the Album:

    "Favorite beat on the album was 'Mathematics.' I was there when DJ Premier made it ... and Mos recorded it ... at D & D Studios."
  • 2

    Rob Markman

    MTV Rapfix & Sway in the Morning

    Favorite Memory Involving the Album:

    "My favorite memory involving 'Black on Both Sides' is the day that I bought it. I was working in a mail-room and had just enough money to buy the Mos CD and skipped eating lunch that day just so I could buy it. That's how bad I wanted the album."

    Favorite Song on the Album:

    "My favorite song on the album has to be 'Brooklyn.' Being from BK, Mos just captured home in a different way. Biggie, Jay nor Kane ever captured Brooklyn in that way. No knock to them, they're all legends and rep the borough fully, but Mos broke down the borough from an every man perspective."

    Favorite Beat on the Album:

    "My favorite beat on 'Black on Both Sides' is 'Ms. Fat Booty,' the track was the single for a reason. Ayatollah's knocking drums mixed with that Aretha Franklin sample was just perfect. That beat predates Kanye West's soul sampling and I'm sure influenced him on the come up. Just a dope track. "
  • 3


    Recording Artist (Foreign Exchange, Little Brother)

    What's Your Favorite Memory Involving the Album:

    "My favorite memory around that time has to be the cover of The Source that had Mos featured alongside Pharoahe Monch and Black Thought. The Rawkus movement was at its peak and that cover along with the release of Mos' album was really something special. It felt good to see my heroes get some shine."

    Favorite Song on the Album:

    "My favorite song on the album is probably 'Mathematics.' That last line "Why did one straw break the camel's back? / Here's the secret / A million other straws underneath it" has become one of my life's principles. You have to put everything that happens in life in its proper context and understand that nothing comes 'out of nowhere.' It's never the one straw that takes a person over the edge, it's a culmination of everything that came before it."

    Favorite Beat on the Album:

    My favorite beat is probably 'Love.' Those chords are so melancholy and unresolved. Plus, it's not very often you hear brushes on a hip hop record. Those are usually reserved for jazz.

    One Song You Wish You Could've Had A Guest Verse On and Why:

    "Me and my boys used to freestyle over the 'May December' instrumental back in college. In my mind it's like, "Yo I'D MURDER THAT BEAT!" But I know had Mos presented me with the opportunity back then, I woulda heard them pretty ass pianos and been like, 'Nah, man ... it's too beautiful! I don't wanna ruin it!' Lol."

    Ronna Gradus, Getty Images
  • 4

    Sonny Cheeba

    Recording Artist (Camp Lo)

    Favorite Memory Involving The Album:

    "My favorite thought about how 'Black on Both Sides' was how Mos came with harmony and a slick walk. The memory I got was the thought that here goes another slick dude adding his paint to the portrait!"

    Favorite Song on the Album:

    "One of my favorites is the 'Know That' joint with Talib... when Mos says 'F--- the Empire'."

    Favorite Beat on the Album:

    'Do It Now' with Busta is also a favorite. That beat was mean."
  • 5

    Robbie Ettleson

    Founder of Unkut.Com

    What's Your Favorite Memory of the Album:

    "I was just happy that I didn't have to sit through any more Talib Kweli raps after his horrible performance on the Black Star album. Cramming a thousand words into every bar does not make for good rapping."

    Favorite Song on the Album:

    "'Rock N Roll' since it upset a bunch of cracker-ass crackers with shots fired at Elvis, the Rolling Stones and Kenny G. OK maybe not so much the Kenny G slander."

    Favorite Beat on the Album:

    "'Ms. Fat Booty' was the stand-out track from that entire era and still gets the neck snapping to this day. Ayatollah smashed it on that one."
  • 6

    Peter Rosenberg

    Hot 97 Radio Personality

    Favorite Memory Involving the Album:

    "I remember the first time I heard my man DJ Book play 'Do It To Now' with Busta Rhymes. It was a b-side on the 'Ms. Fat Booty'/'Mathematics' promo. I was floored by how well Mos could go line for line with Busta. It really showed me just how special Mos is."

    Favorite Song From the Album:

    "It's so tough but its 'Hip Hop' or 'Umi Says.'"

    Favorite Beat On The Album:

  • 7

    Rah Digga

    Recording Artist

    What's Your Favorite Memory Involving The Album:

    "I was in Vancouver, Canada shooting '13 Ghosts' at the time and I must say it got me through a six-month period of not laying eyes on another black person [laughs]. It was also nice seeing a fellow Lyricist Lounge comrade doing big things."

