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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

Outkast, “B.O.B.”

Outkast greeted the 21st century with a single that’ll probably sound ahead of its time in the 22nd. Big Boi and André 3000 were inspired by hearing the hard, double-time rhythms of drum-and-bass music at a London party. “There wasn’t anything in hip-hop that was killing me at the time,” André said. “But that shit was tough … I thought about how to Americanize it.” With an insane beat, Hendrix-at-Monterey guitar and massed voices chanting like a gospel choir conducted by Afrika Bambaataa, “B.O.B.” became one of the greatest left-field hits of all time.

100 Greatest Hip-Hop Songs of All Time

Grandmaster Flash and the Furious Five, “The Adventures of Grandmaster Flash on the Wheels of Steel”

“I was just one big human sampler,” Joseph “Grandmaster Flash” Saddler once said of his groundbreaking record-mixing technique. And the Grandmaster never cut faster than on the record that established the hip-hop DJ as a new kind of pop musician. Flash’s days as a DJ date back to 1974, when he and other kids who were too young to get into discos began playing at house parties and block parties in their South Bronx neighborhoods. He was also an electronics geek who eventually came up with his own unique setup: using three turntables, a crossfader (a device he helped pioneer) and his own grab bag of frenetic moves. On “The Adventures of Grandmaster Flash on the Wheels of Steel,” 23-year-old Flash created a continuous party jam by splicing, scratching and, in a sense, reinventing records – “the short, climactic parts that really grabbed me,” he recalled. Chic, Blondie and Queen all make appearances in the mix, and Flash even threw in early rap hits by Spoonie Gee and his own crew, the Furious Five. Self-promotion never sounded so smooth.

100 Greatest Hip-Hop Songs of All Time

Marley Marl feat. Master Ace, Craig G., Kool G. Rap, Big Daddy Kane, “The Symphony”

Marley Marl was hip-hop’s first superproducer, a master of the chopped-and-looped soul sample and a huge influence on sound painters from RZA to Dr. Dre. On “The Symphony,” he dialed up a beat for the ages – a ferocious drum break and a snatch of Otis Redding piano – and summoned the cream of his Juice Crew affiliates. The result: a truly great late-Eighties posse cut. Smoothest flow: Big Daddy Kane. 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.

100 Greatest Hip-Hop Songs of All Time

Funky 4 + 1, “That’s the Joint”

“That’s the joint” captures the essence and energy of hip-hop’s party-hearty early glory days: nearly 10 minutes of exhortations and boasts, sprawling across a hopped-up disco beat. By today’s standards, the braggadocio is quaint – “We got rhymes on our minds, we got rockin’ in our heart” – but the rappers can flow, and the bass breakdown, by four-string god Doug Wimbish, is as funky as anything this side of Bootsy Collins. The real star of the show, though, is the Funky 4’s “plus-one woman,” Sha-Rock (a.k.a. Sharon Green), the first female MC featured on a hit rap record.

100 Greatest Hip-Hop Songs of All Time

Salt-N-Pepa, “Push It”

Salt-N-Pepa’s signature jam was one of the first rap records to top the dance charts, and it remains a classic party-starter. The electro groove is a monster, and the refrain distills the message of half the songs ever written in nine indelible words: “Push it! Push it good! Push it real good!” Cheryl “Salt” James and Sandra “Pepa” Denton weren’t technical virtuosos, but they trounce all comers. “Back then, there weren’t many women,” Pepa recalled. “We were raw, we were bold, we were in your face with it. We did not care!”

100 Greatest Hip-Hop Songs of All Time

Lauryn Hill, “Lost Ones”

The opening track on Lauryn Hill’s landmark solo debut 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. “It’s funny how money changes situations,” she begins, but what follows isn’t funny: a spit-roasting indictment of arrogance, greed and spiritual blindness. The song’s alleged target – Hill’s former bandmate in the Fugees and ex-lover Wyclef Jean – must have been quaking in his Timbs.

100 Greatest Hip-Hop Songs of All Time

De La Soul, “Me Myself and I”

Urged by their label to provide their adventurous 1989 debut album, 3 Feet High and Rising, with a song that wouldn’t be “so over someone’s head,” De La Soul concocted a cosmically inclusive house-party jam. Their eclectic Daisy Age style got them labeled hip-hop hippies, but it elevated a whole movement of Native Tongues groups like A Tribe Called Quest and the Jungle Brothers: “We are going back to the Sixties,” Posdnuos said in 1989. “But also to the Seventies, the Fifties, the Eighties and on into the future.”

100 Greatest Hip-Hop Songs of All Time

Audio Two, “Top Billin'”

Rhyming over nothing but the drum break from the Honey Drippers’ “Impeach the President” (brilliantly flipped by co-producer Daddy-O), Kirk “MC Milk Dee” Robinson thanks his parents, brags about his bodyguard and shouts-out both his Bed-Stuy hood and his DJ brother/partner Giz. He also invites rappers to “Bite a rhyme/If you dare.” Plenty did: Variations on the hook – “Milk is chillin’, Gizmo’s chillin’/What more can I say? Top billin’!” – have been spit by gazillions of MCs, from Dre to Biggie to Jay Z.

