Why 1998 Was the Greatest Year of My Hip-Hop Lifetime

October 2024 · 8 minute read

For Billboard’s 1998 Week, VIBE’s Editor-in-Chief Datwon Thomas remembers what an amazing time 1998 was for hip-hop, with his own memories from his early days as an Associate Editor at the pivotal XXL Magazine.

The best year of the golden eras of hip-hop is often debated. Was it 1986, with the genre’s birthplace of New York in total dominance? Is 1994 the one, when the East and West coasts coexisted on the charts with quality tracks? Maybe it was 1996 when the South came to the table with some commercial heat? Those are all viable options, but I’d say the buck stops at 1998. That was the culture shift year when all of the styles from different regions of the United States put in work to lift the then 20-something-year-old music category to the mainstream market to stay.

When I think of 1998, I automatically go to the tense times we had just overcome in the culture. It was the first full year we were without the superstars of the previous five years of growth in Tupac and The Notorious B.I.G (both killed, in 1996 and 1997, respectively). Their murders hit a hard reset in the timeline of B.T. and A.B. (Before Tupac and After Biggie). Thus, 1998 became the clean slate for the music that was slowly taking a rightful seat at the mainstream’s biggest table. Emerging from the grimy grips of the previous year’s dark battles and street-hop edge, we had flossy torchbearers in Diddy’s (known as Puff Daddy back then) Bad Boy Entertainment, a ghetto-fab, du-rag-and-mink-wearing Jay-Z of the mighty Roc-A-Fella Records and the definition of hood rich-turned-wealthy in the deep south’s Master P and his No Limit Records.

With hip-hop plotting its course for world dominance, R&B still had a stranglehold on urban music, especially on the radio. The singular Aaliayh dropped the sultry “Are You That Somebody,” stars Brandy and Monica teamed up for the world-stopping “The Boy Is Mine” duet, and Destiny’s Child (featuring a 16-year-old Beyoncé!) blasted on the scene loudly whispering, “No, No, No.” Yet, beyond the fanfare of how much the lane had opened for hip-hop, 1998 provided a level playing field where a street-hop artist like Queens, NY’s Mic Geronimo could switch from a rugged sounding “Shit’s Real” in 1994, to the glossy glare of uptempo grooves like his highest-charting single to date, “Nothing Move But The Money.” The jiggy-fied bright lights and shiny suits, paired with sexy female dancers, defined the time as one where reinvention to the pop-friendly side of the music could get you more looks.

However, what makes 1998 great is that the hip-hop nation was still in a tug of war with itself. For every flossy and bossy Jay-Z success story, you had a growling and gutter Yonkers, NY-reppin’ DMX (who famously dropped two Billboard No. 1 albums in the same year — with his first two albums) to match him up with. The balance of types of hype were all around. The climate would go from Onyx screaming on “React” to ATL’s Outkast flipping lines on “Rosa Parks” in a click of the remote, from the cable call-in request channel The Box to BET’s daily music video show Rap City.

The battles to figure out what was happening in the face of changing times didn’t just stop at the music’s output. The surrounding elements that influenced the art form was switching up as well. My first-hand experience of becoming a full-time music editor for the hip-hop monthly magazine XXL offered me a national view of where things were headed. My travels in 1998 took me to Atlanta for the first time, as I soaked in the southern-fried funk of the annual “Freaknik” festival, where thousands of HBCU students from all over the country partied wherever there was open space.

I’m talking all through the famous shopping center of Lenox Mall, while any highway that had pavement had women riding out the windows in scandalous-sized bikinis (with no beach in sight). And of course, the hottest dance spots of the time, like Club 112. Memphis, Tennessee’s Three 6 Mafia’s “Tear Da Club Up” ruled the speakers everywhere. Rappers mingled with fans freely. Minimal security, no social media and plenty of drinks kept the fun flowing. Oh, a couple of beat downs were handed out in the venues that would play “Tear Da Club Up.” I was a witness to this.

What I also saw in ‘98 was how crazy people would go when gathered together at popular NY club The Tunnel, which sat famously on the West Side Highway side of New York. You couldn’t go to the notoriously badass function that took place on Sunday nights if you were faint of heart. Meanwhile, you weren’t a top-tier rapper if you didn’t perform at the perpetually packed venue. Check out The Hip-Hop Nucleus: A Documentary on the Legendary Tunnel Nightclub of NYC on Itunes: It’s an excellent resource to give you the guts and glory of the storied events that went down, which included 50 Cent, Jay-Z, The LOX, Ruff Ryders, Snoop and Dr. Dre and LL Cool J.

