100 Greatest Hip-Hop Songs of All Time - Rolling Stone
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100 Greatest Hip-Hop Songs of All Time

What makes a great hip-hop song?

100 Greatest Hip-Hop Songs of All Time

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We asked 33 artists and experts – from Rick Rubin to Big Boi, Mike D to Chuck D – to vote for their favorite hip-hop songs.

100 Greatest Hip-Hop Songs of All Time

Roxanne Shanté, “Roxanne’s Revenge”

The first and greatest “Roxanne” response record birthed a unique hip-hop voice. On “Roxanne’s Revenge,” 14-year-old Lolita Shanté Gooden teamed up with producer Marley Marl and fired back at rap machismo. “My name’s just startin’ to blow up a little bit – and someone’s shooting me down,” laughed U.T.F.O.’s the Kangol Kid. Shanté went on to record classics like “Have a Nice Day” and “Go On Girl,” becoming one of rap’s revolutionary female voices.

100 Greatest Hip-Hop Songs of All Time

U.T.F.O., “Roxanne, Roxanne”

Hip-hop’s first beef war started innocently enough. In 1984, Brooklyn trio U.T.F.O. released a lackluster single called “Hanging Out.” Its B side, however, caused a sensation: “Roxanne, Roxanne,” an irresistible jam where the peacocking guys in U.T.F.O. get repeatedly shot down by a “stuck-up” hottie. Soon the New York hip-hop market was overrun with jams like “Sparky’s Turn (Roxanne You’re Through)” and the unforgettable “Roxanne’s a Man (The Untold Story).”

100 Greatest Hip-Hop Songs of All Time

Too $hort, “Freaky Tales”

Bay Area O.G. Todd Anthony Shaw – a.k.a. Too $hort – exerted a massive influence on West Coast hip-hop with his laid-back flow and pimp rhymes. “Freaky Tales” was his finest hour, an incredible 10 minutes of lascivious versifying. “It’s like bar after bar after bar,” recalled Snoop Dogg. “And niggas remembered that shit and learned that shit.”

100 Greatest Hip-Hop Songs of All Time

Raekwon feat. Ghostface Killah, Method Man, Cappadonna, “Ice Cream”

Raekwon’s 1995 solo album was a tour de force of stark beats and densely woven crime narratives. But its best song is all lighthearted fun, a freewheeling riff on the image of “titties” as ice cream cones; Ghostface Killah, Cappadonna, Method Man and Raekwon get theirs over RZA’s sunnily creeping beat. “I came up with the idea to make T-shirts to go with it,” RZA said.

100 Greatest Hip-Hop Songs of All Time

Nas, “It Ain’t Hard to Tell”

Backed by Large Professor’s heart-in-your-throat collage of drums, horns and a coveted Michael Jackson sample, the lead single from Illmatic unveiled Nas’ raspy project poetics. “We took ‘Human Nature’ and … made it real scratchy and scruffy,” said Large Professor. “Everything he’s saying is uplifting … but it’s for the hood.”

100 Greatest Hip-Hop Songs of All Time

Naughty by Nature, “O.P.P.”

This classic cheating song was inspired by a pal from Naughty by Nature’s East Orange, New Jersey, neighborhood who used the phrase O.P.M. for “other people’s money.” “We decided to flip that to ‘O.P.P.,'” recalled Vin Rock. The group thought its subject matter was too raw for radio, but it became a pop-rap smash.

100 Greatest Hip-Hop Songs of All Time

Rammellzee and K-Rob, “Beat Bop”

“Beat Bop” was a one-off studio rendition of a hip, early-Eighties downtown-Manhattan dance party. Graffiti star-child Jean-Michel Basquiat bankrolled and produced the 10-minute track. In it, frisky 15-year-old rapper K-Rob and raconteur Rammellzee had a hypnotic MC battle over a dubby beat and a violin. It’s an iconic old-school head-trip.

100 Greatest Hip-Hop Songs of All Time

Ultramagnetic MC’s, “Ego Trippin'”

With a James Brown vocal bit flipped to make the Godfather of Soul sound like a Martian bobcat and bizarre rhymes from legendary head case Kool Keith (“Like a migraine headache, your cells start to melt/While the Technics spin, the wax is on the felt”), the Bronx crew built a radical early hip-hop jam. Said DJ Premier, “They was like the astronauts of hip-hop.”

