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How Jay-Z’s ‘Vol. 3’ Explained Rap Music in 1999—and Predicted Its Future
In the fall of 1999, Def Jam posted a billboard atop the intersection of Flatbush and DeKalb avenues in downtown Brooklyn to advertise Jay-Z’s new album. Fittingly, the blown-up cover image for Vol. 3 … Life and Times of S. Carter depicted the rapper flanked by skyscrapers, peering downward. (Hov always did love a good metaphor.) He was now above the competition—in his home borough, in New York City, and in hip-hop. By the time Vol. 3 dropped in late December, Jay-Z was rap’s undisputed ruler.
Uneasy lies the head that wears the crown. Two of the previous kings of hip-hop had been slain: 2Pac in Las Vegas in September 1996, and the Notorious B.I.G. six months later in March 1997. The following year, chart-topping debuts from DMX and Lauryn Hill were game-changers; X released a second album at the end of ’98 that also went no. 1. Either he or Hill could reasonably claim the throne that year, but their reigns weren’t built to last. For all his bark, X was a little too one-dimensional to keep in step with rap’s evolution. Meanwhile, Hill’s first solo album would also be her last.
Into this power vacuum stepped Jay-Z, who had already built momentum from his own no. 1 album in ’98, Vol. 2 … Hard Knock Life. As the pall cast by the deaths of Pac and Biggie cleared, Jay snatched the crown in 1999. Vol. 3 went no. 1, as did all nine of his subsequent solo releases. Beyond his transcendent skill, Jay’s nimbleness and ambition would become the hallmarks of a long-running monarchy. He hewed his sound to adapt to radio trends and collaborated with the right people at the right time. And he was ruthlessly competitive, on and off the mic, which only added to his longevity.
While Vol. 3 isn’t regarded as Jay’s best album—that accolade is reserved for his debut or 2001’s The Blueprint—it does have a wide-ranging aesthetic that reveals the expansive kingdom that Jay-Z oversaw when he first assumed power. The South was rising. Dr. Dre returned. New disrupters were en route. And hip-hop in general was on the verge of going fully mainstream. Jay observed the terrain and adapted accordingly. From his very first words on the album—Yeah, I know you just ripped the packaging off your CD—to the bootlegged songs that were left off the final cut, Vol. 3 provides a perfect time capsule of rap as it headed into the new millennium.
Here, then, is a selection of songs from Vol. 3 that highlight where rap was 20 years ago and also where it was going.
“Watch Me” (feat. Dr. Dre)
Any residue from the East Coast vs. West Coast conflict was mostly gone by 1999—truthfully, the coastal rancor of the mid-’90s was always more of a Bad Boy vs. Death Row dispute. As those record labels waned, so too did any lingering beef. The deaths of Pac and Big set off an exodus of artists. Dr. Dre left Death Row in 1996 to start his own Aftermath Entertainment; two years later, Snoop Dogg fled to No Limit Records. In April ’99, Mase quit Bad Boy to become a pastor, and Sean “Puffy” Combs’s grip on radio playlists was loosening.
When the smoke cleared, Dr. Dre and Jay-Z emerged as the new leaders of their respective coasts—and, unlike their predecessors, willing collaborative partners. 1999 would be a huge year for Dre. In February, he hitched his wagon to a young white disrupter from Detroit, setting the stage for his second career as a record mogul. But not before dropping another smash of his own in November: 2001, his first solo album in seven years. As Dre’s new secret weapon, Eminem reprised Snoop’s breakout role on The Chronic with his own song-stealing performances on 2001. Track for track (and with apologies to Mos Def), it’s probably rap’s only undeniable classic from 1999.
Jay-Z had a hand in its success. He famously wrote Dre’s defiant comeback verses for “Still D.R.E.,” 2001’s lead single. For Jay-Z’s Vol. 3, Dre rapped the hook on “Watch Me” over a pounding Irv Gotti and Lil Rob beat that sounded like one of Dre’s, reusing Jay’s lines from an old Biggie song. It wasn’t an official East-West truce, but it felt like one.
