The 50 Greatest Hip-Hop Songs of All Time - Rolling Stone
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The 50 Greatest Hip-Hop Songs of All Time

Jay Z, Eminem, Tupac, Biggie and more

Jayz Eminem Tupac Shakur Notorius B.I.G

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Looking for the full list of the 100 greatest hip-hop songs of all time? Check it out right here.

Editor’s note: To make this list, Rolling Stone asked 33 artists and experts – from Rick Rubin to Busta Rhymes – to choose their favorite hip-hop tracks, then crunched the numbers. Click to read the full list of voters.

What Makes a Great Hip-Hop Song?
An Introduction by Ahmir “Questlove” Thompson

I was eight years old when “Rapper’s Delight” made its world premiere on Philadelphia radio. It happened at 8:24 p.m. on a Thursday, 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 washing 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.” How was I to know that my world would come crashing down in a matter of 5, 4, 3, 2 . . .

I said a hip, hop, the hippy to the hippy/To the hip hip hop, you don’t stop. . . .

The next night, I was prepared, with a prehistoric tape recorder in hand and a black-and-white composition notebook. My boy Aantar became my agent that week, scheduling performances of the song in exchange 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.

Some of the most powerful hip-hop songs are tracks with elements so simple your brain would explode trying to explain their logic: Take the unstoppable two-note guitar stab in Craig Mack’s “Flava in Ya Ear.” (I hounded the producer, Easy Mo Bee, for 17 years for the secret behind it – then wanted to throw someone out the window when I heard how basic it was.) Or the huge sound of the Roland 909 on Schoolly D’s “PSK” – an echo that seemed like it came from a church cathedral eight city blocks wide.

These sounds had incredible power if you grew up with hip-hop: There was the summer I spent trying to match the mix to “The Adventures of Grandmaster Flash on the Wheels of Steel,” note for note, on two Fisher-Price turntables. (My father, unimpressed, told me, “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: in the high school lunchroom when me and Black Thought heard “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.

Hip-hop gives listeners sets 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”) to now (“What the fuck was that?!“). I’ve seen Vanilla Ice’s “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.

The greatest hip-hop songs have the power to pull energy and excitement and anger and questions and self-doubt and raw emotion out of you. It could be a song that sets your neighborhood on fire (“Rebel Without a Pause”) or a song on your headphones that makes you rethink what hip-hop is (Ultramagnetic MCs’ “Ego Trippin’ ”). The common thread is change. The best hip-hop songs aren’t blueprints – they are calls to action, reminders that you can start a revolution in three minutes. Just keep that clock radio on.


Outkast, ‘B.O.B’

Stankonia, 2000

Outkast greeted the 21st century with a single that’ll probably still sound ahead of its time in the 22nd: Big Boi and Andre 3000 air millennial anxieties over a genuinely insane beat of jackhammer drums, Hendrix-at-Monterey guitars and massed voices chanting “Power music, electric revival” like a gospel choir conducted by Afrika Bambaataa.


Grandmaster Flash and the Furious Five, ‘Adventures of Grandmaster Flash on the Wheels of Steel’

Non-album single, 1981

Using three turntables and a crossfader (a device he invented), 23-year-old Flash created a continuous party jam out of records by Chic, Blondie, Queen and more – showing off frenetic steel-wheels moves and establishing the DJ as a new kind of pop musician.


Marley Marl, ‘The Symphony’

In Control, Volume 1, 1988

Wizardly producer Marley Marl dials up a beat for the ages – a ferocious drum break and Otis Redding piano loop – and summons the cream of his Juice Crew affiliates. The result is the first truly great posse cut. Sharpest couplet: Kool G Rap (“Making veterans run for medicine/’Cause I put out more lights in a fight than Con Edison”). MVP: Marley Marl.


Funky 4 + 1, ‘That’s the Joint’

Non-album single, 1980

Nearly 10 minutes and God knows how many bars of exhortations and boasts, sprawling across a hopped-up disco beat. Doug Wimbish’s bass breakdown is as funky as anything this side of Bootsy Collins. But the real star of the show is the Funky Four’s “plus-one woman,” Sha-Rock (a.k.a. Sharon Green), the first female MC featured on a hit rap record.


Salt-N-Pepa, ‘Push It’

Hot, Cool and Vicious, 1986

Salt-N-Pepa’s libidinous jam was one of the first rap records to top the dance charts, and it remains as dependable a party-starter as any song of the hip-hop era. The snake-charmer electro groove is a monster and Cheryl “Salt” James and Sandy “Pepa” Denton trounce all comers in the man-strafing sassiness department: “Can’t you hear the music’s pumpin’ hard like I wish you would?” they rap. Joke’s on you, fellas.


