Sean “Puffy” Combs was always willing to work for what he wanted, but always felt he deserved more than what he got. And so it was with Combs’ first record industry job as an intern and, shortly thereafter, a junior A&R man for Andre Harrell’s Uptown Records. Combs didn’t sign Mary J. Blige and Jodeci, but his break-laced remixes and fashion guidance updated Harrell’s New Jack Swing empire with the sound and look of Hip-Hop Soul.

Combs’ sense of entitlement was a blessing, a curse, and a blessing once more. While he became as much a star as his artists, garnering a 7000-word piece in VIBE, he bucked Harrell’s management decisions and was summarily fired for insubordination. Combs then used his notoriety to dazzle record executives at a number of major labels looking for a slice of the wunderkind’s magic.

Ultimately Combs was able to land a multi-million dollar deal with Clive Davis’s Arista Records on the strength of his salesmanship and his stable of two untested artists—Craig Mack and The Notorious B.I.G. When the two rappers quickly became commercial contenders, Combs’ became the model for a new breed of hip-hop mogul. Rap in the Death Row era had been about street muscle. Hip-hop in the Bad Boy era would be about style and celebrity as much as if not more than substance. An unfortunate development according to Combs’ detractors, but one as American as apple pie.

Also Watch