“It’s Hot (Some Like It Hot)”
Speaking of disrupters: Eminem wasn’t the only ’99 newcomer who would one day dominate the charts with the assistance of Dr. Dre. For the Queens rapper named 50 Cent, however, the Dre partnership came a few years later. First was “How to Rob,” an opening salvo that wasn’t a mainstream hit, but featured lyrics—about robbing every big-name rapper or R&B singer—that instantly made 50 an industry villain. Jay-Z, of course, was one of 50’s many targets: “What, Jigga just sold like four milli, got something to live for / Don’t want a n-gga putting four through that Bentley coupe door.”
“How to Rob” served its purpose, as it drew the attention of rap’s new king. On “Hova Song (Intro),” Vol. 3’s opening track, Jay responded: “Mike Jordan of rap, outside Jay working / Now watch how quickly I drop 50.” Then, on the Timbaland-produced “It’s Hot,” he dropped the memorable dagger (which he premiered months before at Hot 97’s Summer Jam): “Go against Jigga your ass is dense / I’m about a dollar, what the fukk is 50 cents?” Two punch lines don’t constitute a real feud: Jay-Z saved his real missiles for a 2001 battle with someone closer to his level in Nas, who dropped two high-selling but mid-quality albums in 1999 and always remained a throne contender. As for 50? In 2000, he was the one who got shot up in a car. Three years later, alongside Em and Dre, he would rule commercial rap.
“Snoopy Track” (feat. Juvenile)
If 2001 was the most memorable rap album from 1999, then “Back That Azz Up” was the year’s most enduring rap song. It dropped as a single in February, after first appearing on Juvenile’s 1998 release 400 Degreez, which remains Cash Money Records’ best-selling album to this day. Off the strength of Juve’s “Back That Azz Up” and a string of lesser 1999 hits—B.G.’s “Bling Bling,” Hot Boys’ “We on Fire,” and a teenage Lil Wayne’s “Tha Block Is Hot”—Cash Money became the dominant force in Southern rap. The South had made inroads earlier in the decade, powered by collectives like Atlanta’s Dungeon Family and Memphis’s Hypnotize Minds, but New Orleans was the region’s epicenter in ’99, thanks to Cash Money and No Limit Records. The latter, however, was lauded more for the business exploits of its CEO, Master P, than for its musical output.
Cash Money’s breakthrough came with Juvenile’s 1998 single “Ha.” As the song started traveling beyond the South, Jay recorded his own verse over Mannie Fresh’s instrumental and sent it to Cash Money through its parent label, Universal. That unsolicited Jay verse was added to the official remix, and suddenly Juvenile was a bigger presence nationwide. The South may have been buzzing, but NYC was still the ultimate arbiter of rap cool. “After that,” said Juve of the remix in 2012, “I didn’t have a problem doing nothing with anybody. I didn’t have problems with all those companies who didn’t know who I was.” The “Ha” remix set off a chain of NYC-South team-ups in ’99, including the Ruff Ryders’ Juve-featuring “Down Bottom” and Cash Money’s appearance on Noreaga’s second solo album. (Jay-Z also popped up on a No Limit record—Silkk the Shocker’s “You Know What We Bout”—that went nowhere.) On Vol. 3’s “Snoopy Track,” Juve and Jay-Z reunited on a loopy, flow-driven Timbaland rhythm that began with the Brooklyn rapper paying homage to the South: “This is for my n-ggas down in Houston on candy paint / All my n-ggas in the Dirty South, Miami mayne / All my n-ggas in the ATL throwin’ dem ’bows.”
To be clear, Jay-Z giving Juve the coveted NYC cosign on “Ha” was less an act of benevolence than it was opportunism. From touring down South, Hov would’ve been aware of what local artists were popping in the clubs. His two songs with Juvenile, as well as his Vol. 3 smash “Big Pimpin’” with Texas duo UGK, were mutually beneficial collaborations. As Juve later put it: “When he did [the “Ha” remix], I was like, ‘OK, now I’m really in New York.’ For him it was the same way: ‘Now I’m really in the South.’”
Not for the last time, Jay identified a sonic wave to ride just as it was beginning to crest. In 2000, the Ruff Ryders and Cash Money would embark on a joint tour. By the mid-aughts, Cash Money’s Lil Wayne would stake his own claim to the king of rap title.