100 Greatest Hip-Hop Songs of All Time

A Tribe Called Quest, “Can I Kick It?”

Deploying the bass line from Lou Reed’s “Walk on the Wild Side” and a sample from organist Lonnie Smith, “Can I Kick It?” was a high point for eclectic, buoyantly Afrocentric hip-hop. Q-Tip raps that Tribe “flows in layers.” Indeed they did. And a new artistic bar was being set.

100 Greatest Hip-Hop Songs of All Time

Slick Rick, “Children’s Story”

Slick Rick was hip-hop’s first great storyteller – “wise as an owl, soft as a dove” amid “all these angry motherfuckers,” as he put it. And this bedtime tale about two kids who take up “robbin’ old folks” remains hip-hop’s most deftly detailed story-song. Told in a flurry of voices, it rendered Rick’s “ghetto ambience” with playful brilliance.

100 Greatest Hip-Hop Songs of All Time

M.O.P., “Ante Up (Robbing-Hoodz Theory)”

Brooklyn’s mash-out posse jolted you like the potholes of their Brownsville streets. When they howled, “Yap that fool/Ante up!/Kidnap that fool!” you checked for an exit, even if you were chilling at home. With its relentless horns and larcenous lyrics, “Ante Up” was the ultimate New York street anthem.

100 Greatest Hip-Hop Songs of All Time

Gang Starr, “Mass Appeal”

DJ Premier grabbed the scratched hook (“Money’s growin’ like grass with the mass appeal”) from “Pass Da Mic” by Philly also-rans Da Youngsta’s and the melody loop from fusion jazzbo Vic Juris to create the ultimate indictment of pandering pop-rappers. Guru, who died in 2010, rocks a gruff tough-love flow that made him one of the most honored voices in hip-hop.

100 Greatest Hip-Hop Songs of All Time

Outkast, “Ms. Jackson”

Based around a reconfigured bit of the Seventies soul hit “Strawberry Letter 23,” this is the rarest kind of hip-hop song: a heartfelt apology, inspired by André 3000’s worries and guilt over his relationship issues with Erykah Badu. “Music gives you the chance to say what you want to say,” André said. “And her mom loved it. She’s like, ‘Where’s my publishing check?'”

100 Greatest Hip-Hop Songs of All Time

Wu-Tang Clan, “Protect Ya Neck”

On their 1992 debut single, all nine Wu-Tang rappers unleash a dizzying flurry of styles, punch lines and nicknames, jerked forward by the defiantly bleary beats of the RZA, who got $100 from each MC for funding. “That’s the introduction of our careers right there,” says Raekwon. “That record definitely made the biggest statement for us.”

100 Greatest Hip-Hop Songs of All Time

Jay Z and Kanye West, “Ni**as in Paris”

“Don’t let me get in my zone,” West raps. Too late. Recorded at the Le Meurice hotel in Paris, this minimalist thunderbolt embodied Ye’s claim that his music was “where art meets commercial.” But the song is no breezy high-life jam: West barks about wilding out in France, while Jay imagines the dark fate that could have awaited him had he not become Jay Z.

100 Greatest Hip-Hop Songs of All Time

Ol’ Dirty Bastard, “Brooklyn Zoo”

“If Dirty wasn’t rhyming in the booth, he was talking or goofing around, and he wanted us to record all of it,” said his hype man Buddha Monk. That madcap genius is all over “Brooklyn Zoo,” which was co-produced by ODB, especially on its endlessly repeated chorus. “It’s like Screamin’ Jay Hawkins somehow made the best hip-hop single in history,” recalled Questlove.

100 Greatest Hip-Hop Songs of All Time

Kanye West feat. Jay Z, Rick Ross, Bon Iver, Nicki Minaj, “Monster”

Kanye West was on an opulent creative splurge when he recorded this tornadic posse cut featuring Rick Ross, Jay Z and indie-folk wisp Bon Iver. But the breakout star was Nicki Minaj, promising to eat our brains with her gold-teeth fangs and stealing the song’s psycho-horror video. Said Ross, “I knew then she’s one of the greatest.”

