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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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MCA Records


Son of Bazerk feat. No Self Control and the Band, “Change the Style” (1990)

Every connoisseur list has one obscure must-have. This is that must-have. The most brilliant swan song ever created by Public Enemy's Bomb Squad production team. After this record, their patented "everything but the kitchen sink" style of production was deemed financially impossible, and illegal. (So illegal I had to beg Chuck D to give me a copy after I lost my Son of Bazerk album.) One listen and you'll know why this song must be championed. They cram hip-hop, dancehall, oldies, doo woop, Motown soul and Bad Brains (!!!!!) in like three minutes flat. If my band's career had to be summed up in one song? This would be it.

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Ice Cube, “Amerikkka’s Most Wanted” (1990)

As we celebrate the victory that is Watch the Throne, we will notice that most joint collective hip-hop albums have been underwhelming. (Best of Both Worlds? The Firm, anyone?) Most will note that this pairing of Public Enemy's Bomb Squad & N.W.A.'s best MC was the best, and somewhat first, such summit meeting in hip-hop. If this were an albums list, this title cut and its album would gain instant top 10 status. Even though Cube has more iconic singles, the drummer in me selfishly chose this song simply because it has the best, most violently disturbing use of a hi-hat sample chop in hip-hop. Always on the cutting edge, the Squad skipped the solid drum break of Kool & the Gang's "Let the Music Take Your Mind" and actually looped the more colorful drum solo instead. Undoing James Brown's rule of "You ain't got to do no soloing brother, don't turn it loose!!!!" Yet somehow the panic of it all only added to Cube's fury. Man, it was a mother!

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Boogie Down Productions, “The Bridge Is Over” (1987)

The best example of a song from the crew that introduced dancehall reggae ideas into the mix. Kris' albums were so radical and ahead of their time, it's easy to overlook the power of his singles. But make no mistake, he led the post-modern charge of innovation that would be forever known as the classic era of the culture.

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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!

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Cypress Hill, “How I Could Just Kill a Man” (1991)

In 1991, Public Enemy's Bomb Squad production team imploded, and along with it the freedom to sample any sound source without legal ramifications. The producer to make the best of the Squad's remains was Cypress Hill's DJ Muggs. He mostly took their "use everything but the kitchen sink" mission and refocused it to late Sixties rock and blues loops and a muddier soundscape with accessory noises used for psychedelic effect. Of course, the best trait taken from Strong Island's finest was the chemistry between B-Real's nasal flow and Sen Dog's rough gruff. Bucking fools down never sounded so fun.

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Black Sheep, “The Choice Is Yours (Revisited)” (1991)

In hindsight, I'm sure that Black Sheep really thought they were the N.W.A. of the alt-hip-hop collective Native Tongues. To me, they were more animated and esoteric than their alt-hop brethren – who, ironically, were more center to the right than they actually thought they were. I'mma say straight up, this is the best, most effective remix/facelift hip-hop has ever seen. I mean, the original was a mother as-is. The amount of innovation created in 1991 was staggering. Like, every other song was changing lives. And every single was made trying to one-up what came before it. Because of the jazz floodgates that were opened with Tribe's Low End Theory album, the resulting effect was that an upright bass gave you more "umph!" than a TR-808 drum machine could. So everyone was going jazzy: Onyx, Digable Planets, Pharcyde, Showbiz & AG . . . everyone. But there can only be one winner, and that winner lay somewhere between the opening bass drop of this single and Dres' last verse. Even to this day, everyone bends to the floor recreating its infectious video, only to explode jumping for joy like it was hip-hop's "Smells Like Teen Spirit." Men, women and dancing hamsters in Kias cannot be wrong.

