"This birthed gangsta rap," Questlove said. "N.W.A just took [its] formula and ran with it." The Philly MC got his track's name from a gang, Park Side Killers, and its beat from an evidently stressed-out Roland 909 drum machine. In a lazily menacing flow, he buys coke, beds a whore, buys weed and flashes a pistol. That he decides not to pull the trigger makes the jam no less chilling.

The Golden Age of HipHop !

In 1991, Bushwick Bill of the Geto Boys took a bullet – reportedly self-inflicted – in the eye during a suicidal freakout. He survived; a photo of the diminutive MC displaying his wound appeared on the Texas trio’s album cover. This Top 30 hit – a classic of cracked ghetto armor that put Houston hip-hop on the map – revealed even more of the manic depression and death wish inside their rhymes. Scarface, who wrote and produced the track, sounded like his movie namesake: fully armed at the edge of sanity, over dark-treble guitar and a gunslinger-walk rhythm sampled from an old Isaac Hayes tune. “It was an awesome, complex display of paranoia,” says Questlove. “It managed to add a third dimension [to Geto Boys’ sound], and it humanized them.”

Climbing to Number Two on the singles chart in early 1993, "Nuthin' But a 'G' Thang" made Dr. Dre the undisputed flag bearer of West Coast rap, while also ushering that genre into the pop mainstream. The song's secret weapon was a relatively unknown pup named Snoop Doggy Dogg, whose verses are packed with effortless quotables. The song also introduced Dre's masterful "G-Funk" style of production, which updated George Clinton's legacy with slow, rubbery funk and layered synth hooks. "We made records during the crack era, where everything was hyped up, sped up and zoned out," Chuck D explained. "Dre came with '?"G" Thang' and slowed the whole genre down. He took hip-hop from the crack era to the weed era."