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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.

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Rob Base and DJ E-Z Rock, “It Takes Two” (1988)

For all of the James Brown/Clyde Stubblefield "Funky Drummer" sample folklore talk out there, I rarely hear conversation about the James Brown drummer who actually got sampled more than my idol Clyde did. John "Jabo" Starks was the Beatles to Clyde's Stones. A clean shuffle drummer to Clyde's free-jazz left hand. Clyde fit more with Public Enemy's pop-art-rock sporadic vision. Emphasis on everything surrounding the one beat, thus making other parts of your body shake in order to keep up with his rhythm – see "Mother Popcorn," "It's A New Day" and "Give It Up or Turn It Loose." Jabo's sparse, all-on-the-one funk was more at home with conservative soul lovers – see "Hot Pants," "Escapism" and "The Payback" – which is why it makes total sense that Clyde's panic style was the anchor to drum and bass music and other experimental styles, while Jabo was the anchor of the New Jack Swing movement. He was always reliably on the one and never, ever in the way. Jabo's go-to magnum opus was on the five-break-filled JB-produced "Think (About It)" by Lyn Collins. James' holy ghost yelp almost threatens to upstage Starks' show, but it's Starks' steady glide that gave R&B music its blueprint some 15 years after its release.

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Afrika Bambaataa and the Soul Sonic Force, “Planet Rock” (1982)


I wasn't allowed to play urban stations on my clock radio when I went to sleep as a kid, but that didn't stop me much. Between 1977 and 1980, Soul Train came on at 1 a.m., right after Saturday Night Live went off. Why my parents were so strict with some things and lenient with others was beyond me, but I was allowed to set my alarm to 12:45 a.m. every Saturday, just as SNL's music guest was doing their second song, so I could watch my favorite show afterwards. Then it was back into bed at 2 a.m. so I could wake up for Sunday school the next morn.

For urban radio on late Saturday, there wasn't an idea of live remotes from such and such club as they do now. Normally you'd get the usual disco fare from 8 p.m. till 2 a.m., then after that the 2 a.m. to 6:00 jock would play some real left-of-center progressive stuff, like a Mandrill album cut or maybe Bill Withers' 10-minute long "City Of The Angels." I know it's hard to believe, but there was a time in life in which radio was the progressive epicenter of what was hip and next. I mean, it built and contracted my geek behind, right? Right?

From '69 to '89, black music was on a roll with what was hip. German prog outfit Kraftwerk's "Trans-Europe Express" was usually on around this time late Saturdays. And man, it was hypnotic. I never knew what to call it, and there was nothing like a Shazam app to tell me song titles, so I'd have to suffer for a week until the next Saturday with a tape recorder ready to go the second I heard all that futuristic electronic shuffle drumming and robotic synths. When 1979 came, I never heard Kraftwerk again on radio. But that song always stuck in my head like a minuscule movie popcorn kernel I could not get rid of. All that changed when I was at a roller-skating party for my neighborhood friend Shawn Riley. His old brother was the DJ. I never heard an 808 drum machine before – it was quite overwhelming to take this all in and be an 11-year-old. And finally to hear that Kraftwerk song after all these years, it was a mystery solved. I ran to the booth and begged to know what it was. They handed me the 12-inch and asked, "You like this? It's too fast!" Then they gave it to me. That moment was my Mean Joe Green with the kid in the Coke commercial. I still have, DJ and cherish that "Planet Rock" 12-inch record to this day.