Lauryn Hill, ‘Lost Ones’

The Miseducation of Lauryn Hill, 1998

The opening track on Hill’s landmark solo debut album is a reminder of how viciously this great singer could rhyme. It was recorded in Jamaica, and Hill raps (and, in the chorus, croons) in her version of a Trenchtown patois; “Lost Ones” sounds like a spit-roasting indictment of her former Fugees bandmate and ex-lover Wyclef Jean, who must’ve been quaking in his Timbs.


De La Soul, ‘Me, Myself and I’

3 Feet High and Rising, 1989

Urged by label brass to provide their adventurous debut album with a song that wouldn’t be “so over someone’s head,” De La Soul concocted a cosmically inclusive house-party jam. Producer Prince Paul threw down an exemplary Funkadelic beat and the rappers dropped a buoyant lyrical statement of purpose: “De La Soul is from the soul.” This song proved that the three guys knew how to rock the body, too.


Audio Two, ‘Top Billin”

What More Can I Say?, 1988

Rhyming over nothing but the drum break from Honeydripper's "Impeach the President," Kirk "MC Milk Dee" Robinson shouts out his parents, his hood, his DJ-brother Giz and his bodyguard, sounding like he might laugh, kick your ass or both. Variations on the hook – "Milk is chillin', Gizmo's chillin'/What more can I say? Top billin'!" – have been spit by MCs from Dre to Biggie to Jay-Z. By now, it's hip-hop bedrock.


Boogie Down Productions, ‘South Bronx’

Criminal Minded, 1987

Kris “KRS-One” Parker of BDP was one of early rap’s most authoritative voices, and this story of hip-hop’s early days is a required master class. DJ Scott LaRock threads a hot James Brown sample and KRS recalls a golden age when his borough reigned supreme; “South Bronx” was a bow shot in a diss war between BDP and Queens’ Juice Crew that set the standard for all regional beef-fests.


2Pac and Dr. Dre, ‘California Love’

Non-album single, 1995

Tupac Shakur‘s biggest hit was a celebration, marking the rapper’s release from prison (“Fresh outta jail, California dreamin'”) with a “serenade [to] the streets of L.A.” It was Dre‘s beat, though, that brought the sunshine: a buoyantly funky party groove, with delicious vocodered singing from Zapp frontman Roger Troutman – a premonition of the Auto-Tune mania that would sweep hip-hop a decade later. 


Kurtis Blow, ‘The Breaks’

Non-album single, 1980

The first rap hit on a major label, peaking at Number 87, was a no-frills joint: a loping bass line and jumping beat with the Harlem-born Blow presiding over playground-party noises and percussion breakdowns. Blow toured extensively behind "The Breaks," taking B-boy culture to mainstream USA while blazing a trail for rappers like Run of Run-DMC, who got his start billing himself "The Son of Kurtis Blow."


Eminem, ‘My Name Is . . .’

The Slim Shady LP, 1999

“God sent me to piss the world off,” announced Eminem on his debut single. Mission accomplished: Over Dr. Dre‘s brisk, cartoon-funk beat, Em tears off Pamela Anderson’s breasts, goes after his junior-high English teacher’s nuts with a stapler and rhymes “head straight” with “impregnate.” He was something truly new: a Midwestern trailer-park kid with serious issues and an endless supply of uproarious rhymes.


Missy Elliot, ‘Get Ur Freak On’

Miss E . . . So Addictive, 2001

In the late Nineties and early Aughts, Missy Elliott and Timbaland were pop’s greatest mind-benders, and “Get Ur Freak On” is their funkiest, nuttiest moment. The beat takes hip-hop Orientalism to outer space as Missy hisses, squawks, stutters (“I sw-sw-switched my style”), bellows commands (“Silence!”) and delivers the greatest hocked loogie in the history of recorded sound.


Ice Cube, ‘It Was a Good Day’

The Predator, 1992

Ice Cube‘s biggest hit is a ghetto pastorale, forsaking violence to revel in good vibes and a plush Isley Brothers sample. Cube eats a fine breakfast, smokes his homeys on the b-ball court, then smokes some chronic with a hottie and doesn’t have to use his AK-47 once. Day: made.


Outkast, ‘Rosa Parks’

Aquemini, 1998

The song that made everyone fall in love with Outkast was a deceptively deep party jam, with Big Boi and Andre 3000 showing off flows as smooth as Georgia molasses. Rosa Parks brought a lawsuit for misappropriating her name, but by then this hit had brought Southern tang to the rap charts.