Speaking of LL… man, his time in 1998 was insane. LL Cool J, then a seasoned vet of the verses and Canibus, the young hungry microphone mangler, had what was the biggest rap battle in ages. I had the pleasure of getting my first magazine cover story (XXL’s August 1998 issue) with the buzzworthy rookie rhyme wrecker in Canibus and boy, was it a turbulent time. (Let’s just say he and I didn’t see eye to eye for some of the story, among other things). Between “2nd Round K.O.” by ‘Bus and LL’s “The Ripper Strikes Back” the battle seemed like it wouldn’t stop, with career-ending bars of fury being tossed around like Planet Fitness kettlebells. Time and tales of what could have been of Canibus and Uncle L’s titan tussle leaves legend on who won bar for bar. Do your Googles on the lyrical fistfight, but like Tupac said, “I’ll let you tell it.”

Where we are in the game today, 20 years later, wouldn’t be half as important if not for the mixtape climate that DJ Clue, Kay Slay, Big Mike, Ron G, Doo Wop, and so many others created, which spawned the likes of Cam’ron and Dipset, Noreaga, Big Pun (already a star but still frequenting the underground circuit), Mobb Deep and so many others. This was a time when NY was as unified as it was divided. Crew love was damn near blood-bound, and the clique-ish groups in the five boroughs pumped out classic singles, like “Banned From TV” by N.O.R.E. and the never-ending flow of freestyles that now live on YouTube, but back then you could only hear if you could get your hand on one of the street heat compact discs.

Labels were flush with money flowing from overpriced CDs and vinyl pressings. Def Jam, Loud Records, Rawkus, Tommy Boy and others won big with releases that produced modern-day classics. That September 29 alone, there was a special release day that boasted Black Star’s Mos Def & Talib Kweli Are Black Star debut, Brand Nubian’s reunion project Foundation, Jay-Z’s mainstream breakthrough with Vol. 2…Hard Knock Life No Limit Records’ Mean Green compilation, Outkast’s third magnum opus Aquemini and The Love Movement, the announced swan song album for A Tribe Called Quest…#WhatATimeToBeAlive. This is all after Lauryn Hill dropped her genre-shifting Miseducation of Lauryn Hill debut solo album a few weeks earlier. A mega-competitive climate for great artists to be inspired by, and collab with for the future.

What really stands out for me in 1998 is one of the most memorable moments in my career and life with our XXL  “The Greatest Day In Hip-Hop” cover shoot. As a new magazine, just over a year old, our skeleton edit staff (with help from brother and sister publication staffs in Slam and Honey) and much-respected publicist, the late Leslie Smalls, set out to have the largest gathering of Hip-Hop acts ever. Over 270 rappers from all over the world converged on Harlem, NY on 126th street to recreate Esquire Magazine‘s iconic “A Great Day In Harlem” photo by Art Kane, where the legends of Jazz’s 1958 movement all smiled for history’s sake. To be a part of this monumental moment that hasn’t been duplicated in size and status since, where the likes of Rakim, Slick Rick, Mac 10, Fat Joe, Onyx, The Roots, Shaq, 3rd Bass, Goodie Mob, Scarface… so many stars of the moment and yesteryear arrived in full.

The mighty photography/filmmaker magic man of LIFE Magazine, Gordon Parks, took the rare shot under the pressure of impatient rap generals and industry elite. I happened to call Harlem resident and rap minister Big L on his cell in enough time for him to make the picture. Unfortunately, because President Clinton was in town, traffic was insane and the likes of Cormega and the reigning Queen of Hip-Hop, Lauryn Hill (who pulled up just as the huge group disbursed, visibly upset) just missed the shot.

I often wonder in this Insta-everything social media age if anything like those times will happen again. When you see how the long-standing tradition of beefs and battles like LL and Canibus are still going on today with Pusha T and Drake, how Big Pun’s surprising Latino mainstream success foreshadowed Cardi B’s white-hot stardom, where DMX’s total domination with tough-as-nails death blows have given way to the current devil-may-care attitude of these “Lil” everybodys and the irreverent talk and talent of Kanye West… I sit back and think, what will happen with the culture in the next 20 years? So much has changed since 1998, yet so much has stayed the same. Like JAY-Z and Beyoncé still ruling the world. From my viewpoint, they’ll still be our Hip-Hop Royal Family in 2038.

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