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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.

grandmaster flash and steel wheels

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10

Grandmaster Flash and the Furious Five, “The Adventures of Grandmaster Flash on the Wheels of Steel” (1981)

I've only had one pugilistic episode with my older cousin David, back when we were kids. If there was a surefire way you wanted to get my goat? All you had to do was prove that you thought you were a better music expert than I was. Actually, what irked me more was when non-musical experts insisted their word was law. David asked me if I ever heard the song "Fab 5 Freddy" – so he proceeds to recite the lyrics, "Fab 5 Freddy told me everybody's fly/DJs spinnin', I said, 'My my'/Flash is fast, Flash is fast, Flash is fast, Flash is cool . . ." What self-respecting Blondie fan would mangle the lyrics to "Rapture" like that? I corrected him the best, most condescending way any 10-year-old critic could: "She doesn't repeat 'Flash is fast' like that, she says it once." David protested that she did say it three times, and what does Dagwood's wife have to do with this song, I'm talking about Grandmaster Flash . . .

I'll spare you guys the Abbot & Costello "Who's on first?!" routine and cut to 40 minutes later, when we are sneaking on my dad's (do not ever touch my) turntable so David could show me exactly how "Flash was fast." Lemme just put it this way: summer of '81, longest punishment ever. In hindsight, though, I was willing to suffer for Grand Wizzard Theodore's sins. When finally allowed out the house seven days later, I officially got to hear what David was talking about. "The Adventures of Grandmaster Flash on the Wheels of Steel" represents the first example of cuttin' and scratching. A five-minute history of what a night in the Bronx musta been like. Remember – live bands were called in to recreate the breaks once hip-hop went in the studio in '79. Technology wasn't up to par for turntables to be used in the studio back then. Because I owned every last record that Flash used – I'm still kinda curious what made my parents buy Incredible Bongo Band's "Apache" in a non-hip-hop-DJ context – i spent that entire summer trying to match that mix note for note on two Fisher Price turntables I'd had since childhood. My dad would often offer his two cents, shaking his head in disappointment with that jigga-jigga-jigga noise he was hearing. He added in that I needed to "spend more time on them drums instead of destroying all them good records," 'cause "ain't no future in these records people done already made." I should be making music instead, 'cause "there ain't a living spinning other people's music." Oh, little did you know, Dad. Little did you know.

doug e fresh and the get fresh crew

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9

Doug E. Fresh and the Get Fresh Crew, “The Show”/”La Di Da Di” (1985)

Classic regionalism tale: I spent the entire summer of '85 with relatives in Los Angeles, California. This was the halfway mark of the first decade of equal opportunity for the superpowers in music – specifically, for black artists to get their fair share of the pie. Michael, Prince and Lionel sustained the decade's first half, and it seemed like the sound of hip-hop was going to claim the second half. My cousins always had this AM station on constant play called KDAY. Before that, I could never imagine a time when I could hear hip-hop for 24 hours on a station. Normally you got it on the weekends for three to four hours, recording every second so you could sustain yourself for the week. But out in L.A., it was a whole new ballgame. And the anthem for that summer? Toddy T's "The Batteram" –a song about when a knock on your door from the po-po just ain't enough. It made sense: Gang violence was at an all-time high, so of course the music was going to reflect how they were living. I mean, you heard "The Batteram" from every ghetto blaster and car no matter where you went. So imagine my surprise to return back to my beloved Philadelphia and brag to my friends about how incredible my summer was, only for them to be like, "Batter what?" I didn't have a cassette of the song to prove to them that they'd better get with it or get left in the cold. Oh boy, little did I know. No one in Philly could help: local DJs, college hip-hop radio formats, roller skating rink cats – nobody had heard of this song!

My neighborhood pal Greg told me, "Nobody knows 'Batterram' because everybody is all caught up in 'La Di Da Di.'" He told me "La Di Da Di" was so popular I could actually hear it on a weeknight on mainstream radio. So instantly I thought this was a lie. He assured me it wasn't and told me to make sure I had a tape ready to record at around 9:50, when the Power Nine at 9 came on. Sure enough, I sat there, jaw dropped, as the most distinctive voice I ever heard rap held the Number One and Two slots from what I was told was the entire summer. I felt foolish going on about Toddy T when clearly the future was now, and I was not at the forefront of its discovery.

I mean, point blank: Slick Rick's voice was the most beautiful thing to happen to hip-hop culture. He is our Bill Cosby, a master storyteller and deliverer. Don't get me wrong, Doug is no slouch neither. (And show of hands: How many of y'all knew that New Jack Swing pioneer Teddy Riley co-produced "The Show"?) But this was one of those "a star is born" moments in hip-hop. Every last line of "Da Di" has been the anchor of many a hip-hop classic, and it's no wonder. Rick is full of punchlines, wit, melody, cool cadence, confidence and style. He is the blueprint. No one bragged like him, no one name-dropped like him, no one sang like him, no one was funny like him. Nobody. And as this song inches to its thirtieth anniversary, it's clear that no one will ever, ever sound like him.

public enemy

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8

Public Enemy, “Fight the Power” (1989)

Black America saw itself take a giant leap forward in the Civil Rights period, just to slip 10 miles backwards in Reagan's America. The first sign of disillusion in the sound of black music came courtesy of Sly and the Family Stone's muddy 1971 album There's a Riot Goin' On. Twenty years later, the crack epidemic came and singlehandedly almost wiped us out. Those who used, those who pushed, those who lived with those who used and pushed, and especially those who made it a life mission to avoid those who used and pushed. The elderly and young were prisoners in their homes – thank God for Dad's record collection or I'd have gone crazy. It just wasn't safe.

Public Enemy managed to explain the madness of the crack era in its sound. (I'd say every period of hip-hop was associated with its drug of choice: '77-'82 was post-disco coke, '82-'87 was the 40-ounce/B-boy period, '87-'92 was the panic/crack era, '92-'97 was the weeded and blunted era, '97-'02 was the sexy/ecstasy period, '02-'07 the sizzurp era, and so on.) PE ruled the '87-'92 crack period because its musical backdrop matched the times: Songs were now 115-125 bpm instead of the previous 95-110 fare. Melody was thrown out the window – this was Pharoah Sanders and Rahsaan Roland Kirk in a knife fight, this was your four-year-old sneaking a triple espresso when no one was looking at 10 p.m., this was playing Skrillex at your grandma's funeral, an air raid siren in a nursery. This was music's worst nightmare.

Flavor Flav's batshit crazy stance was used as bait (I fell for it) to attract the unaware. Once trapped inside, Chuck D's baptist preacher rapid-fire scream was the nail in the coffin. The best sweet and sour combo in hip-hop. Actually, the original contrary duo in hip-hop. 1989 marked a particular anger in New York: Tawana Brawley's rape case, Yusef Hawkins' murder in Bensonhurst, Michael Griffith's murder in Howard Beach. In one five-minute cyclone of a song, Chuck D pulls his inner Howard Beale out and declares he is mad as hell and he is not going to take it anymore. I mean, my dad and I had world-class debates on the merits of Public Enemy, but even that one-two punch of Elvis and John Wayne almost made my dad say "Yeah!" Of course, right before i could yell that he was a PE fan, he quipped in the next breath, "But that's still not music." I know, Dad. Trust me. I know.

beastie boys

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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.