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

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A Tribe Called Quest, “Bonita Applebum” (1990)

My former Universal Records product manager, Grace Harry, hates when I introduce her (actually, I wait until her, well, applebum is turned the other way) in a whispered tone as "the real life Bonita Applebum that Q-Tip wrote about when they were dating in high school." There is no shame in that game, Grace! This is the song that truly birthed the idea of neo-soul. It was the coolest love song hip-hop has ever offered us. And that is miles better than being effective.

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Gang Starr and Nice & Smooth, “DWYCK” (1992)

The most powerful B-side of all time in hip-hop. No sugary hooks. Rhymes and ammo. This was the go-to instrumental for many a cipher in the early Nineties. This single marked the true arrival of Gang Starr.

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DJ Jazzy Jeff and the Fresh Prince, “Summertime” (1991)

The level of wildfire-speed word of mouth this single got in '91 was unbelievable. No one could believe it. I'll describe it the same way Black Thought rang me up on the phone after he first heard it: "It's like he lost all that animated happy flow and did Rakim's 'Paid in Full' flow . . . but better than Rakim!!!" I kinda have to say, this single was the best pop hit Eric B. and Rakim never got to record. For the first time, the Fresh Prince's Clark Kent was given a back seat while Will's Supermanisms took the wheel. This gave you the real view of the streets of Philadelphia.

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Public Enemy, “Shut ‘Em Down (Pete Rock Remix)” (1991)

The passing of the torch in hip-hop is never a happy occasion. It's mostly filled with bitterness and shit talking. Chuck D clearly knew that PE's five-year reign was coming to a close. Once you realize and come to grips with this fact. you can either fight the power, or play diplomat and go out like a champ. If only every act in hip-hop thought like this. Thank God Chuck D chose the latter and let young upstart Pete Rock take over the boards to give PE's "aight" song the decade' second best facelift. (The first goes to Black sheep's "The Choice is Yours.") This song marks the renaissance period of New York hip-hop that was more jazz-centric over the usual Southern soul bed it was used to. A marvelous closing-credits soundtrack to a storied streak of revolutionary madness from the best group in hip-hop.

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A Tribe Called Quest and Leaders of the New School, “Scenario” (1991) / Marley Marl, “The Symphony” (1988)

Posses in effect.

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Trouble Funk, “Pump Me Up” (1981)

Even though – ahem – Philadelphian Grover Washington, Jr.'s "Mister Magic" is go-go's blueprint (prove me wrong, I triple dog dare you), I'mma let D.C. have this one. This entry, as well as the overall genre of go-go music, is easily the most overlooked and under-appreciated song on this entire list. Sure, the godfather of 'em all Chuck Brown's "Bustin' Loose" gets the glory, but stylistically I consider "Bustin'" a funk bomb that defiantly stared the disco genre in the face like a bully in the lunchroom. "Pump Me Up," however, was the first true go-go joint that hip-hoppers adopted and claimed as their own. Taking elements from the salsa world (congas, timbales, shakers, wood blocks, cowbells) and turning them on their heads, it morphed into a tribal ritual so hypnotic that jams could go on for 20 minutess and you'd never know the difference. Before the idea of sneaking in Mom and Dad's record collection to cut and scratch breakbeats, this particular gem gave us our first true contemporary break to practice on. This came months before Spoonie Gee's "Love Rap," by the way – the second great hip-hop breakbeat.

Everyone ate this record up in the summer of '81. Psssh, DJs even made complete 12-inch singles of them just cutting the intro of the song. You can clearly hear the blueprint of Rick Rubin's greatest jams ("Rock The Bells," "She's Crafty," the end of "99 Problems") and Teddy Riley's work ("The Show," "Mr Big Stuff," "Teddy's Jam") in this composition. For the life of me, I could never see why black people's jam band music hasn't crossed the state lines. But if there ever was a genesis for some of hip hop's greatest go-go moments, here it is.


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EPMD, “You Gots to Chill” (1988)

Before De La's "Me Myself and I," EPMD made an art of looping "barbecue jams"  – songs your old uncle rocks at the family function – to fine effect. This is the record, in my opinion, that marked the beginning of the idea of G-Funk. Slow flow, lazy drawl, tough talk, and a Roger Troutman sample that even your uncle could embrace. The makings of a classic.


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Ultramagnetic MCs, “Ego Trippin'” (1986)

I once heard an interview with Run-DMC where they were kinda going off about how they weren't that much into Kool Keith. For the longest, I would scratch my head. Who could resist Keith's futuristic nerd flow? And then it hit me, once I went back to the very beginning: Most will see "Ego Trippin'" as the debut of the essential breakbeat classic "Synthetic Substitution." But the radical feel of the song distracts from the heart of the matter: They were going for Run and Co's neck!