Mobb Deep, ‘Shook Ones Part II’

The Infamous, 1995

Dedicating their signature track to “all the killers . . . for-real niggas who ain’t got no feelings,” this New York duo cooked gangsta rap down to its inkiest, most nihilistic essence. A snippet from a Quincy Jones soundtrack infuses the song with a sinister hiss. Prodigy promises that his “gunshots will make you levitate,” taking time to remind you that he’s “only 19,” too. All these years later, you still ache for that kid. 


Schoolly D, ‘P.S.K. What Does It Mean?’

"This birthed gangsta rap," Questlove said. "N.W.A just took [its] formula and ran with it." The Philly MC got his track's name from a gang, Park Side Killers, and its beat from an evidently stressed-out Roland 909 drum machine. In a lazily menacing flow, he buys coke, beds a whore, buys weed and flashes a pistol. That he decides not to pull the trigger makes the jam no less chilling.


Jay-Z, ’99 Problems’

Rick Rubin brought his OG magic out of storage to make one of the most explosive beats in rap history, setting body-slam power chords over the drums in Billy Squier’s “The Big Beat.” Jay-Z concocts an indelible pop chorus and sketches out a scene based on an encounter with a racist patrolman from his pre-stardom days. As Jay wrote in his memoir, “The first offense wasn’t the crack in the ride but the color of the driver.”


Kanye West, ‘Jesus Walks’

The College Dropout, 2004

Kanye has never been shy about his God complex, but humility, not hubris, made “Jesus Walks” hip-hop’s finest gospel testimonial. The production is stunning – built on a sample of a Harlem choir cresting above a martial beat – as West avoids easy pieties and raps about spiritual hunger and self-doubt. “Kanye proved to me he can be Marvin Gaye,” said Chuck D. “‘Jesus Walks’ touched on an area no one else had, lyrically.”


Nas, ‘N.Y. State of Mind’

Illmatic, 1994

No track better sums up Nas‘ ability to spin dense, dazzlingly lucid verse. “N.Y. State of Mind” is no anthem or ode to the city; it’s a detailed narrative about a Gotham gunfight, delivered in a nearly 60-bar run that Nas later broke up for the song. “He did the whole first verse in one take,” recalled DJ Premier, who produced the track. “He stopped and said, ‘Does that sound cool?’ And we were all like, ‘Oh, my God.’ ”


Notorious B.I.G., ‘Hypnotize’

Life After Death, 1997

“Hypnotize” was Biggie‘s greatest pop moment, topping the charts weeks after his murder in March 1997. Delivered over Puff Daddy’s Herb Alpert­-sampling candy-corn beat, it showed his knack for leavening gangsta sex and violence with punch lines even a toddler could cuddle up to: “Poppa been smooth since days of Underoos,” he quipped. No one’s been smoother since.

LL Cool J

LL Cool J, ‘Mama Said Knock You Out’

Mama Said Knock You Out, 1990

“Don’t call it a comeback!” begins rap’s hottest-ever comeback. After crossover pop success, James Todd Smith returned to street-fighting hip-hop pledging to “bash this beat like a skull,” and returning fire from a Kool Moe Dee diss record. The beat, one of Marley Marl’s best, rides a four-count chant from Sly and the Family Stone‘s “Trip to Your Heart,” and the track peaks with J repeating, “Damage! Damage!” like he’s done rhyming and is ready to break shit.


Eminem, ‘Lose Yourself’

‘8 Mile’ soundtrack, 2002

Eminem‘s biggest-ever hit plays like Rocky condensed into a five-minute song. It helped that in telling the story of Rabbit – the trailer-dwelling aspiring rapper he played in 8 Mile – Eminem was more or less telling his own, sidestepping demented clowning and pure rage in favor of tough, realist rhymes about overcoming very long odds. Em cut the song during a brief break from filming. “He came in and laid down all three verses in one take,” recalled engineer Steven King. “Jaws dropped – we were like, ‘Oh, my God!’ This story had been building up in him.”


Craig Mack, Rampage, the Notorious B.I.G., LL Cool J, Busta Rhymes, ‘Flava in Ya Ear (Remix)’

Non-album single, 1994

Craig Mack has faded into obscurity – reportedly renouncing rap to join a fundamentalist Christian cult in South Carolina – but he left his mark on rap history with his debut single and its remix, one of hip-hop’s greatest posse cuts. Mack’s verse has its moments – “Wanna grab my dick/Too lazy/Hold it for me” – but the real fireworks come from the guests: a suave, sexy LL; Busta Rhymes, nearly devouring the mic in a manic 20 bars; and, above all, the punch-line-slinging Biggie Smalls, stealing the song right out from under his Bad Boy labelmate, beginning with one of his funniest boasts: “Niggas is mad I get more butt than ashtrays.”

a tribe called quest

A Tribe Called Quest, ‘Scenario’

Q-Tip, Phife Dawg and Ali Shaheed Muhammad cultivated a reputation as bohemian jazzbos, but they made one of their best songs when the incense smoke cleared, and they got into b-boy mode – slinging tight rhymes over a wicked downbeat. This meeting between Tribe and Leaders of the New School is one of rap's most exciting oddball summits. Everyone brings his A-game, with top honors going to Tribe's punch-line specialist, Phife: "Short, dark and handsome/Bust a nut inside your eye, to show you where I come from." "Scenario" is most famous for the breakout performance by 19-year-old Busta Rhymes, who comes out roaring like a dungeon dragon. "I thought he was ill," Q-Tip later said. "I just wanted to set him up."