100 Greatest Hip-Hop Songs of All Time

Dead Prez, “Hip-Hop”

The most succinct mission statement for Afrocentric anti-corporate, revolution-minded hip-hop since Public Enemy. These Brooklyn radicals invaded radio playlists, demanding a choice between “a Lexus or justice.” Said rapper M-1, “It was an attempt to get to the level of sickness within our people.”

100 Greatest Hip-Hop Songs of All Time

T.I., “What You Know”

Atlanta rapper T.I. hit the Top 10 with this epic, a standout pop moment for Southern trap music. Producer DJ Toomp and co-producer Wonder Arillo came up with the colossal, heart-tugging synths – which were an homage to Roberta Flack’s 1970 cover of the Impressions’ “Gone Away.” “When T.I. heard it,” Toomp said, “he had the hook in, like, 10 minutes.”

100 Greatest Hip-Hop Songs of All Time

Ice T, “6 ‘n the Mornin'”

Ice T culled from his real-life experience to write the pioneering gangsta rhyme, detailing a first-person picaresque of a “self-made monster of the city streets” over a stark electro-thwack. “It’s like if you made eggs every mornin’ and one day someone said, ‘Hey, you should sell these eggs,'” Ice T recalled. “To me, my life was so involved in that drama every day, it was easy.”

100 Greatest Hip-Hop Songs of All Time

Lil Wayne, “A Milli”

Released as the New Orleans pun-machine was being hailed “the greatest rapper alive,” Lil Wayne’s biggest hit saw him compare himself to B.I.G., 2Pac and Jay Z over a spacey minimalist beat. Producer Bangladesh confirmed Wayne’s boast that he never wrote down hit rhymes: “He went in on it immediately, just freestyle.”

100 Greatest Hip-Hop Songs of All Time

Sir Mix-A-Lot, “Baby Got Back”

“[At the time] you had these Spuds MacKenzie girls, little skinny chicks looking like stop signs, with big hair and skinny bodies,” recalled Sir Mix-A-Lot. “I did it as a knee-jerk response to that kind of stuff.” The Seattle rapper-producer’s slinky electro beat and hilarious video made for pop’s greatest positive-body-image jam.

100 Greatest Hip-Hop Songs of All Time

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

Riding a sample of jazz bassist Ron Carter, the New York duo of Dres and Mista Lawnge rocked the nursery-rap chant, “Engine engine No. 9 on the New York transit line,” to give Native Tongues hip-hop a jubilant mosh-pit energy. The song still sucks you in with electromagnetic force.

100 Greatest Hip-Hop Songs of All Time

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

Some of the lyrics to this menacing track were originally part of a demo called “Trigger Happy Nigga,” which got the L.A. crew its record deal. Vocalist B-Real spit his roughneck verses over DJ Muggs’ beat (which featured a Farfisa from garage-rock footnotes the Music Machine), and a blunted masterpiece was born.

100 Greatest Hip-Hop Songs of All Time

Dr. Dre feat. Snoop Doggy Dogg, “Deep Cover”

The world’s introduction to Snoop Doggy Dogg – before the gin, juice, pimps or ho’s. For his recorded debut, on Dr. Dre’s first post-N.W.A solo effort, the lean scrapper took this song (which had been originally slated for The Chronic) and made it the template for his style. (It’s definitely more memorable than Deep Cover, the movie it came attached to.) Over a dissonant piano clank and Dre’s bass-drum kaboom, Snoop played the steely black youth at war with the LAPD, delivering the chorus – “‘Cause it’s 1-8-7 on an undercover cop” – with a singsong smirk. Asked about using police code for murdering an officer as a hook, Snoop said, “If [the press] would have went in-depth on that song, there would have been some shit out of that.”

100 Greatest Hip-Hop Songs of All Time

Beastie Boys, “Hold It, Now Hit It”

Before the Beasties dominated MTV, they launched a sneak attack on black radio with this hard-hitting, White Castle-referencing jam. “The fact that they were white definitely made them stand out,” said Def Jam’s Russell Simmons. “But they were ultimately accepted by black people because they were good.”

