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100 Greatest Hip-Hop Songs of All Time

What makes a great hip-hop song?

100 Greatest Hip-Hop Songs of All Time

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We asked 33 artists and experts – from Rick Rubin to Big Boi, Mike D to Chuck D – to vote for their favorite hip-hop songs.

100 Greatest Hip-Hop Songs of All Time

Mobb Deep, “Shook Ones (Part II)”

In the mid-Nineties, Mobb Deep came out of New York’s Queensbridge projects and boiled East Coast gangsta rap down to its rawest, nihilist essence. A suspense-amping snippet from a Quincy Jones soundtrack infuses the rumbling song with a sinister hiss, while background mumbles add shady menace. Prodigy, whose mother was a member of Sixties girl group the Crystals, promises that his “gunshots will make you levitate,” and makes sure to remind listeners that he’s “only 19.” Years later, you still ache for that kid.

100 Greatest Hip-Hop Songs of All Time

Schoolly D, “P.S.K. What Does It Mean?”

“This birthed gangsta rap,” Questlove said. “N.W.A just took this formula and ran with it.” The Philly rapper’s 1985 joint takes its name from a local gang, Park Side Killers, and its wicked “Sucker MCs”-style beats from an evidently stressed-out Roland 909 drum machine. In a lazily menacing flow, Schoolly buys coke, parties with a hooker, buys weed and goes to the club, where he finds an MC biting his style. “Put my pistol up against his head,” he matter-of-factly explains. That he decides not to pull the trigger makes the jam no less chilling.

100 Greatest Hip-Hop Songs of All Time

Jay Z, “99 Problems”

Rick Rubin hadn’t worked on a hip-hop project for years when Def Jam’s Lyor Cohen persuaded him to get in the studio with Jay Z. “I knew I was gonna get fresh shit,” Cohen recalled. He got one of the most explosive tracks ever, based around the gigantic drums from Billy Squier’s “The Big Beat.” Jay concocts an indelible pop chorus and sketches out a scene based on an encounter with a racist cop from his pre-stardom days. “The first offense wasn’t the crack in the ride but the color of the driver,” he wrote in his memoir.

100 Greatest Hip-Hop Songs of All Time

Kanye West, “Jesus Walks”

Kanye West has never been shy about his God complex, but humility, not hubris, drives hip-hop’s greatest gospel testimonial. The production is stirring – a church choir cresting above a martial beat – and West has a message to match, forsaking easy pieties to rap about internal struggle (“We at war with ourselves”) and self-doubt (“I want to talk to God, but I’m afraid because we ain’t spoke in so long”). The song helped solidify his own transcendent status: “I made ‘Jesus Walks,'” West rapped years later on “Otis.” “I’m never going to hell.”

100 Greatest Hip-Hop Songs of All Time

Nas, “N.Y. State of Mind”

No track better sums up Nas’ ability to spin dense, dazzlingly lucid verses. “N.Y. State of Mind,” a highlight of his hugely important 1994 debut, Illmatic, is no anthem or ode to the city. It’s a detailed narrative about a Gotham gunfight, delivered in a nearly 60-bar run that was later broken up to create a spellbinding track. “He did the whole first verse in one take,” recalled producer DJ Premier, who exactingly balanced two jazz samples for the muted, moonlit beat. “He stopped and said, ‘Does that sound cool?’ And we were all like, ‘Oh, my God!'”

100 Greatest Hip-Hop Songs of All Time

The Notorious B.I.G., “Hypnotize”

Notorious B.I.G’s first Hot 100 chart-topper, which hit Number One just weeks after his March 1997 murder, is his supreme pop-rap moment: a litany of boasts and threats, delivered with cool sangfroid over Puff Daddy’s Herb Alpert-sampling candy-corn beat. It was a fitting epitaph, a testament to Biggie’s inimitable flow, matchless wordplay and knack for leavening gangsta sex and violence with punch lines even a toddler could cuddle up to. “Such a likable guy,” said Jay Z. “He’s forever loved by hip-hop.”