Big Daddy Kane, ‘Ain’t No Half Steppin”

Long Live the Kane, 1988

When Jay-Z christened Brooklyn’s new Barclays Center arena earlier this year with a series of eight straight shows, he brought out only one guest rapper to share his stage: Bed-Stuy native Big Daddy Kane. And for good reason. Antonio Hardy was the master wordsmith of rap’s late-golden age and a huge influence on a generation of MCs. On “Ain’t No Half Steppin’,” his tone is rich and commanding as he rocks tightly coiled extended metaphors over Marley Marl’s laid-back groove (based around the Emotions’ fine 1972 cut “Blind Alley”): “Rappers, you better be/Ready to die because you’re petty/You’re just a butter knife, I’m a machete.” Legend has it that even the Eighties’ greatest rapper, Rakim, turned down a challenge to go mic-to-mic with Kane.


Rob Base and DJ E-Z Rock, ‘It Takes Two’

It Takes Two, 1988

“All I know is, it’s a club banger,” Rob Base said of his biggest rec­ord. Actually, it’s the mother of all club bangers, a pop-rap opus that’s as absurdly fun today as it was 25 years ago. Mixing hip-hop and house music, lifting liberally from James Brown background singer Lyn Collins’ 1971 song “Think About It,” Rob Base and DJ E-Z Rock’s 1988 smash was also an ode to understanding and respect, one that brought everyone together under a groove – from block parties in Harlem to slumber parties in Des Moines. The song was produced by Teddy Riley, who deployed a similar jump-up syncopation as the king of New Jack Swing. Base later said, “I wanted people to get up and dance and not have to worry about fightin’ and arguin’.”


Eric B. and Rakim, ‘I Know You Got Soul’

Paid in Full, 1987

“When I’m writing, I’m trapped between the lines/I escape when I finish the rhyme,” explains Rakim, rocking the kind of jam that would soon disappear once copyright lawyers stepped up their game. Eric B. looped a chunk of the James Brown-produced song of the same name by Bobby Byrd and the J.B.’s All Stars. But all turnabout is fair play: The British mix masters M|A|R|R|S constructed their hit “Pump Up the Volume” around a sample of Rakim saying that memorable phrase on “I Know You Got Soul.”


EPMD, ‘Strictly Business’

Strictly Business, 1988

The greatest thing about EPMD’s inaugural single is the duo’s self-produced beat – a cornucopia of blatant samples from the golden age of artistic pilfering, with Eric Clapton’s “I Shot the Sheriff” busting wild-style moves on the floor next to Mountain and Kool and the Gang. Erick Sermon and Parrish Smith’s laid-back rhymes were revolutionary in their way too. Most rappers in 1988 were still stuck on loud, clear cadences. EPMD’s casual, goofy approach to the mic laid the groundwork for generations of chilled-out – as well as weeded-out – rappers. 


LL Cool J, ‘Rock the Bells’

Radio, 1985

Leaping off a rock-hard riff from AC/DC‘s 1983 scorcher “Flick the Switch” (also tapped for the Beastie Boys‘ “Slow and Low”), Long Island teenager James Todd Smith calls out every rapper in town, disses Michael Jackson and Prince, dismisses Bruce Springsteen and pledges to “make Madonna scream.” His flow is so scene-chewingly hungry, you don’t doubt him for a minute. The third single from his debut, Radio, is Rick Rubin’s remake of an early 12-inch version that in fact had bells (the same ones that show up on Run-DMC‘s Rubin-produced “Peter Piper”). But this one rings even louder. It’s a rap Rosetta stone quoted to this day. LL liked it so much he went ahead and sampled it himself on his equally crushing 1991 single “Mama Said Knock You Out.”