How Jay-Z’s ‘Vol. 3’ Explained Rap Music in 1999—and Predicted Its Future
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In the fall of 1999, Def Jam posted a billboard atop the intersection of Flatbush and DeKalb avenues in downtown Brooklyn to advertise Jay-Z’s new album. Fittingly, the blown-up cover image for Vol. 3 … Life and Times of S. Carter depicted the rapper flanked by skyscrapers, peering downward. (Hov always did love a good metaphor.) He was now above the competition—in his home borough, in New York City, and in hip-hop. By the time Vol. 3 dropped in late December, Jay-Z was rap’s undisputed ruler.
Uneasy lies the head that wears the crown. Two of the previous kings of hip-hop had been slain: 2Pac in Las Vegas in September 1996, and the Notorious B.I.G. six months later in March 1997. The following year, chart-topping debuts from DMX and Lauryn Hill were game-changers; X released a second album at the end of ’98 that also went no. 1. Either he or Hill could reasonably claim the throne that year, but their reigns weren’t built to last. For all his bark, X was a little too one-dimensional to keep in step with rap’s evolution. Meanwhile, Hill’s first solo album would also be her last.
Into this power vacuum stepped Jay-Z, who had already built momentum from his own no. 1 album in ’98, Vol. 2 … Hard Knock Life. As the pall cast by the deaths of Pac and Biggie cleared, Jay snatched the crown in 1999. Vol. 3 went no. 1, as did all nine of his subsequent solo releases. Beyond his transcendent skill, Jay’s nimbleness and ambition would become the hallmarks of a long-running monarchy. He hewed his sound to adapt to radio trends and collaborated with the right people at the right time. And he was ruthlessly competitive, on and off the mic, which only added to his longevity.
While Vol. 3 isn’t regarded as Jay’s best album—that accolade is reserved for his debut or 2001’s The Blueprint—it does have a wide-ranging aesthetic that reveals the expansive kingdom that Jay-Z oversaw when he first assumed power. The South was rising. Dr. Dre returned. New disrupters were en route. And hip-hop in general was on the verge of going fully mainstream. Jay observed the terrain and adapted accordingly. From his very first words on the album—Yeah, I know you just ripped the packaging off your CD—to the bootlegged songs that were left off the final cut, Vol. 3 provides a perfect time capsule of rap as it headed into the new millennium.
Here, then, is a selection of songs from Vol. 3 that highlight where rap was 20 years ago and also where it was going.
“Watch Me” (feat. Dr. Dre)
Any residue from the East Coast vs. West Coast conflict was mostly gone by 1999—truthfully, the coastal rancor of the mid-’90s was always more of a Bad Boy vs. Death Row dispute. As those record labels waned, so too did any lingering beef. The deaths of Pac and Big set off an exodus of artists. Dr. Dre left Death Row in 1996 to start his own Aftermath Entertainment; two years later, Snoop Dogg fled to No Limit Records. In April ’99, Mase quit Bad Boy to become a pastor, and Sean “Puffy” Combs’s grip on radio playlists was loosening.
When the smoke cleared, Dr. Dre and Jay-Z emerged as the new leaders of their respective coasts—and, unlike their predecessors, willing collaborative partners. 1999 would be a huge year for Dre. In February, he hitched his wagon to a young white disrupter from Detroit, setting the stage for his second career as a record mogul. But not before dropping another smash of his own in November: 2001, his first solo album in seven years. As Dre’s new secret weapon, Eminem reprised Snoop’s breakout role on The Chronic with his own song-stealing performances on 2001. Track for track (and with apologies to Mos Def), it’s probably rap’s only undeniable classic from 1999.
Jay-Z had a hand in its success. He famously wrote Dre’s defiant comeback verses for “Still D.R.E.,” 2001’s lead single. For Jay-Z’s Vol. 3, Dre rapped the hook on “Watch Me” over a pounding Irv Gotti and Lil Rob beat that sounded like one of Dre’s, reusing Jay’s lines from an old Biggie song. It wasn’t an official East-West truce, but it felt like one.
