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The 50 Greatest Hip-Hop Songs of All Time

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Looking for the full list of the 100 greatest hip-hop songs of all time? Check it out right here.

Editor’s note: To make this list, Rolling Stone asked 33 artists and experts – from Rick Rubin to Busta Rhymes – to choose their favorite hip-hop tracks, then crunched the numbers. Click to read the full list of voters.

What Makes a Great Hip-Hop Song?
An Introduction by Ahmir “Questlove” Thompson

I was eight years old when “Rapper’s Delight” made its world premiere on Philadelphia radio. It happened at 8:24 p.m. on a Thursday, after a dinner of porgies, string beans and creamed corn. Me and my sister, Donn, were sneaking a listen of the local soul station while washing dishes­ when an army of percussion and a syncopated Latin piano line came out of my grandma’s JVC clock radio – what appeared to be Chic’s “Good Times.” How was I to know that my world would come crashing down in a matter of 5, 4, 3, 2 . . .

I said a hip, hop, the hippy to the hippy/To the hip hip hop, you don’t stop. . . .

The next night, I was prepared, with a prehistoric tape recorder in hand and a black-and-white composition notebook. My boy Aantar became my agent that week, scheduling performances of the song in exchange for snacks or hand-holding with girls in gym class. “Rapper’s Delight” turned this future high school band geek into a superstar for the month of October 1979.

Some of the most powerful hip-hop songs are tracks with elements so simple your brain would explode trying to explain their logic: Take the unstoppable two-note guitar stab in Craig Mack’s “Flava in Ya Ear.” (I hounded the producer, Easy Mo Bee, for 17 years for the secret behind it – then wanted to throw someone out the window when I heard how basic it was.) Or the huge sound of the Roland 909 on Schoolly D’s “PSK” – an echo that seemed like it came from a church cathedral eight city blocks wide.

These sounds had incredible power if you grew up with hip-hop: There was the summer I spent trying to match the mix to “The Adventures of Grandmaster Flash on the Wheels of Steel,” note for note, on two Fisher-Price turntables. (My father, unimpressed, told me, “There ain’t a living spinning other people’s music” – little did you know, Dad, little did you know.) There were so many times when a song premiere could stop you in your tracks, then become a subject of discussion for the next four hours: in the high school lunchroom when me and Black Thought heard “Wrath of Kane” for the first time, or my first listen to “Fight the Power” – it sounded like Pharoah Sanders and Rahsaan Roland Kirk had gotten into a knife fight.

Hip-hop gives listeners sets of rules that you follow like the law, only to see them change every five years. I’ve seen my reactions to hip-hop change from age nine (“What the hell was that?”) to age 14 (“That was incredible!”) to age 22 (“Wait . . . are they allowed to do that?”) to age 29 (“It was kinda different when I was a kid”) to now (“What the fuck was that?!“). I’ve seen Vanilla Ice’s “Ice Ice Baby” go from ruling the world to being a musical pariah to being an ironic statement in my DJ set that makes people smile.

The greatest hip-hop songs have the power to pull energy and excitement and anger and questions and self-doubt and raw emotion out of you. It could be a song that sets your neighborhood on fire (“Rebel Without a Pause”) or a song on your headphones that makes you rethink what hip-hop is (Ultramagnetic MCs’ “Ego Trippin’ ”). The common thread is change. The best hip-hop songs aren’t blueprints – they are calls to action, reminders that you can start a revolution in three minutes. Just keep that clock radio on.

25

Big Daddy Kane, ‘Ain’t No Half Steppin”

Long Live the Kane, 1988

When Jay-Z christened Brooklyn’s new Barclays Center arena earlier this year with a series of eight straight shows, he brought out only one guest rapper to share his stage: Bed-Stuy native Big Daddy Kane. And for good reason. Antonio Hardy was the master wordsmith of rap’s late-golden age and a huge influence on a generation of MCs. On “Ain’t No Half Steppin’,” his tone is rich and commanding as he rocks tightly coiled extended metaphors over Marley Marl’s laid-back groove (based around the Emotions’ fine 1972 cut “Blind Alley”): “Rappers, you better be/Ready to die because you’re petty/You’re just a butter knife, I’m a machete.” Legend has it that even the Eighties’ greatest rapper, Rakim, turned down a challenge to go mic-to-mic with Kane.

24

Rob Base and DJ E-Z Rock, ‘It Takes Two’

It Takes Two, 1988

“All I know is, it’s a club banger,” Rob Base said of his biggest rec­ord. Actually, it’s the mother of all club bangers, a pop-rap opus that’s as absurdly fun today as it was 25 years ago. Mixing hip-hop and house music, lifting liberally from James Brown background singer Lyn Collins’ 1971 song “Think About It,” Rob Base and DJ E-Z Rock’s 1988 smash was also an ode to understanding and respect, one that brought everyone together under a groove – from block parties in Harlem to slumber parties in Des Moines. The song was produced by Teddy Riley, who deployed a similar jump-up syncopation as the king of New Jack Swing. Base later said, “I wanted people to get up and dance and not have to worry about fightin’ and arguin’.”

23

Eric B. and Rakim, ‘I Know You Got Soul’

Paid in Full, 1987

“When I’m writing, I’m trapped between the lines/I escape when I finish the rhyme,” explains Rakim, rocking the kind of jam that would soon disappear once copyright lawyers stepped up their game. Eric B. looped a chunk of the James Brown-produced song of the same name by Bobby Byrd and the J.B.’s All Stars. But all turnabout is fair play: The British mix masters M|A|R|R|S constructed their hit “Pump Up the Volume” around a sample of Rakim saying that memorable phrase on “I Know You Got Soul.”

22

EPMD, ‘Strictly Business’

Strictly Business, 1988

The greatest thing about EPMD’s inaugural single is the duo’s self-produced beat – a cornucopia of blatant samples from the golden age of artistic pilfering, with Eric Clapton’s “I Shot the Sheriff” busting wild-style moves on the floor next to Mountain and Kool and the Gang. Erick Sermon and Parrish Smith’s laid-back rhymes were revolutionary in their way too. Most rappers in 1988 were still stuck on loud, clear cadences. EPMD’s casual, goofy approach to the mic laid the groundwork for generations of chilled-out – as well as weeded-out – rappers.