50 Cent, ‘In Da Club’

Get Rich or Die Tryin’, 2003

“We just made some shit we wanted to hear,” producer Dr. Dre told Rolling Stone in 2003. “As soon as 50 walked in the studio, he picked up a pen and we were done in an hour.” Queens native Curtis Jackson had it all: an almost mythic backstory (he was a genuinely talented thug who’d once taken nine bullets), the backing of Dr. Dre and Eminem, and a lush, languid flow that sucked you in, no matter what he was saying. All he needed was a monster beat to elevate him from squinting antagonizer to club sultan; over the most clinically precise hand claps and synths ever to grace a rap record, he sent everyone with a pulse hurtling toward the dance floor while threatening to “put the rap game in a choke hold.” By the time this hit Number One, he had.

beastie boys

Beastie Boys, ‘Paul Revere’

Licensed to Ill, 1986

Michael “Mike D” Diamond remembers when Adam “MCA” Yauch hit on the squishy beat that propels this crackling single – by running the tape backward. “We were as giddy as kids, yelling in the studio,” Diamond says. “It was the simplest idea, and he killed it.” The lyrics are a fictional spaghetti-Western-style account of how the Beasties met, recounted by Adam “Ad-Rock” Horovitz as Diamond and Yauch butt in and out with argumentative glee – a prime example of the Beasties’ frisky interplay. One rhyme about a girl and “a Wiffle-ball bat” got them in hot water for misogyny. The Beasties would back off from that kind of verse as they matured. But they performed “Paul Revere” right to the end: at Bonnaroo in 2009, Yauch’s last show before his passing this year.


2Pac, ‘Dear Mama’

Me Against the World, 1995

“The emotional, the sad songs, were his personal favorites,” said Johnny J, one of the late Tupac Shakur‘s producers. There was always a plaintive side to 2Pac’s thug-life tales, and he foregrounded the pathos on his 1995 ballad tribute to his mother, Afeni Shakur. The song is the ne plus ultra of hip-hop odes to Mom. Tony Pizarro’s beat, with its plush Seventies soul samples, sets a tender mood, and the rhymes strike a similar note: “I appreciate how you raised me/And all the extra love that you gave me.” But “Dear Mama” hits harder for its warts-and-all realism, as 2Pac doesn’t shy from describing his own failings, his pain over his absent father and his mother’s struggle with drug addiction: “And even as a crack fiend, Mama/You always was a black queen, Mama.”



Run-DMC, ‘Peter Piper’

Raising Hell, 1986

The opening track on Run-DMC’s 1986 classic, Raising Hell, is still the greatest ode ever to the Midas-like powers of a DJ. Jam Master Jay sliced up Bob James’ bell-ringing 1975 smooth-jazz version of “Take Me to the Mardi Gras” as Run and DMC summed up their partner’s greatness: “Not bad meaning bad but bad meaning good!” Run-DMC’s label, Profile Records, wanted “Walk This Way,” a rap-rock collaboration with Aerosmith, to be the first single off their new album. But the group was adamant that “My Adidas”/”Peter Piper,” odes to hip-hop culture, be the first release; Darryl “DMC” McDaniels later recalled saying, “If y’all don’t do it, we’re gonna give it to the radio and fuck everything up.” They prevailed, and Raising Hell became rap’s first blockbuster album.

jay z

Jay-Z feat. UGK, ‘Big Pimpin”

Vol 3 . . . The Life and Times of S. Carter, 1999

Jay-Z has since said he’s a little ashamed by the rawness of his tricky verses on “Big Pimpin'” – “I thug ’em, fuck ’em, love ’em, leave ’em/Cause I don’t fuckin’ need ’em,” the future family man and business leader boasts. But “Big Pimpin'” is the ultimate playa anthem. Jay defied regional bias by reaching across the Mason-Dixon Line and giving Port Arthur, Texas, duo UGK a prominent spot on one of his biggest hits. And Timbaland’s beat was just as ecumenical – a bugged-out orchestral track from Egypt that deepened the song’s sense of world-straddling dominance.


N.W.A, ‘Fuck tha Police’

Straight Outta Compton, 1988

The pivot point between Public Enemy‘s Black Panther revivalism and gangsta rap’s nihilism, this hard-funk assault indicted the L.A.P.D. and seemed like prophecy in the L.A. riots/Rodney King era. “Fuckin’ with me ’cause I’m a teenager/With a little bit of gold and a pager,” rhymes Ice Cube, who was 19 when the song was released, adding, “When I’m finished, it’s gonna be a bloodbath of cops/Dyin’ in L.A.” The FBI took it seriously enough to send a warning letter to N.W.A‘s label that alleged the song “encourages violence against, and disrespect for, the law enforcement officer.” The publicity established N.W.A as hip-hop’s number-one bad boys.