“It’s Hot (Some Like It Hot)”
Speaking of disrupters: Eminem wasn’t the only ’99 newcomer who would one day dominate the charts with the assistance of Dr. Dre. For the Queens rapper named 50 Cent, however, the Dre partnership came a few years later. First was “How to Rob,” an opening salvo that wasn’t a mainstream hit, but featured lyrics—about robbing every big-name rapper or R&B singer—that instantly made 50 an industry villain. Jay-Z, of course, was one of 50’s many targets: “What, Jigga just sold like four milli, got something to live for / Don’t want a n-gga putting four through that Bentley coupe door.”
“How to Rob” served its purpose, as it drew the attention of rap’s new king. On “Hova Song (Intro),” Vol. 3’s opening track, Jay responded: “Mike Jordan of rap, outside Jay working / Now watch how quickly I drop 50.” Then, on the Timbaland-produced “It’s Hot,” he dropped the memorable dagger (which he premiered months before at Hot 97’s Summer Jam): “Go against Jigga your ass is dense / I’m about a dollar, what the fukk is 50 cents?” Two punch lines don’t constitute a real feud: Jay-Z saved his real missiles for a 2001 battle with someone closer to his level in Nas, who dropped two high-selling but mid-quality albums in 1999 and always remained a throne contender. As for 50? In 2000, he was the one who got shot up in a car. Three years later, alongside Em and Dre, he would rule commercial rap.
“Snoopy Track” (feat. Juvenile)
If 2001 was the most memorable rap album from 1999, then “Back That Azz Up” was the year’s most enduring rap song. It dropped as a single in February, after first appearing on Juvenile’s 1998 release 400 Degreez, which remains Cash Money Records’ best-selling album to this day. Off the strength of Juve’s “Back That Azz Up” and a string of lesser 1999 hits—B.G.’s “Bling Bling,” Hot Boys’ “We on Fire,” and a teenage Lil Wayne’s “Tha Block Is Hot”—Cash Money became the dominant force in Southern rap. The South had made inroads earlier in the decade, powered by collectives like Atlanta’s Dungeon Family and Memphis’s Hypnotize Minds, but New Orleans was the region’s epicenter in ’99, thanks to Cash Money and No Limit Records. The latter, however, was lauded more for the business exploits of its CEO, Master P, than for its musical output.
Cash Money’s breakthrough came with Juvenile’s 1998 single “Ha.” As the song started traveling beyond the South, Jay recorded his own verse over Mannie Fresh’s instrumental and sent it to Cash Money through its parent label, Universal. That unsolicited Jay verse was added to the official remix, and suddenly Juvenile was a bigger presence nationwide. The South may have been buzzing, but NYC was still the ultimate arbiter of rap cool. “After that,” said Juve of the remix in 2012, “I didn’t have a problem doing nothing with anybody. I didn’t have problems with all those companies who didn’t know who I was.” The “Ha” remix set off a chain of NYC-South team-ups in ’99, including the Ruff Ryders’ Juve-featuring “Down Bottom” and Cash Money’s appearance on Noreaga’s second solo album. (Jay-Z also popped up on a No Limit record—Silkk the Shocker’s “You Know What We Bout”—that went nowhere.) On Vol. 3’s “Snoopy Track,” Juve and Jay-Z reunited on a loopy, flow-driven Timbaland rhythm that began with the Brooklyn rapper paying homage to the South: “This is for my n-ggas down in Houston on candy paint / All my n-ggas in the Dirty South, Miami mayne / All my n-ggas in the ATL throwin’ dem ’bows.”
To be clear, Jay-Z giving Juve the coveted NYC cosign on “Ha” was less an act of benevolence than it was opportunism. From touring down South, Hov would’ve been aware of what local artists were popping in the clubs. His two songs with Juvenile, as well as his Vol. 3 smash “Big Pimpin’” with Texas duo UGK, were mutually beneficial collaborations. As Juve later put it: “When he did [the “Ha” remix], I was like, ‘OK, now I’m really in New York.’ For him it was the same way: ‘Now I’m really in the South.’”
Not for the last time, Jay identified a sonic wave to ride just as it was beginning to crest. In 2000, the Ruff Ryders and Cash Money would embark on a joint tour. By the mid-aughts, Cash Money’s Lil Wayne would stake his own claim to the king of rap title.