Questlove Picks Rap Favorites: Top 50 Hip-Hop Songs of All Time - Rolling Stone
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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.

doug e fresh and the get fresh crew

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

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

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.

run dmc

Run-DMC, “My Adidas”/”Peter Piper” (1986)

With a one-two punch, Darryl, Joe and Jason fulfilled their self-proclamation of becoming kings. But a different type of leader – the people's choice. Run and D were of the people, people who spoke, thought, related and (most importantly) dressed like they did. Russell Simmons always stressed that his younger brother's group should be stripped down to its barest elements so that the people could relate to it. As a result, their strongest presentations contained as little music as possible. All drums, vocals and turntable, and in case they wanted to change the face of history, they'd add a guitar line or two. But they wouldn't make the mistake that their Sugarhill brethren made before them: blending in with the rock elite for acceptance. Clearly, the "meet us halfway at the 50-yard line" plea was not acceptable. Run-DMC insisted that you had to accept them on their own terms.

Proof of this demand working? Run tells the entire Madison Square Garden to hold one sneaker in the air, knowing a magic moment (and millions) were around the corner. Russell Simmons made certain that the heads of Adidas were in attendance to see over 30,000 people holding up their shell-toes. The eventual endorsement was without question. This was hip-hop's tipping point. No longer just music to annoy your grandparents, hip-hop meant big, big dollars. The gates were open: shows in stadiums, albums going multi-platinum, endorsement deals, awards and accolades. This 12-inch single was the Paul Revere announcement that hip-hop was going absolutely nowhere.

grandmaster flash and the furious five

Grandmaster Flash & the Furious Five, “The Message” (1982)

Okay, there is positively nothing I can say about "The Message" that hasn't been said. The world (me included) absolutely froze in its tracks the week it debuted on radio in June of '82. Hip-hop was once known as party fodder, a fad. "The Message" pulled a 180 and proved it could be a tool of sociopolitical change. Being 11, I was as sheltered as sheltered could get. My cousin had to translate all the street terms and jail talk I had never heard before. (I saw nothing wrong with being a "pip" – they danced real good for Gladys! I just had trouble figuring out why a young girl would need one to make it in the streets.) Even my father had to confess he liked it better than that "hippidy hoppidy" song. And when the last minute of the song came on, my dad saw fit that we should have "the talk." Ah yes, "the talk." The one he's been giving me every year of my life. The rules of safety and survival – not with the streets, but with cops. You just gotta understand that the average black man walks around assuming that most people think he's guilty. So the need to make people feel at ease has been instilled in us at an early age. "If a cop addresses you on the street, you are to address him in clear English with 'Yes, sir.' Any movement made must be sllllloooooooowwww. This is to ensure you do not get shot 'by accident.' Do not run in the neighborhood, because that's suspicious…"

I'm sorry, y'all. As I'm typing this, I'm shaking my head – because on one hand, it's so degrading to see these words and it's so emasculating to abide by them. Then I think about the night a few years ago when I got frisked on the hood of the car and then placed in a cop car while they searched for whatever it was they were looking for, and I kept praying they wouldn't figure out how to open the trunk, because there was no way in hell they'd believe I was the owner of a deluxe Scrabble game and a bunch of psychology books from Borders. They told me there was high theft of mini-coops from the dealership I just happened to be parked at, unaware. I told them the irony was, I had pulled over to take a phone call since it was against the law to talk and drive. Of course, driving that type of car in Orange County left me wide open. It was Super Tuesday in 2008, and I was campaigning before the Grammys. I just kept thinking, "Wow, I broke Dad's promise not to ever be a part of this cliche of a scene just like the last minute of 'The Message.'"