Public Enemy, ‘Rebel Without a Pause’

It Takes a Nation of Millions to Hold Us Back, 1988

Opening with a Jesse Jackson sample (“Brothers and sisters, I don’t know what this world is coming to!”) and upping the agit-pop ante with Chuck D’s broadcaster-baiting (“Radio/Suckers never play me”), this 1987 single perfected PE‘s hand-grenade attack. “A statement of purpose for the PE to come,” says Rick Rubin. The signature siren squeal is a looped horn from the JB’s 1970 obscurity “The Grunt,” the groove grabs James Brown‘s “Funky Drummer” and Terminator X scratches the chorus of Chubb Rock’s “Rock ‘N Roll Dude” (“We use samples like an artist would use paint,” said co-producer Hank Shocklee). When Chuck D heard the finished track, he was so stoked he said, “I could die tomorrow.”


Doug E. Fresh and the Get Fresh Crew, ‘La Di Da Di’

Non-album single, 1985

Eye-patched British-American rapper Slick Rick was still known as MC Ricky D when "La Di Da Di" was released in 1985. He spins a Mrs. Robinson tale of being hit on by his ex-girlfriend's mom, while beatbox pioneer Fresh provides backdrop. A milestone in rap storytelling (and product placement: Gucci, Bally, Kangol, Polo, Johnson's baby powder and Oil of Olay), it would be referenced endlessly, most famously in the chorus of the Notorious B.I.G.'s "Hypnotize," and most thoroughly in Snoop Dogg's "Lodi Dodi," a weed-obsessed cover version. It also began the trend of rappers breaking into off-key song – although Rick's detour into A Taste of Honey's "Sukiyaki" was later edited out for copyright reasons.

Pete Rock, C.L. Smooth

Pete Rock and C.L. Smooth, ‘They Reminisce Over You (T.R.O.Y.)’

Mecca and the Soul Brother, 1992

Hip-hop's most beautiful elegy: The early-Nineties duo wrote the song for their childhood friend Trouble T-Roy, a dancer with Heavy D and the Boyz who died after falling off a stage in 1990. Over a tender, sky-blown sax sample from Sixties jazz-pop composer Tom Scott, rapper CL Smooth spins a tribute to his fallen friend into a vivid celebration of family (literal and metaphorical) that's as much free-roaming backyard-barbecue toast as somber funeral speech. When producer Rock first played the finished track, "we just started crying." Andre 3000 of Outkast had the same reaction hearing the song as a young fan. "They were jamming so hard," he said.

Wu-Tang Clan, Ghostface Killah, Masta Killa, Raekwon, RZA, Ol' Dirty Bastard, GZA, U-God, Method Man

Wu-Tang Clan, ‘C.R.E.A.M.’

Enter the Wu-Tang (36 Chambers), 1993

Part of Wu-Tang‘s greatness was their messy, multitudinous sprawl, but the best song on their debut is ruthlessly efficient: just two breathless verses, plus the catchiest acronym in history, laying out the ground rules of street capitalism. RZA’s sampled pianos rattle like the wind down a project alleyway as Raekwon and Inspectah Deck trade harrowing war stories: “No question I would speed/For cracks and weed/The combination made my eyes bleed.”

Eric B, Rakim

Eric B. and Rakim, ‘Paid in Full’

Paid in Full, 1987

Exhibit A in the case for Rakim as hip-hop’s John Coltrane: His incandescent thought-bubble rap – barely a minute long – is all iced flow and sly beat-dodging, a good-vs.-evil meditation that calmly frames thug life inside real-life economics (an appetite for “a nice big plate of fish/Which is my favorite dish”) and a novelist’s eye for detail (“Ain’t nothin’ but sweat inside my hands”). The primordial beat, taken from the Soul Searchers’ “Ashley’s Roachclip,” inspired U.K. DJ team Coldcut to craft “Paid in Full (Seven Minutes of Madness)” – arguably the best remix in hip-hop.


N.W.A., MC Ren, Eazy E, Dr. Dre

N.W.A, ‘Straight Outta Compton’

Straight Outta Compton, 1988

“A murder rap to keep you dancin’ with a crime record like Charles Manson,” the explosive first track on N.W.A‘s 1988 debut combined multi-layered, amped-up, Public Enemy-style production with a raw menace like nothing anyone had heard before. It almost single-handedly shifted hip-hop’s focus from New York to South Central Los Angeles, despite MTV’s refusal to air the video for “Compton” because of its gun-happy imagery. “Kids were just waiting for it,” said Bryan Turner of Priority Records, which sold 2 million copies of the single. One of those kids was Chris Rock, who brought a copy from L.A. for his dumbfounded East Coast friends to hear: “[N.W.A were] bigger than Madonna or Nirvana,” he said. “It was kind of like the British Invasion for black people.”