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Pete Rock and C.L. Smooth, “They Reminisce Over You (T.R.O.Y.)” (1992)

Hip-hop's fourth stage – '92-'97, a.k.a. the renaissance period – was a peak into the "boring" section of our parents' record collection. Of course, the obvious stuff (P-Funk/James Brown/Kool & the Gang) were the tools of the third stage – '87-'92's classic period – and used to great effect. If this period served the jocks well in Hip-hop High, then to make high art required a specific flexibility that the nerds excelled in. Soon artists like Monty Alexander, Vic Juris and Ahmad Jamal were allowed to play in the same reindeer games that their funk peers previously denied them access. The leaders of the New York renaissance were Gang Starr's DJ Premier, Tip and Ali from A Tribe Called Quest, the Large Professor of Main Source, Diamond D and Heavy D's cousin from Mount Vernon, Pete Rock. They made smooth jazz rugged by fusing it with crispy breakbeats. So lethal was this combination – especially with Tom Scott's rolling sax etched in your brain like a tattoo – I'm certain to this day that people forget that this was a song of mourning and reflection for a loved one. This song proved that hip-hop was as gorgeous as a painting in the Louvre.


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UTFO, “Roxanne, Roxanne” (1984)

Historians always note this as the seed that spawned a thousand responses. But I never hear historians noting this was the first hip-hop song that sampled a breakbeat: Billy Squier's "The Big Beat."

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The Pharcyde, “Passin’ Me By” (1993)

Quiet as it's kept, the Pharcyde truly never got the recognition they deserved. They were the left of the left coast (think renaissance for the palm tree set), and Dre's Chronic smoke was blocking everyone's view. The accompanying video was high art and probably the best hip-hop clip Spike Jonez never got his hands on. Rare when a song can present a vulnerability so real you don't even notice it. The high school loser who never made it with the ladies finally found his theme song.

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Audio Two, “Top Billin'” (1988)

Mastering the art of "flipping" is an accomplished feeling. Flipping is when you reconstruct an original idea past the point of recognition. The first steps of a producer's journey is taking a breakbeat and chopping it to bits to rebuild a new idea. I don't know what to make of "Top Billin'" – I mean, it's all over the place!! Milk sounds like your kid brother with a brush in hand and your sunglasses on, pretending he's the black Ad Rock from the Beastie Boys in the mirror. The minimalist drum backdrop was both irksome and innovative. Urgent yet simple. Crazy yet bland. All those things . . . but try once to get it out of your head. See!!!?

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Mobb Deep, “Shook Ones Part II” (1995)

"I'm only 19, but my mind is old/But when the things get for real, my warm heart turns cold." Most acts overdo the tough guy schtick and run the risk of turning into caricatures of themselves. This song is the rare example of how choosing a deadpan, understated delivery can incite fear better (Team De Niro) than a bunch of rabble-rousing shit talkin' on a Saturday night (Team Pacino).

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Public Enemy, “Welcome to the Terrordome” (1990)

Leave it to Public Enemy to turn a Temptations song about a utopian society in which one could relax and ease their mind ("Psychedelic Shack") into a paranoid rant that was the equivalent of a madman with a migraine. It was the sound of a drill to the temple. It was the feeling of a having a five-yard lead in front of a downhill bound train this close to destroying you to bits. Chuck D was so very under the gun in 1989. Our beautiful reward? Watch a man lose himself, right on the razor's edge of panic.

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Eric B. and Rakim, “I Know You Got Soul” (1987)

For all of their guard-at-the-gate-ness for the classic period of hip-hop, you were either team James Brown (mostly East Coast) or team P-Funk (mostly West Coast). Rarely did you ever hear the two worlds colliding in hip-hop's musical backdrop. How fitting is it that two side projects from these camps – the drum foundation is Funkadelic, the guitar loop from James' right-hand man, Bobby Byrd – formed a union so threatening it forced Public Enemy's Chuck D to create my number one pick on this list in a knee jerk response to him getting a mid-life crisis moment when he first heard this song. "I Know You Got Soul" solidified Rakim's status as the second coming. Only his third 12-inch single, and already he was declared the king of kings. Hard to imagine a time when the most intelligent MC ruled the kingdom of hip-hop. I wish those days could come back once more.

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Das EFX, “They Want EFX” (1992)

Up until this particular release, hip-hop was a law-abiding, no-violating zone when it came to creative license. Das-EFX made pop culture gibberish sound so fun that everyone was forced to change their style. You know what kind of power that is? To be that infectious that you can make an entire culture follow your lead? The downside, of course, is their style was run into the ground, leaving you no seconds at the dinner table.

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Biz Markie, “Just a Friend” (1990)

The charm of this song will never, ever die. How do you mend a broken heart? Sing about it!