I answered questions as best I could, which was working against me because my natural proper English could be seen as "uppity." Add four cops to the mix who are asking questions like "Assistant?" "Your office?" They must have thought we were all quick-thinking Axel Foleys who can double-talk their way out of being arrested. Eventually I was let go when the rental service verified me as the renter. I drove back to my Beverly Hills hotel livid and angry and helpless and about to lose my head. It is like a jungle, still.

de la soul

De La Soul feat. A Tribe Called Quest, Jungle Brothers, Queen Latifah and Monie Love, “Buddy” (1989)

"Sup?" I knew that "Sup." I'd been dealing with that "Sup" since 1983. Chancy and Charles, the bully twins from Addison Street, rolled with their cousin Reggie and terrorized all of us. If you had all your Pacmen and was on a roll on the 10th keyboard, you gave your game up if they wanted it. I spent most of my childhood in the house listening to records, because to go outside was to risk neighborhood bullies. Once we became teens, it wasn't being bullied – it was being shot at that worried me.

I was walking home from school and they were on the corner at Pine Street. It was too late to make a detour or act like I left something important at the library. They saw me coming – Chancy, Charles, Reg, Kev, Smook and Marcus. I made myself scarce from year to year, so there was no real pattern or familiarity with me as far as they were concerned. I just wanted to breeze by unscathed, so that I didn't establish a rep that I could be easily got. Or shot. Of course, dressing how I dressed made me an easy target of getting got. Every step I took got more intense: "Walk like you mean it . . . you're six feet tall . . . you don't take no mess," I tried to convince myself.

Then we were face to face: me and them. "Sup?" I quipped back, heart beating more intense like Bonzo was playing a drum solo in my pulse. Charles started: "Yo!! You look like one of them . . . um, um . . . um . . . one of them, um, um, De La Soul niggas!!!!"

I dunno how I was supposed to respond to that. Do I say "Thanks?" Do I ignore so he can throw his 40-ounce bottle at me? I had a heartbeat of a second, and without thinking, I said, "Oh, that's my favorite group." Then he just yelled with approval: "Ahhhhhhhhhhh!!! That's my shit, that 'Buddy' shit!!! Yeah!!!!"

I can't quite call the time and date, but De La actually made it safe to be me in my neighborhood. So safe, I did more walking around my way in 1989 than I ever did in the 18 years that came before. Like that scene in The Wiz when Evilene dies and her minions' skin peels and they start singing, "Can you feel a brand new day?" I mean, don't get me wrong, it was still the crack era. But at five I was teased for my afro, and at 12 I was teased for rocking pleated Morris Day baggies from the thrift store. I was teased at 15 for cutting holes in my knees like my white friends did at school. Now that De La was in effect, loud colors and loud prints were the norm – and I actually got props! I couldn't believe it. I mean, De La themselves later told me they were in weekly fights knocking mofos out who wanted to test them. And they were De La! I can't call what happened. I once was lost, but now I'm found. Was dweeb, but now I'm . . . .cool?


N.W.A., “Fuck Tha Police” (1989)

My partner Black Thought and I were complete opposites. Me a sheltered band geek, him a streetwise kid from South Philly. But I knew what I liked, and no one was gonna convince me otherwise. I got familiar with N.W.A. because I started religiously reading Billboard magazine in August 1987. I wanted to track the progress of Michael Jackson's Bad album, keeping tabs on it for the three-year duration that it maintained a position. Actually, I think I kept up with Billboard till my band got a deal in '93. Of course, Mike wasn't the only thing I was tracking – I looked at the pop charts, the dance charts, the world charts, everything. The one thing that stood out like a sore thumb were the amateurish looking Ruthless ads for Eazy-E and N.W.A. Having gotten burnt by falling for the west coast while something progressive was going on in the east in the past, I was not gonna be fooled again! (See entry Number Nine on this list, where I'll explain the time I spent a whole summer in Cali jonesin' on Toddy T, while the rest of the States had "The Show" and "La Di Da Di.") Besides, Jheri curls on anyone but Michael Jackson in '87 were not the move. Eric B. and Rakim, BDP, Kane, PE, Jungle Brothers – now there was some innovative hip-hop for your ass. I could take one look and I knew N.W.A. was some sucka-ass motherfuckas. And then . . . lunch time came. 'Riq came running out of breath: "YO!!!!!!!!!! You get Straight Outta Compton yet?" I laughed, like, "Yeah, right." "No, seriously, you hear it?!?!?!!?" Man, I was, like, "Whatever." He snuck me the headphones – oh my God. How could I be so wrong?!?!?! Tariq just looked at me, like, "I know, right?!!?!"