Notorious BIG

Notorious B.I.G., ‘Juicy’

Ready to Die, 1994

The greatest rapper that ever lived at his absolute peak: hilarious, incisive and insanely inventive as he balances urban realism (“Birthdays were the worst days”) and playalistic excess (“Now we sip champagne when we’re thirsty”). The funky first single from the Notorious B.I.G.‘s world-smacking 1994 debut, Ready to Die, was a departure from the rugged East Coast rap sound he wanted. But executive producer Sean “Puffy” Combs insisted Big flow over a simple, club-friendly loop of Mtume’s early dance-party jam “Juicy Fruit.” (Producer Pete Rock says that Combs got the idea for the track from him.) “I wanted to release music that let people know he was more than just a gang­sta rapper,” Combs said later. “He showed his pain, but in the end he wanted to make people feel good.”

Public Enemy, Chuck D, Flavor Flav, Professor Griff, DJ Lord

Public Enemy, ‘Fight the Power’

Fear of a Black Planet, 1990

Public Enemy's co­-producer Hank Shocklee said the group wanted their track for Spike Lee's explosive movie Do the Right Thing to have a "defiant, aggressive, 'I'm not gonna take it' feeling." They nailed it: No band since the Sex Pistols had pushed pop music's sonic and political possibilities as far as Public Enemy did on "Fight the Power." Chuck D blasted "straight-up racist" institutions like Elvis, John Wayne and the U.S. Postal Service, and the Bomb Squad layered samples over samples (James Brown, the Dramatics, Bob Marley) into implosive war-dance funk. With a frenetic­ protest-rally-themed video shot by Lee in Bed-Stuy, Brooklyn, the song was the total in-your-face package. In the summer of 1989, it seemed like it might start a revolution.

Dr Dre, Snoop Dogg

Dr. Dre feat. Snoop Doggy Dogg, ‘Nuthin’ But a ‘G’ Thang’

The Chronic, 1992

Climbing to Number Two on the singles chart in early 1993, "Nuthin' But a 'G' Thang" made Dr. Dre the undisputed flag bearer of West Coast rap, while also ushering that genre into the pop mainstream. The song's secret weapon was a relatively unknown pup named Snoop Doggy Dogg, whose verses are packed with effortless quotables. The song also introduced Dre's masterful "G-Funk" style of production, which updated George Clinton's legacy with slow, rubbery funk and layered synth hooks. "We made records during the crack era, where everything was hyped up, sped up and zoned out," Chuck D explained. "Dre came with ' "G" Thang' and slowed the whole genre down. He took hip-hop from the crack era to the weed era."

Geto Boys, Willie D, Bushwick Bill, Scarface

Geto Boys, ‘Mind Playing Tricks on Me’

We Can’t Be Stopped, 1991

In 1991, Bushwick Bill of the Geto Boys took a bullet – reportedly self-inflicted – in the eye during a suicidal freakout. He survived; a photo of the diminutive MC displaying his wound appeared on the Texas trio’s album cover. This Top 30 hit – a classic of cracked ghetto armor that put Houston hip-hop on the map – revealed even more of the manic depression and death wish inside their rhymes. Scarface, who wrote and produced the track, sounded like his movie namesake: fully armed at the edge of sanity, over dark-treble guitar and a gunslinger-walk rhythm sampled from an old Isaac Hayes tune. “It was an awesome, complex display of paranoia,” says Questlove. “It managed to add a third dimension [to Geto Boys’ sound], and it humanized them.” 

Run DMC, Jam Master Jay

Run-DMC, ‘Sucker M.C.’s’

Run-D.M.C., 1983

In the beginning, hip-hop was club music, an offshoot of disco. After “Sucker M.C.’s,” it belonged to teenagers on the street. Nothing more than brawling rhymes over a spare beat from an Oberheim DMX drum machine, the song appeared as the B side to Run-DMC’s debut single, “It’s Like That,” and cut with sidewalk-­spinning break dancers in mind. “There was never a B-boy record made until we made ‘Sucker M.C.’s,'” said Run-DMC DJ Jam Master Jay. But the song’s lyrics were as potent as its whiplash groove. Run charts his creation myth (“Two years ago, a friend of mine/Asked me to say some MC rhymes”) before his partner introduces­ himself: “I’m DMC in the place to be/I go to St. John’s University!” flying his alma mater like gang colors. A new school had arrived. 