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Run-DMC, “Rock Box” (1984)

Without "Rock Box," the historic "Walk This Way" would never have happened. Its importance wasn't even the way it fused rock with hip-hop in a convincing manner. Manager Russell Simmons always felt that the glitz and showbiz of post-Parliament/Funkadelic black music had diluted hip-hop's magic. All that came before Run-DMC looked like it was part of a Broadway production. Superheroes were everywhere, and for the first time in history, black heroes were on semi-status as the status quo. (Well, don't tell the ghost of Rick James this white lie.) The point was, hero worship was at an all-time high. Run's older brother was onto something decades before the reality TV generation came into its own: America wanted stars that looked and dressed like they did. That's always been the pendulum of the music biz. Half the decade you worship a godlike figure (Elvis, mop-top Beatles, Seventies Bowie, late-Eighties Madonna, Motley Crue) and the other half you get into people that look just like you do (non-mop-top Beatles, Eighties Bowie, Early Madonna, Nirvana). Even though they were the gatekeepers for the second stage of hip-hop (1982-1987), Run-DMC officially ushered in the B-boy period of hip-hop, where the everyman had a chance to escape poverty and invisibility and make it. Including this band geek of a scribe. Now the cherry on top was finding the perfect middle in which they could hit two birds with one stone – rock fans and hip-hop progressives. Of course, MTV was wide open, having let MJ and Prince in the door some two years before. So this was the perfect formula, the single that knocked down many obstacles enabling hip-hop to become the new gospel.

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Dr. Dre feat. Snoop Doggy Dogg, “Nuthin’ But a ‘G’ Thang” (1993)

I once heard someone say that the paydirt magic of "'G' Thang" was that hip-hop finally found an anthem that made white people want to deny their whiteness. (Note that I didn't say "want to be black" – that's been going on since the beginning of American music.) I gotta admit, before "'G' Thang," the biggest victory hip-hop could claim was getting its share of play in the club and on the air. This was a whole 'nother monster. The attraction really wasn't the song – and I'm biased a little, 'cause the good doctor sampled my parents' Seventies project Congress Alley for the hook. (Google "Are You Lookin'.") The attraction was the lifestyle. 1992 was a turning point of irony for Clinton's America. The seeds of leadership lay in the hands of two people. One, Kurt Cobain – he represented turning his back on the privileged glamour birthright awarded to all rockers, an anti-hero that meant it. And two, Dr Dre. He didn't necessarily revel in the glamorous lifestyle once denied to him, but he wrote the blueprint and Cliff Notes (I'm old school, sue me) that Sean "Puffy" Combs would utilize and rule with an iron fist down to the last Ciroc drop. Money was made, dreams were fulfilled, lives were lost, lines were crossed. This single would completely turn hip-hop on its head. The chronic proved greener on the other side – but at what price?

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Eric B. and Rakim, “Eric B is President”/”Check Out My Melody” (1986)

If I were given hip-hop's timeline wand and asked to draw the line in the sand that would define the moment that hip-hop stepped into the post-modern age, this song would have to be my choice. Rakim's no-nonsense, straight-laced, non-minstrel, dead-panned delivery is one of the hardest sells in hip-hop. I mean, think about it. Some of our favorite characters in hip-hop are just that: characters. Colorful, all over the place, full of inflection and humor. Rakim was none of that. Pssssh, even his most humorous punchline –  gotta remember, "President" was a part-time response record to Janet Jackson's unexpected red-hot "What have you done for me lately" – was dry enough to make Steven Wright take notice. "You scream I'm lazy?/You must be crazy/Thought I was a donut, you tried to glaze me . . . "

Rakim was John Coltrane personified as MC: all cool and steady hand. Run-DMC and  the Beastie Boys were screaming hip-hop's power from the top of the mountains. Rakim was doing the exact opposite – mountains came to him. Just to prove this was no fluke, his every word on the B-side "My Melody" was like the holy scriptures. Damn near the 10 Commandments for any real MC worth his or her weight in gold. There was no MC from this new Renaissance period that wasn't running for cover when Rakim was within earshot. Remember those old Westerns, when the cowboy dressed in all black comes to the saloon and the tavern gets all silent and even the piano player stops the music? I don't, either, but you get the picture I'm trying to make. Rakim turned MCing into a serious art. He was no joke.

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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.

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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.

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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.

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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.

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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 wa