I mean, just by the look of 'em, I thought they'd be stuck in 1985 sounding like Mantronix rejects. What I got was a well produced, well polished, just as exciting as the Bomb Squad kinda production. Beats were changing every second. They were using all of my favorite breakbeats from the Ultimate Beats and Breaks series that was the holy bible of records for any producer in the late Eighties. And I'd never heard no song like this ever. "Is this even allowed?!?!?!?!?!?" I mean, some of the groups I've named previously made me yell "Oh shit!!" on the daily, but rarely did they ever cross the line. (Yes, even Public Enemy's sophomore classic made sense to me.) This was crossing the line. Public Enemy was political, but in a spiritual leader way, like Jackson or Sharpton or Shabazz. N.W.A. was political like the Panthers or the MOVE organization – which almost makes them more political. When the FBI came calling, then that was jackpot. I dunno if a song will ever make me gasp in shock the way that I did the day I heard "Fuck Tha Police" in my headphones. Lord knows. The only time I cut class (besides senior cut day) was the following sixth period, when I skipped orchestra to listen to the rest of the album. Man, I was wrong about N.W.A. I never again judged an album before listening to the evidence before the jury. Word to the motherfucka.

public enemy

Public Enemy, “Rebel Without a Pause” (1987)

When I was 16, I changed high school and churches. Of the two, the church seemed more of a clique-y mean-girl atmosphere than high school. Most of the kids there grew up together, so there was a bond. I was a weird looking kid that they probably thought was more trenchcoat mafia-ish than a "regular" guy. I didn't have much social skills, because I pretty much went to school and came straight home. The youth group of my church organized a beach trip and I decided to tag along even though I felt isolated. Some of the kids I was cool with, but the popular ones really didn't let me play in any reindeer games. I sought refuge in music. The night before, I stayed up and decided to record some songs off the radio, so that if they decided to shut me outta conversations or games, I could at least drown in my headphones.

What I wasn't ready for was the song that saved my life, and theirs. I'm not trying to make this weird. But I do feel like every teen goes through an angsty "woe is me"/"fuck the world" period. Maybe it's loneliness, maybe it's pressure, maybe it's innocence lost. For the most part, I've often found that music can be a great remedy for that unchanneled anger. Black music was the one genre that I had never found an effective means of release – I mean, that's what speed metal was for, and moshing, and punk culture. And who knows what the consequences are for those that don't have this release?

On the radio, Lady B warned us all to record her next set and thank her later. She was dead serious. She was going to play us something, and she didn't know what to make of it. Silence. Then she said, "Start your tapes…"

"Brothers & sisters!" The voice of Jesse Jackson came booming over the speakers. "Brothers and sisters! I don't know what this world is coming to!!!!!!" Two horn stabs, a scratch, and –

Oh my God. What the hell is this?!?!? It was the sound of your brain in a vice grip. The sound of a tea kettle screaming for its life? The scream of a bunch of teens feeling my wrath!?? The steam of uncried tears??! It was like each squeal of St. Clair Pinckney's alto sax represented my anger at something – but what? I wanted to blast this song to smithereens, but it was 1:30 a.m. and my parents were asleep. That did not stop me. I played and played and played and played and played this song, over and over and over, until it was 6 a.m. and I'd been listening to "Rebel Without a Pause" for four and a half hours.

I took a cat nap, but woke up at 7:45 because I could not get that squeal out of my head. I made a 60-minute cassette with that song and only that song. I copped 16 batteries, 'cause you never know when you will need your Walkman to work for 4,000 hours in a row. I got in that church van at 10:30 a.m., and sure enough, only two of the 14 kids acknowledged me. I didn't care. I blasted that song until my Sony sports headphones cried for mercy. The whole two-hour trek, I annoyed the shit out of them – for the squeal could pierce any soundscape. It was like I needed that song to just calm me down and keep me sane. I needed to channel the rage I was feeling. Actually, all of America needed a channel for its rage. PE offered that opportunity with each panic-packed second. Now I'm way more calm than I've ever been. But at that one time in life when I didn't have a friend or a care in the world, this song was my refuge. Believe the hype.

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