Questlove's Top 50 Hip-Hop Songs of All Time

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I was eight years old when "Rapper's Delight" made its world premiere on Philadelphia radio. It happened on 8:24 p.m. on a Thursday night, 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 we washed 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," or a good duplicate of it. How was I to know that my world would come crashing down in a matter of 5, 4, 3, 2, 1 . . . 

I said a hip, hop, the hippy to the hippy/To the hip hip-hop you don't stop/The rock it to the bang bang a boogie say up jump the boogie/To the rhythm of the boogie the beat!

Philadelphia row house walls were thin, so I could hear the neighbors on both sides blasting this jam on their stereo. My friends starting calling, way past grandma's weeknight deadline: "Did you just hear that!?" It was like our version of Orson Welles' War of the Worlds. The next night, I was prepared, with a prehistoric tape recorder in hand and a black-and-white composition notebook. This song single-handedly made me the man in my fourth grade lunchroom. My boy Aantar became my agent that week, scheduling performances and negotiating written lyrics 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.

There was nothing like growing up with the power of hip-hop. There was the summer I spent trying to match the mix to "Grandmaster Flash on the Wheels of Steel" note for note on two Fisher Price turntables. (My father, unimpressed, told me that "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: The high school lunchroom when me and Black Thought heard "The 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.

Not every big song was a "Eureka!" moment of elation. When you are a hip-hop devotee of my age, you've been given a set 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 but [shrug] I guess I can't fight it") to now ("What the fuck was THAT?"). I've seen "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.

So what makes a great hip-hop song? It's when a track has the power to pull energy and excitement and anger and questions and self-doubt and raw emotion out of you. Whether you're loving every second of it ("The 900 Number" by DJ Mark The 45 King) or not (Vanilla Ice). It could be a song that sets your neighborhood on fire ("Rapper's Delight") or a song on your headphones that makes you rethink what hip-hop is (Schooly D's "PSK"). The common thread is change. The best hip-hop songs aren't blueprints – they are calls to action, reminders that you change the world in three minutes. Just keep that clock radio on.  

–Questlove

ADDITIONAL NOTE: For this top 50 list, I decided to concentrate on 1979-1995, the former being the year I got my first taste of hip-hop, the latter being the year my major-label debut with the Roots made its mark. I wanted to concentrate on the period that I was not professionally involved in the art form. I wanted to celebrate the period that built and led to the influence that got me a record deal.

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