Taking Over for the '99: Cash Money, Aftermath and the Year Hip-Hop Set Up Its 21st Century Dominance

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Lauryn Hill in the press room at the 41st Annual Grammy Awards in Los Angeles on Feb. 24, 1999.

Following our Billboard staff-picked list of the 99 greatest songs of 1999, we're writing this week about some of the stories and trends that defined the year for us. Here, we look back at how the rap breakout stories from all over the country in 1999 helped set the stage for the genre to become popular music's dominant genre in the '00s and beyond.

In February 1999, a stunned 24-year old Lauryn Hill stood onstage at the annual Grammy Awards, clearly moved and shocked that she’d just taken the night’s biggest honor. “This is hip-hop,” she said in audible disbelief -- intimating that her acclaimed debut, The Miseducation of Lauryn Hill, taking home 5 honors that night was a cultural anomaly.

Up until that point, it certainly would’ve been. Rappers had been winning Grammys since the 1980s, and were nominated even before the introduction of rap-specific awards; but a famous boycott and a few forgettable wins over the course of the next ten years belied a dismissive view that the Academy had towards this “new” genre that broke through commercially 20 years earlier. It seems like hip-hop took the long way to the mainstream, but 1999 is a year when it was apparent that the music that was born in the Bronx was taking over in a way that has become undeniable since.

Somewhat by default, 1999 sets the stage for the 2000s; a generation that came of age with rappers centered in popular music really comes into full focus here. With the specter of the Death Row/Bad Boy beef having loomed a few years earlier, you now had an audience that had seen that drama tragically unfold under the glare of high-profile media coverage. Fans who would’ve had no clue who Tupac Shakur was in 1993 were now being introduced to hip-hop, as his legacy has been elevated to the game’s most revered folk hero. The Notorious B.I.G. achieved a similar deification; widely celebrated as hip-hop’s lyrical Hitchcock, and the man who’d re-established NYC rap’s preeminence back in 1994 with his platinum-selling debut Ready To Die. This new audience of rap fan wasn’t being introduced to the genre via poppy hits like “U Can’t Touch This” and “Bust A Move.” As Y2K dawned, the shift toward pop-friendly street rap had become the new normal.

On the heels of 2Pac and Biggie’s high-profile murders in 1996 and 1997, hip-hop had exploded as a mainstream force -- carried by the more R&B-friendly production approach and familiar 80s pop samples typified by those late stars respective labels in Death Row and Bad Boy. Bad Boy impresario Sean “Puffy” Combs released his multiplatinum No Way Out that summer, and it was followed by new label star Ma$e dropping his own hit debut Harlem World that fall. With the crossover emergence of southern rap powerhouse No Limit Records that year, the South leapfrogged the suddenly-shaky West Coast; and in 1998, DMX’s blockbuster debut It’s Dark and Hell Is Hot thrust hardcore East Coast rap onto the pop charts. By the end of that year, Brooklynite Jay-Z finally scored the kind of commercial success that had proven elusive for him over the previous three years -- via monster hits like “Can I Get A…” and “Hard Knock Life.”

The latter half of the 1990s had seen hip-hop’s pop ascendency shift; with grittier acts like DMX and Lil Kim becoming the kind of pop stars that had previously been the sole providence of “safer” acts like LL Cool J and Salt N Pepa in the earlier half of the decade. Legendary acts like N.W.A. and Public Enemy never hit the Top 40 during their classic runs; and it was unlikely that anyone in 1991 would have expected even an Ice Cube to be a radio fixture (Cube wouldn’t score a major pop hit until 1992s “It Was A Good Day”. But now that “gangsta” rappers could embrace R&B hooks without losing any semblance of credibility, artists like Big Pun could drop grimy and gritty album cuts, while letting shiny singles like “Still Not A Player” push them to platinum heights.