100 Greatest Hip-Hop Songs of All Time

Doug E. Fresh and the Get Fresh Crew, “The Show”

A record that’s like a variety revue on wax. Fresh’s giddy human beatboxing and Slick Rick’s sly flair made “The Show,” which was backed with the equally classic “La-Di-Da-Di,” a global hit. “I was 17, and I’d made a million dollars,” Fresh recalled. “It was huge.”

100 Greatest Hip-Hop Songs of All Time

Eminem feat. Dido, “Stan”

Eminem’s scariest song because, for once, the horror seemed real. Anchored by a sample of U.K. singer Dido’s “Thank You” (which also became a hit), the song followed an obsessed fan who acts out Em’s deranged fantasies. “I try to help him at the end of the song,” Em said. “It kinda shows the real side of me.”

100 Greatest Hip-Hop Songs of All Time

The Pharcyde, “Passin’ Me By”

Hooking up in a South Central music workshop, the Pharcyde brought fresh artistry and exuberance to hip-hop. Over a track that bopped like the Bomb Squad on a beach getaway, four distinct rappers complemented each other with quippy charm – to member SlimKid3, this song was like “a beautiful bird circling our heads all day.”

100 Greatest Hip-Hop Songs of All Time

Clipse, “Grindin”

Hitmaking production duo the Neptunes (featuring Pharrell Williams) cooked up a chilling electro-funk beat for their Virginia homies the Clipse, and the result was a coke-rap classic: “From ghetto to ghetto/To backyard to yard/I sell it whipped, unwhipped/And soft, to hard,” Pusha T rapped. Come and get it.

100 Greatest Hip-Hop Songs of All Time

Grandmaster and Melle Mel, “White Lines (Don’t Don’t Do It)”

The funkiest anti-drug record ever, Melle Mel’s opening salvo after splitting with Grandmaster Flash and the Furious Five was also, alongside Blondie’s “Rapture,” one of the first rap/New Wave hybrids. Like the song says, it’s something like a phenomenon.

100 Greatest Hip-Hop Songs of All Time

Snoop Doggy Dogg, “Gin and Juice”

Enshrining the line “with my mind on my money and my money on my mind” as a hip-hop tenet, “Gin and Juice” was Cali G-funk’s laidback victory lap. “Little white kids come up to me, and it makes me feel damn good,” Snoop told Rolling Stone in 1993. “It’s the feeling of a straight ghetto man finally proving his stuff to the whole society.”

100 Greatest Hip-Hop Songs of All Time

Run-DMC, “King of Rock”

“I’m the king of rock, there is none higher/Sucker MCs should call me Sire,” barks DMC on this hugely influential rap-rock anthem, before guitarist Eddie Martinez drops detonating riffs. “King of Rock” came with a hilarious video where Run-DMC bum-rush a “rock & roll museum.” In 2009, they were inducted into the Rock and Roll Hall of Fame.

100 Greatest Hip-Hop Songs of All Time

The Notorious B.I.G., “Big Poppa”

With its plush, slow-jam feel and ghetto-fabulous video, Biggie’s first Top 10 hit sold America on a burly Brooklyn corner kid. Said co-producer Chucky Thompson, “Ice Cube was big at that time as well, and if you look at [Cube’s] ‘It Was a Good Day,’ and then you look at ‘Big Poppa,’ it was on the same wavelength.”

100 Greatest Hip-Hop Songs of All Time

Public Enemy, “Bring the Noise”

“Bring the Noise” was truth in advertising – from Chuck D’s megaphone-blast delivery to Terminator X’s teeming turntable scratches to the Bomb Squad horn, siren, snare-and kick-drum samples to Flavor Flav’s cartoonish absurdism (“We can do this, like Brutus”). Chuck D noted the urgency of the song’s 1987 recording: “Eric B. and Rakim and Boogie Down Productions … fucking changed the world, man,” he said. That meant “Bring the Noise” had to be “faster, funkier and also saying something serious that the people could feel.”

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