Afrika Bambaata soul sonic force

Afrika Bambaataa & the Soul Sonic Force, ‘Planet Rock’

Non-album single, 1982

“One of the most influential songs of everything,” says Rick Rubin. “It changed the world.” Helmed by 25-year-old Kevin “Afrika Bambaataa” Donovan, a reformed South Bronx gang-member-turned-punk-mystic-community-leader/DJ – with help from superstar producer-in-the-making Arthur Baker and keyboardist John Robie this atom bomb interpolated parts of Kraftwerk‘s “Trans-Europe Express” and “Numbers,” mating synth stabs with robotic MC chants (“Rock rock to the planet rock/Don’t stop!”) into a jam that got the world break-dancing. It introduced Roland 808 beats to hip-hop, for which acts from the Beasties to Kanye would be grateful. Even more important, it coined the sonic language of electro, Detroit techno, freestyle R&B, Miami bass, Brazilian favela funk – i.e., much of modern dance music. “At the time we barely considered it a rap record,” says Rubin. “It was more about this new sound.” Chuck D adds crunk music to the list of genres that “Rock” inspired: “It’s as important as Willie Mitchell or Booker T. were to the Memphis scene. There hasn’t been a song like it in hip-hop since.” 

sugarhill gang

Sugarhill Gang, ‘Rapper’s Delight’

Non-album single, 1979

It took three guys from New Jersey to put hip-hop, a still-underground New York club phenomenon, on Top 40 radio for the first time. Three years before “The Message,” Sylvia Robinson’s Sugar Hill Records was facing bankruptcy when she made a discovery in a Harlem club. “She saw a DJ talking and the crowd responding,” remembered her son Joey. “She said, ‘Joey, wouldn’t this be a great idea to make a rap record?'”

Robinson (who passed away in 2011) assembled the Sugarhill Gang – Joey discovered Henry “Big Bank Hank” Jackson working at a pizzeria, listening to an early hip-hop tape, and asked him if he knew how to rap. The original 12-inch single, “Rapper’s Delight,” was 15 minutes of undeniable urban-playboy bragging – some of it “borrowed” from Grandmaster Caz of the Cold Crush Brothers – over a rhythm track that blatantly quoted the bass line in Chic’s 1979 hit “Good Times.” Bassist Chip Shearin had to play that lick for a quarter-hour. “We were sweating bullets because that’s a long time,” he said. (Shearin, then 17, was paid $70. Chic’s Nile Rodgers and Bernard Edwards did much better, getting writer credits after legal action.)

“Rapper’s Delight” was edited down to six and a half minutes and reached Number 36 on the pop charts, and suddenly rap was a viable genre for recorded music. Bronx hip-hop pioneers like Grandmaster Flash were shocked: When he first heard it on the air, he asked, “The Sugarhill who? Who are these people?” 

grandmaster flash and the furious five

Grandmaster Flash and the Furious Five, ‘The Message’

The Message, 1982

“The Message” was a total knock out of the park,” says Chuck D. “It was the first dominant rap group with the most dominant MC saying something that meant something.” It was also the first song to tell, with hip-hop’s rhythmic and vocal force, the truth about modern inner-city life in America – you can hear its effect loud and clear on classic records by Jay-Z, Lil Wayne, N.W.A, the Notorious B.I.G. and even Rage Against the Machine. Over seven minutes, atop a creeping rhythm closer to a Seventies P-Funk jam, rapper Melle Mel and co-writer Duke Bootee, a member of the Sugar Hill Records house band, traded lines and scenes of struggle and decay: drugs, prostitution, prison and the grim promise of an early death. There was a warning at the end of each verse: “Don’t push me, ’cause I’m close to the edge/I’m trying not to lose my head,” each word enunciated like a gunshot.

Flash, born Joseph Saddler, grew up in a neighborhood that closely resembled the song: the South Bronx during the worst of the Seventies urban blight. He and the Furious Five had become the number-one DJ crew in the borough – pushing aside early pioneers like Kool Herc and Pete “DJ” Jones – with a mix of party-hearty showmanship and Flash’s groundbreaking turntable skills. (Among other things, he invented the scratch.)

In a 1983 interview, Flash claimed “The Message” showed that he and the Five “can speak things that have social significance and truth.” But when Flash and the Furious Five first heard Bootee’s original demo (a track the latter called “The Jungle”), they worried that hip-hop clubgoers would not dig the subject matter and slowed-down beat, unusual for an early rap record. As Melle Mel remembered, he was the group member who “caved in” and agreed to record it; Sugar Hill boss Sylvia Robinson got him to write and rap more lyrics to Bootee’s track, and Sugar Hill studio player Reggie Griffin added the indelible synthesizer lick. Despite the credit on the record, Flash and the rest of the Five appeared only in a closing skit, in which they’re harassed and arrested by police.

“The Message” was a commercial success, peaking at Number Four on Billboard‘s R&B-singles chart, but its messy birth was fatal to Flash and the Five, who split into factions. Their most notable reunion would finally come in 2007, when they became the first rap group inducted into the Rock and Roll Hall of Fame. 

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