    Favorite Song on the Album:

    "'Got' was my ish!!!! I was drawn to this joint cause I'm from Newark, N.J., and it was/is the carjacking capital of the world. No matter who you are or what you drive you gotta be on point when you come to complete stops. I used to be bumpin' that joint all awhile hoping I never get jacked."

    Favorite Beat On The Album and Why?

    "'Hip Hop' by Diamond D. That joint is hard body."

    One Song You Wish You Could've Had A Guest Verse On and Why?

    "That would have to be 'Hip Hop' because that would have just been a showcase of bars. 'Got' as a strong second. I could have easily turned that into a Brick City anthem [laughs]."

    Evan Agostini, Getty Images
  • 8

    Mikey Fresh &

    Favorite Memory Involving the Album:

    "My mother picking up the the CD off my night stand and asking: 'Mike, you're not black are you allowed to listen to this?'"

    Favorite Song on the Album:

    "'Umi Says' -- Mos was never afraid to experiment with his rap crooning, and this is him doing it at his best. Fifteen years later and every time I hear this song -- it feels like a moment."

    Favorite Beat on the Album:

    "'Ms. Fat Booty' -- Ayotollah bodied the Aretha Franklin samples. "
  • 9

    Paul Cantor

    Writer (Billboard, Medium, XXL)

    Favorite Memory Involving The Album:

    "I have a few favorite memories. One, I remember walking into a record store to buy the LP, and the white clerk giving me a sort of dirty look about it, and proceeding to make fun of 'Umi Says.' 'It's a good album,' he said. 'If you're into that conscious rap s---.' He put the word conscious in air quotes, indicating that even this early in his career, Mos was being typecast pretty heavily.

    Two, I remember, some time after the LP dropped, nominally dating a girl who knew the producer Ayatollah, the producer of 'Ms. Fat Booty,' and getting jealous that she was hanging with him when he got the call that the song had gone gold or something to that effect. 'That will be me getting that call one day' I told myself. 'And she'll think I'm cool.'

    Three, I remember the kids on my high school basketball team, many of them black, not really knowing who Mos Def was. They were into hip-hop, but something just didn't connect there. I think it was mostly because Mos Def didn't get any play on Hot 97. Like, if you didn't read rap magazines and hang out in downtown New York, you really had no idea who Mos was."

    Favorite Song On The Album:

    "'Do It Now' featuring Busta Rhymes. The back and forth exchange between Mos and Busta is probably one of the best ever captured on a hip-hop record. And that beat, so choppy and syncopated, it just moves. Next time you're in the car with friends, put it on, turn up the volume and just watch what happens. It is impossible to not find your neck snapping in precise movements with the beat. Perfection!"

    Favorite Beat on the Album:

    "'Know That' featuring Talib Kweli. I think when it comes to beats, I'm always more inclined to favor tracks that give me an immediate visceral reaction. In short, beats that don't require too much thinking on my behalf. 'Know That' was always one of those beats. It just has those hard marching-band drums, a clever not-obvious sample flip and a good groove. It's one of those beats you hear that makes you want to start rapping immediately."
  • 10

    Craig Jenkins

    Writer (Pitchfork, Complex)

    Favorite Memory Involving the Album:

    Fifteen years ago, I was 17 years old and kind of a bookworm, so I don't have any stories about fascinating events 'Black on Both Sides' soundtracked per se. One thing it did do for me at the time was present a genre-busting blueprint for left-of-center blackness that was crucial for me as a sorta weird inner city kid with a healthy contempt for late '90s commercial rap. Without getting cheesy 'Black on Both Sides' (and Black Star and Lauryn's [Hill's] 'Miseducation,' etc) was the record I needed at the time."

    Favorite Song on the Album:

    "I can't not say 'Know That.' Thirst for new Black Star has been a subplot in my rap fandom since Mos and Kweli first launched their solo careers, and 'Know That' was the first of what would turn out to be just a handful of official Black Star reunions over the years. (Lately I prefer 'History' off The Ecstatic, low key.) The beat is nails, and there's wild Star Wars references at the top of Mos' verse, which is hilarious now that I really sit and think about it."

