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

What makes a great hip-hop song? Ahmir “Questlove” Thompson chooses his favorites.

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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.  

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.

beastie boys

Ebet Roberts/Redferns

7

Beastie Boys, “Hold It Now, Hit It” (1986)

Ronald Isley once told me a story about how he and his singing brothers had to show friends and family their This Old Heart of Mine album with their heads down, because label head Berry Gordy thought it was a wiser marketing move to sell the album with a teen white couple in embrace on a beach as opposed to three, uh, Isley brothers. Twenty years later, Russell Simmons used a similar tactic. Most of us assumed the Beasties were Puerto Rican, 'cause there was no way humanly possible that three white boys had that much flavor. It wasn't even a "if they were white we'd never have given them a chance" thing. Our minds were so closed and tunnel-visioned that we just knew that hip-hop was a culture that only blacks and latinos appreciated, mostly because we were not rhythmically challenged. Boy, were we in for a rude awakening.

Def Jam used a two-year buzz period to fine effect. For those outside of the New York perimeter, their first real strike on hip-hop radio – Lady B's street beat in Philly – was "Beastie Groove," with its hard-ass drums, double time rhymes, the whiniest and gruffiest voices in hip-hop and a cool slang term that all of Philly has yet to figure out: "Yo, just 'fessin man, I don't even wanna hear it, you just 'fessin." Their second assault was MCA's solo joint "Drum Machine," which pretty much took up where "Beastie Groove" left us. There was one slight misstep, "She's On It" from the Krush Groove soundtrack – but the Beasties' cameo in the film was so minuscule that their lil' white secret wasn't totally given away just yet. And no real hip-hoppers saw Madonna's Virgin Tour all that much.

So the Beasties' first real footsteps in our hearts and radar came courtesy of this song. Its high position is based on the accidental way that they arrived. The initial test pressings of their "Hold It" 12 inch placed the (historic first) "Acapulco" version on the A side and its full album version on the B side. DJs instantly played the vocal-only version, which was magically effective. The chorus and bridge were still intact: Kurtis Blow's "hold it now" from "Christmas Rapping" and Kool & the Gang's "Funky Stuff" horn intro coming at you like a locomotive downhill. I can't explain how exciting that part sounded. It sounded even bigger and grander coming from an a cappella tradeoff of three jazzy-sounding instruments called Ad Rock (soprano), Mike D (tenor) and MCA (baritone). This was the "rhyming for the sake of riddlin'" that Chuck D lambasted in "Don't Believe the Hype." This was hip-hop's first non sequitur – all pop culture reference, random tradeoff. Most crews would go verse for verse or line for line, even. The Beasts were going syllable for syllable with the ease of the Harlem Globetrotter magic circle. I mean, come on. You gotta love a cat who takes six seconds to say "chef boyar-deeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee."

So imagine my dismay when I finally got the album version on Licensed to Ill and heard all this intrusive drum machine. Man, I was so disappointed. They didn't trust us enough to just see the magic of the wordplay and the chemistry between the three. I would often make custom Ill records and reinstate the drumless version of the song in its place where it belongs. 'Cause Lord knows, I hated that drum machine. Actually, 20 years later, in a freak occurrence, being the historical artifact nut I am, I purchased that very drum machine Rick Rubin used for four years – because I secretly loved it.