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Bone Thugs-N-Harmony, “Thuggish Ruggish Bone” (1995)

I'll admit it. Die-hard East Coasters, with our snobby dispositions – having been in the audience during the hip-hop civil war, a.k.a. the 1995 Source Awards – weren't too quick to let Bone Thugs in the door. Which is rather strange, considering our embrace of the art of harmonizing – see The Fantastic Romantic 5, The Force MCs, The Cold Crush Brothers – and the tongue-twisting style that Das EFX introduced some three years before Eazy-E brought his Bone Thugs proteges to the forefront as his last act before his passing in 1994. This song made their follow-up "1st of tha Month" possible, which then was the prefect setup to their mammoth "Crossroads," which thus gave birth to the most effective summit meeting hip-hop has witnessed: '97's "Notorious Thugs," for B.I.G.'s Life After Death opus. That moment freed stubborn East Coast devotees to embrace "Big Pimpin'" all the way to "Niggas in Paris." My first moments of skepticism in hip-hop were with how to deal with this new direction that hip-hop was going in that clearly I was afraid to go. (See: Change scares all types of people.)

The strangest twist of this tale is that it took another super-summit meeting of the minds to contextualize my newfound respect of Bone Thugs: Jazz scat master Jon Hendricks pairing riffs with Bobby McFerrin, George Benson and Al Jarreau for an awesome version of "Freddie Freeloader." Suddenly, from a jazz perspective, I saw the light and became a convert of East 99th's finest for life.


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Common, “I Used to Love H.E.R.” (1994)

'94 marked a year of growing pains for fans of hip-hop. For all of those post-civil-rights kids who were 10 when hip-hop went national, it had been like welcoming a new pet in the family, or a lil' sister, or even your first schoolboy crush. Now, some 14 years later, that pet ain't the same ol' chum that you spent your childhood with. Your lil' sis wants her own space. And your crush now wants to hold hands with Jamal in the ninth grade, leaving you in the cold. You get older. They get older and most likely move on to another place in time. Common dealt with his bewilderment in the sweetest way possible: a Dear John letter. This was hip-hop's version of Bill Withers' "Ain't No Sunshine." Nice how a goodbye letter actually winds up immortalizing one of the most gifted MCs in our culture – thus ensuring her memory forever.

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Grandmaster Flash and the Furious Five, “White Lines” (1984)

LL Cool J once told me his grandparents forbade him from nicknaming himself J-Ski for "obvious reasons." I tried to go along, but the 40-year-old virgin in me had to reveal I wasn't as cool as I thought I was. Backstage at Fallon, I was like, "I don't get it." He explained to me that "ski" represented "snow." It took 15 seconds, but I was like, "Oh!" Then I went through all of the "cold" name references in hip-hop and asked him, "Wait . . .  so all of those rappers were just code names for those that chose 'coke' names? Kool Rock Ski? Joe Ski Love? Kurtis Blow?" He just laughed. Boy, was I naive.

The first generation of rappers ('72-'82) were now seeing the setbacks of what seemed like a harmless hobby enhancer. The mid-Eighties offered nothing but crash and burn options. So for a charter member of the "blow generation" to offer up an anti-drug song – way before the "just say no" madness started and two years before the crack epidemic destroyed lives – that was a mighty statement. To slyly point out the hypocrisy of the Rockefeller laws on inner city poor versus white collar crimes was even bolder. I later found out that Mel was still caught up in the white madness while doing his vocals. That, to me, is the craziest. Cocaine was a hell of a drug.

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BCM Records


DJ Mark the 45 King, “The 900 Number” (1988)

The 45 King gained his greatest fame as the architect of Eminem's finest hour: "Stan." But those in the know can tell you Mark created the national anthem of hip-hop, a James Brown-related horn loop that will never die. So simple and completely made of magic. Most don't even know this is an instrumental to an actual rap. But it's so potent it needs nothing but humans with a pulse. I swear I've never, ever, ever seen this record fail. Twenty-five years old, and still sounds fresher than fresh.

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Naughty By Nature, “O.P.P.” (1991)

Jersey's own Naughty by Nature was a rarity in hip-hop: an urban pop act that held respect and dignity in the Nineties. To go platinum in hip-hop, you were either diluted for mass consumption, or an overdone cartoon image of gangsterism that was temporary. Naughty By Nature chose the equivalent of shooting three-pointers from half-court: pop classics. Only Prince, MJ and Stevie had the ability to create pop-friendly songs without losing themselves in the process. That was a slippery slope to walk. Treach was just as respectful an MC as the best of them, and Kay Gee made sure that his infectious musical elements didn't crowd his grit and dusty breakbeats. But of course, when the Jackson Five's "ABC" was your template, can you really drop the ball? 