    Favorite Beat on the Album:

    "I wouldn't call it a beat necessarily because there's so many live instruments holding it together, but 'Umi Says' is one of my favorite pieces of music in the bunch. I was deep in the throes of neo-soul by the time Mos dropped his solo debut, after Erykah and the Roots went supernova, and 'Umi Says' is kind of like the moment Mos' album steps up and takes its place in those ranks. Snatches me into the tower of my emotions every last time even today."
  • 11

    Al Shipley

    Writer (Baltimore City Paper, Rolling Stone, Complex, Noisey)

    What's Your Favorite Memory Involving the Album:

    "'The Black Star' album dropped in my junior year of high school and I played it around the clock for a year. But I was one of the only people in the world who liked Kweli's verses on that album more than Mos's. My brother and I would share albums and never buy the same thing, and if we both wanted to hear something, whoever was more interested would buy it, and I let him buy 'Black On Both Sides.' 'Ms. Fat Booty' just seemed like a cheesy single at the time, though it grew on me later. I'd fold my arms and act unimpressed, and to this day I like 'Train of Thought' more. But returning to 'Black on Both Sides' now, I didn't give it enough credit. The stylistic shifts work better than I thought they did at the time, and it's one of the few rap albums to really successfully pick up 'The Low End Theory''s trick of flipping every beat into the next beat with no dead air in between tracks."

    Favorite Song on the Album:

    '"New World Water' has always been a sleeper on that album and what he's saying on it is still relevant. But it's also just his choice of words, the way he attacks the subject from so many different angles. "

    Favorite Beat on the Album:

    "Mr. Khaliyl's beat for 'Do It Now' has always been the craziest beat, it's right in Busta's lane and sounds like it could've been on 'E.L.E.,' but it actually works in the context of Mos' album."
  • 12

    William Ketchum

    Writer (HipHopDX, Complex, Flint Journal)

    Favorite Memory Involving the Album:

    "This was the first 'conscious' rap album I bought. when I was first introduced to rap music, it was via the shiny suit era; I was a Bad Boy disciple and I loved Jay's 'Hard Knock Life.' A classmate suggested BOBS during my sophomore year of high school. I had seen Mos on lyricist lounge before, but I didn't really know his music.

    The main memory that I have from the album is really just being blown away that a rap like that existed. The depth of concepts, The awareness of himself and his community, it was all incredible to me. 'No Way Out' helped me cope with my mother's death because of the connection to Biggie's death, and the other stuff that I was listening to was fun, but 'BOBS' exposed me to the artful, societal aspect of rap. He also did so with the same type of energy that would go into any other type of rap. He wasn't boring or overly preachy, but he had conviction and purpose. I went back and got as much of the Rawkus catalog as possible after that.

    I went overseas with some of my classmates, and I got lost in the airport and separated from the group when we were supposed to come back. I panicked, but I was instantly calm after I put my headphones on and listened to "Habitat." In theme with the song, I actually felt at home. I also named my website after one of his lyrics from 'Hip Hop.' And 'Mr. N----' and 'Mathematics' were some of my first real introductions to racial inequality; I had seen it before in my own life, but I didn't really understand it. The album has really shaped who I am in a lot of ways."

    Favorite Song on the Album:

    "Too many to choose from man, seriously. When I first got the album, 'Mathematics' was my favorite because of the dedication to the theme and the scratches. But 'Hip Hop,' 'Mr. N----,' 'Got,' 'Brooklyn,' 'Ms. Fat Booty,' 'New World Water,' 'Fear Not of Man' and 'Habitat' have all taken the spot at one time or another. When I have listened to the album most recently, I tend to listen to Love the most. That beat just really soothes me, and the storytelling is dope."

    Favorite Beat on the Album:

    "First part of 'Brooklyn.' Gives me goosebumps. 'Love' and 'Hip Hop' are very close behind though."
  • 13

    Alvin "Aqua" Blanco

    Writer, Deputy Editor (

    Favorite Memory Involving the Album:

    "My favorite memory is just seeing Mos Def become a legitimate hip-hop superstar. I first noticed him as part of Urban Thermo Dynamics and thought he was nice, then saw him get his acting on via The Cosby Mysteries and get shine on De La Soul's Stakes Is High album. But my favorite work was the stuff on Rawkus (Universal Magnetic, If You Can Huh, Black Star). So to see him drop a full album that was dope from start to finish and made on his own terms was a beautiful thing."

    Favorite Song on the Album:

    My favorite cut is probably 'New World Water.' You would probably never guess that Psycho Les of the Beatnuts produced it and the lines: "'New World Water' make the tide rise high / Come inland and make your house go bye / Fools done upset the Old Man River, made him carry slave ships and fed him dead n----s." Slick talk and social commentary, few MCs do it this well."

    Favorite Beat on the Album:

    "Favorite beat is probably 'Umi Says.' Ever been to a party and the DJ throws that song on precisely the right time? That's why."