And the times were being defined by a wave of producers who’d pushed hip-hop onto the pop charts with hits that presented on their own terms, while being infectious enough to garner pop airplay. On the heels of rap’s most unapologetically slick years, Juvenile’s decade-capping dance floor anthem “Back Dat Azz Up” made few allowances to the Top 40 mainstays of late-'90s pop-rap, but became one of the era’s defining singles, peaking at No. 19 on the Billboard Hot 100 in November. Mannie Fresh’s stellar production took Cash Money Records to a level of visibility that seemed to eclipse fellow NOLA mainstay No Limit from the moment Juvie broke through, as the crossover ambitions of No Limit’s head honcho Master P had become increasingly obvious as that label embraced a southern brand of shiny suited sheen. Meanwhile, B.G. and future superstar Lil Wayne both dropped their own major label debuts in 1999, and suddenly Cash Money had taken over the airwaves with an approach that was equally glossy, but that retained just enough underground grit.

Even as Cash Money’s success -- along with the commercial rise of Miami acts like Trick Daddy and JT Money, and early ripples from a brash party rapper out of Atlanta named Ludacris -- further cemented the South’s transition from upstart to national force, the West Coast hadn’t completely faded in the wake of Death Row’s demise. The revitalized Dr. Dre suddenly had one of the hottest labels in hip-hop, after the blockbuster major debut of Eminem. Dre’s Aftermath Records initially struggled to escape the shadow of Suge Knight and Dre’s former label Death Row; but after Em’s Slim Shady LP became a runaway hit in the first half of ’99, Dre followed it with his own 2001; a slick and inspired West Coast call-to-arms that also seemed to reinvigorate former protégé Snoop Dogg -- who’d also defected Death Row to land on No Limit Records back in 1998. Snoop would also work with Dre for the first time in five years on No Limit Top Dogg, his second release for the label.

With a bigger audience consuming hip-hop than ever before, and with rappers now fully centered in pop culture, the commodification of hip-hop became a sore spot and talking point. Artists who’d been pillars as recently as 1995 were now viewed as has-beens as audiences only seemed to see them as preamble to the shiny pop stars that were now culturally ubiquitous. Acts like Mos Def seemed to present as an antidote to what had become the genre’s most unapologetically commercial era; his Black On Both Sides affirmed the promise he’d shown in Black Star with Talib Kweli, and connected Mos to artists like De La Soul and A Tribe Called Quest; like-minded veteran acts who’d helped to define the decade. Those latter acts were also in states of flux: Tribe’s Q-Tip was enjoying newfound solo success with crossover hit “Vivrant Thing” and De La wouldn’t release a new album until the 2000s.

Women in hip-hop had seen heightened visibility throughout the 1990s and as we neared Y2K, many were absolutely peaking as the industry veered into its most high-profile period. Along with Lauryn’s monumental 1998 and ‘99, other women in hip-hop were closing the decade on tremendously hot runs. Philly rhymer Eve broke big -- scoring two Top 40 Hot 100 hits from her platinum-selling debut album Let There Be Eve...Ruff Ryders First Lady. Missy Elliott was in the middle of a classic run, in ‘99 she released Da Real World and dropped her own monster hit in “Hot Boyz,” which shot all the way to No. 5 on the Hot 100 and topped Billboard's Hot Rap Singles listing for a record 18 weeks.

From hit albums like Ready To Die to headlines about an “East Coast/West Coast war,” the grimness of the mid-90s, both in terms of subject matter and real-life tragedy, was covered in often-exploitative ways, but that coverage seemed to serve as a catalyst for the rap game’s late 90s super-visibility. As the Internet became more crucial to how fans interacted and artists promoted, hip-hop would become even more culturally inescapable and hyper-commodified. As the 2000s dawned, even rappers who weren’t household names could earn platinum certifications. That momentum wouldn’t shift until the downloading revolution cut the legs out from under the traditional music industry sales model in the mid-’00s; but it helped to spawn the approach that would mint soon-to-be-stars like 50 Cent and Kanye West.

There’s an entire generation who only knows hip-hop as the undeniable force it’s been for the past 20 years. As the world awaited Y2K, hip-hop was enjoying the fruits of 25 years of creative, innovative art. The commercialization that had been obvious since Run-D.M.C. was now in full bloom and there would be no going back. Hip-hop wasn’t vying for space anymore -- it was setting the table. Mainstream R&B would become obscured by hip-hop over the next 20 years; young rock bands would become less widely relevant than their classic rock or even ‘90s alternative forebears -- and pop stars would become virtually joined-at-the-hip with rappers and rap aesthetics. Hip-hop defines a generation, and that takeover truly became undeniable, fittingly, at the dawn of the 21st century.