100 Greatest Hip-Hop Songs of All Time

Boogie Down Productions, “South Bronx”

Kris “KRS-One” Parker of Boogie Down Productions was rap’s original righteous teacher, and this funky-fresh story of hip-hop’s early days is a required master class. DJ Scott La Rock threads a no-nonsense James Brown sample, and KRS recalls a late-Seventies golden age of jams in the park and innovators like Afrika Bambaataa and Kool Herc. Sadly, the same year “South Bronx” was released, La Rock (born Scott Monroe Sterling) was shot while trying to break up a fight, ending one of Eighties hip-hop’s most promising careers.

100 Greatest Hip-Hop Songs of All Time

2Pac feat. Dr. Dre and Roger Troutman, “California Love”

On his biggest hit, 2Pac celebrated his recent 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 vocoder vocals from the legendary Roger Troutman. “The whole city was in pandemonium,” recalled Kendrick Lamar, who was perched on his father’s shoulders while he watched Dre and Pac shoot the song’s video. “I think since that day I was inspired, subconsciously, to be an artist.”

100 Greatest Hip-Hop Songs of All Time

Kurtis Blow, “The Breaks”

The first rap hit on a major label, peaking at Number 87 on Billboard’s Hot 100, 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,” introducing America to B-boy culture – “something I’m sure few people outside New York have ever seen,” he said in 1981 – while blazing a trail for rappers like Run of Run-DMC, who started out calling himself “The Son of Kurtis Blow.”

100 Greatest Hip-Hop Songs of All Time

Eminem, “My Name Is”

“God sent me to piss the world off,” announced Eminem – and by the time the curtain dropped on his debut single, he’d fulfilled his mission. It was a sound no one had heard before: a white rapper from a Midwestern trailer park with a seemingly bottomless supply of uproarious rhymes. Over Dr. Dre’s cartoon-funk beat, Em tears off Pamela Anderson’s breasts, goes after his junior high English teacher’s testicles with a stapler and rhymes “head straight” and “impregnate.” “If you’re sick enough to think it,” he said at the time, “then you’re sick enough to say it.”

100 Greatest Hip-Hop Songs of All Time

Missy Elliott, “Get Ur Freak On”

“Me and Timbaland been hot since 20 years ago,” crows Elliott, a ludicrous boast that seemed almost plausible in the late Nineties and early Aughts, when the pair were music’s most reliable brainbenders. “Get Ur Freak On” is Missy and Tim at their funkiest and nuttiest. The production takes hip-hop Orientalism to outer space, marshaling Indian tablas and snatches of Japanese speech. “When it blew like that, I realized there was a whole other part of the world that people were ready for,” she said. “It was a good thing.”

100 Greatest Hip-Hop Songs of All Time

Outkast, “Rosa Parks”

The song that made the world fall in love with Outkast brought earthy Southern flavor to the rap charts. Big Boi and André 3000’s party rhymes were deceptively deep, and their flow was smoother than Georgia molasses. As for Rosa Parks: She felt the lyrics made light of her heroism and brought a lawsuit against the group. “We never intended the song to be about Rosa Parks,” André told Rolling Stone at the time. “It was just symbolic, meaning that we were comin’ back out, so all you other MCs move to the back of the bus.”

100 Greatest Hip-Hop Songs of All Time

Ice Cube, “It Was a Good Day”

Ice Cube’s biggest hit is a ghetto pastorale, forsaking violence to revel in good vibes and a plush Isley Brothers sample. “I rap all this gangsta stuff,” he later said. “What about all the good days I had?” Cube eats a fine breakfast, smokes his homeys on the basketball court and smokes some chronic with a girl. He even looks up to see “the lights of the Goodyear blimp/And it read, ‘Ice Cube’s a pimp.'” Recently, the Internet went nuts trying to nail down the actual date of Cube’s good day – but it’s obviously a fairy tale, with its own happily-ever-after ending. As Cube said himself, “It’s a fictional song.”

100 Greatest Hip-Hop Songs of All Time

Mobb Deep, “Shook Ones (Part II)”

In the mid-Nineties, Mobb Deep came out of New York’s Queensbridge projects and boiled East Coast gangsta rap down to its rawest, nihilist essence. A suspense-amping snippet from a Quincy Jones soundtrack infuses the rumbling song with a sinister hiss, while background mumbles add shady menace. Prodigy, whose mother was a member of Sixties girl group the Crystals, promises that his “gunshots will make you levitate,” and makes sure to remind listeners that he’s “only 19.” Years later, you still ache for that kid.

100 Greatest Hip-Hop Songs of All Time

Schoolly D, “P.S.K. What Does It Mean?”

“This birthed gangsta rap,” Questlove said. “N.W.A just took this formula and ran with it.” The Philly rapper’s 1985 joint takes its name from a local gang, Park Side Killers, and its wicked “Sucker MCs”-style beats from an evidently stressed-out Roland 909 drum machine. In a lazily menacing flow, Schoolly buys coke, parties with a hooker, buys weed and goes to the club, where he finds an MC biting his style. “Put my pistol up against his head,” he matter-of-factly explains. That he decides not to pull the trigger makes the jam no less chilling.

100 Greatest Hip-Hop Songs of All Time

Jay Z, “99 Problems”

Rick Rubin hadn’t worked on a hip-hop project for years when Def Jam’s Lyor Cohen persuaded him to get in the studio with Jay Z. “I knew I was gonna get fresh shit,” Cohen recalled. He got one of the most explosive tracks ever, based around the gigantic drums from Billy Squier’s “The Big Beat.” Jay concocts an indelible pop chorus and sketches out a scene based on an encounter with a racist cop from his pre-stardom days. “The first offense wasn’t the crack in the ride but the color of the driver,” he wrote in his memoir.