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Big Daddy Kane, “Raw” (1988)

When cats my age are reminiscing on "the classic hip-hop period" when so-and-so and such-and-such was as good as it gets – you know, when that Wayne's World dream sequence starts? This is the song that plays in our heads when we think about when hip-hop was at its apex. Beats and rhymes. Simple as that, but complex as hell.


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Digital Underground, “The Humpty Dance” (1990)

One of the most potent, re-useable, powerful snares in Nineties music. You'll stop counting at 200 if you try to take a total of how many songs between 1990 and 2003 just straight-up took this track's drum ingredient. Like, seriously, this song is the two fish and five loaves of bread of hip-hop. No organization represented George Clinton's P-Funk rhythm nation better than Shock G and Co.

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Craig Mack, “Flava In Ya Ear (Remix)” / The Notorious B.I.G., “Juicy”/”Unbelievable” (1994)

Amazing that the two singles that started an empire – one deemed "the beginning of the end of underground hip-hop" by purists – were two of the best underground-approved debuts in hip-hop history. First time I ever heard a DJ spin a record five times in a row like he didn't give a shit was "Flava in Ya Ear." This was when I was living in London, so I know America was going crazy. I'd do the same, too. Some of the most powerful hip-hop songs had elements so simple your brain would explode trying to explain their logic. It took Easy Mo Bee almost 17 years to finally reveal his sound source for the two note guitar stab on "Flava." I wanted to throw someone out the window, Axel Foley style, when I realized I had the answer all along and couldn't figure it out for myself. (And yes, I'm sworn to secrecy.)

B.I.G.'s "Juicy" set a new template for NYC with its aspirational rags-to-riches vision – Jay-Z's "I made it!!!" calling card. Taking a cue from Dr. Dre, Sean Combs' Hitmen gave Big a cleaner, afternoon-format-friendly music to counter-attack the "more music, less rap!" defense that urban radio tried to roll with since rap's origin. The song hit jackpot and soon every MC's "rebel, renegade, must stay paid" period began.

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Wu-Tang Clan, “Protect Ya Neck” (1993)

"Protect Ya Neck" is the purest uncut entry on this entire list. There is no hook. No bridge. No easy to remember melody. Which really demonstrates the magic that a five-minute catalogue display works on all levels based on charm and cleverness. In my opinion, Wu-Tang was the smartest boy band: the battler, the street smart, the heartthrob, the hood, the crazy one, the charming schizophrenic, the wise sage, and yes –the genius. They dropped more pop culture references than the beastie boys. Movie quotes, Broadway showtunes, cartoon references, soul quotes. When my cousins and neighborhood friends would have sleepovers at grandma's on Saturday, the order of each one who woke up earliest got priority seating for the color TV and got first rights to claim which superfriend they were that day. (I was always last and was left either claiming Wendy and Marvin, or worse, Wonderdog.) I imagine the Clan woulda been us had we grown up together and started a business in which all of our childhood experiences and memories were a marketable franchise. Sadly, this single represents a closing chapter for hip-hop as well: This would mark the last time hip-hop so uncut was successful. Can it be that it was all so simple then?


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LL Cool J, “I Need Love” (1987)

Back before Internet leaks, the music industry primarily followed the rules for the most part. Records were created and distributed to radio and the press some three months before their actual release dates. That way, a proper buzz could work its magic. And unless you were super-connected, you really didn't worry about bootlegging – well, until late 1987, and only hip-hop suffered. I had an inside connect with a record store owner that was also a part-time reporter for Billboard magazine. He would get promo press copies of stuff way in advance. Early '87, while shopping, he told me he got a press copy of the new Bigger and Deffer sophomore LP from LL. I begged and begged for a copy. He told me he'd dub it and to pick it up the following Monday after school.

