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Earlier this month, Sean Combs threw himself a 50th-birthday bash at his Beverly Hills mansion, attended by such high-wattage stars as Kim Kardashian, Leonardo DiCaprio, Kanye West, Kevin Hart, Beyoncé and Jay-Z.


It was a world away from Jay-Z’s and Combs’ gritty days coming up in New York City — and from where the two were in the month of December 20 years ago. Back then, both found themselves in perilous positions that could have stalled their careers and legacies, and landed them in prison.


Combs’ arrest, on weapons and bribery charges in an incident that left three injured, was huge news at the time — made all the more scandalous because his glamorous then-girlfriend, Jennifer Lopez, was also arrested.


Meanwhile, the memory that Jay-Z stabbed a man has faded with time and his reinvention as a social-justice activist and one-half of the most influential couple in music, alongside wife Beyoncé.



“For Jay and Puff, [the arrests brought on] the decision of, ‘Am I going to shed the pretenses of the streets?’ ” said Dan Charnas, author of “The Big Payback.”


The two incidents also had a lasting societal impact: leading to an evolution in the NYPD and establishing the idea that rap was too big a money game to play in the streets anymore.


“In the ’90s, success in hip-hop was about artistic bragging rights and being the realest,” said industry expert Starr Rhett Rocque. “Now, success in hip-hop is, how mainstream can I go?”


The end of the century was a turning point for hip-hop, which was overtaking pop culture — from radio to fashion. In 1998, for the first time, the Bronx-born art form outpaced America’s then top-selling format, country. But as the industry grew more lucrative, artists seemingly still had something to prove.


“There was more money in hip-hop,” said Charnas. “Things started to change.”


The battle to stay on top and stay connected to the streets, where rap was born, led to confrontations with the law. For many artists, it wasn’t enough to write about the complexities of ’hood life. You had to live it.


In 1998, Busta Rhymes was arrested for possessing a loaded, unregistered pistol. The next year, DMX was booked after officers found a gun and drug paraphernalia at his Teaneck, NJ, home. Slick Rick and the Wu-Tang Clan’s ODB both did time at Rikers in the ’90s, while Suge Knight pleaded no contest to assault.


To some degree, violence wasn’t just accepted — it was expected.


On Dec. 2, 1999, Midtown’s Kit Kat Klub was packed with revelers celebrating rapper Q-Tip. Prince, Lil’ Kim and Eve were all on hand, as was the top player in the rap game, Jay-Z. The former drug dealer from Brooklyn’s projects-turned-Roc-A-Fella Records mogul was riding high on the chart-topping success of his album “Vol. 2… Hard Knock Life.” His first headlining tour had just become the highest-grossing hip-hop tour ever, pulling in $18 million.



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