That Monday, it was on. My Sony Walkman was never happier. I was stuck on side one, tryna figure out which of L's verses I was gonna bite and claim as my own creation in case a lunchroom cipher was gonna jump off. Most of side one was narrative stuff with specific story lines, and the two battle raps were already singles. So then I went to side two: a "Johnny B. Goode" remake, a dis track with too many LL references and curse words that I knew no one would believe I came up with myself – and then it happened. That cheesy Yamaha DX-7 bell patch: "When I'm alone in my room, sometimes I stare at the wall . . . " (Yeah, I stare at the wall, too! Mainly at that Whitney poster, but I stare!!!) ". . . And in the back of my mind I hear my conscience call . . . " (Yeah, yeah, LL, me too!!! Me too!!!!) ". . . Telling me I need a girl as sweet as a dove/And for the first time in my life? I see I need love." YO!!!! Later for that geometry exam! I found the LL rhyme that was gonna catapult me to the stars. I thought that I needed about five battle verses to whup someone with during lunch just to impress the girls. But LL done wrote a song that I can use to cut the middle man out and go straight for the prize!

Did I dare think this song would be his calling card to a triple-platinum plaque and stardom beyond his imagination? Of course not. It ain't like radio was gonna play a rap love song in the afternoon, right? No one is gonna ever hear this song in the real world, 'cause only certain cats like me like this obscure stuff . . . right? I'mma write these lyrics down right now (I failed that geometry quiz) and she will fall in love (she sorta did, for five weeks at least) and cherish this new poem I wrote for her called "I Need Love." That worked until radio jumped all over it like a new gang member initiation. Yeah, she made me the laughing stock of her mean girl high school crew, and it took a while for the laughter to die down. But she follows me on Facebook. So now I'm getting the last national laugh!

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Geto Boys, “Mind Playin’ Tricks on Me” (1990)

This is what can happen if you just dial it down by 1000. Houston's Geto Boys first got our attention when Chuck D gave 'em a shout-out on Fear Of A Black Planet. Then they spent the entire summer of 1990 playing the press piñata of extreme shock rap. I mean, okay, I copped their debut and was more amused at their cartoon flow than afraid of them. America was all, "The youth are going to hell for listening to this ruckus!" Man, I was doing nothing but laughing. All that changed with this single. They lost the extremism and played it more to the middle, with chilling deadpan perfection. As a result, this is an awesome complex display of paranoia, and somehow manages to add a third dimension – which of course humanizes them in the end.


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Schooly D, “P.S.K. What Does It Mean?” (1985)

Thanksgiving 1985. I was 14 years old. It was 10 p.m., and I was tuned into Power 99 FM. Then it came on: the sound of a Roland 909 coming through what sounded like a church cathedral eight city blocks big. That much echo. I was more hypnotized at the way the drums kept coming in off-beat at the top of each phrase ending. This was the second phase of the blues, because there was a structure similar to how the blues was structured: blues gave us 1/4/5/1 chord structure. "P.S.K." was modeled the same way: First establishing line ("Got to the place and what did I see?"), second observation line ("Some sucker ass nigga tryna sound like me"), main action ("Put my pistol up against his head"), then the payoff line ("I said, 'Sucka ass nigga, I should shoot you dead'")! This was unprecedented. Absolutely unprecedented.

This single made the entire Licensed To Ill album possible. The Beasties followed the same Schooly blues formula: 1. "I got money in the bank, I can still get high," 2. "That's why your girlfriend thinks that I'm so fly," 3. "I got . . . twin sisters in the bed," 4. "Their father had envy, so I shot him in the head." That formula is what birthed the loveable genre of gangsta rap. N.W.A. just took the formula and ran with it.

I found out a bit of side trivia when I happened to work with Jeff Cheesesteak, the engineer of "P.S.K." He told me since no one had read the manual of the 909 drum machine, no one knew how to sequence it. So in one take, Schooly stood at the microphone and pressed the buttons himself as he did the rhyme. As a fellow Philadelphian, I couldn't have been more proud. A classic example of how my town of Philly was full of innovators. That's what it really means. 

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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 col