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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

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.

100 Greatest Hip-Hop Songs of All Time

Kanye West, “Jesus Walks”

Kanye West has never been shy about his God complex, but humility, not hubris, drives hip-hop’s greatest gospel testimonial. The production is stirring – a church choir cresting above a martial beat – and West has a message to match, forsaking easy pieties to rap about internal struggle (“We at war with ourselves”) and self-doubt (“I want to talk to God, but I’m afraid because we ain’t spoke in so long”). The song helped solidify his own transcendent status: “I made ‘Jesus Walks,'” West rapped years later on “Otis.” “I’m never going to hell.”

100 Greatest Hip-Hop Songs of All Time

Nas, “N.Y. State of Mind”

No track better sums up Nas’ ability to spin dense, dazzlingly lucid verses. “N.Y. State of Mind,” a highlight of his hugely important 1994 debut, Illmatic, 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 was later broken up to create a spellbinding track. “He did the whole first verse in one take,” recalled producer DJ Premier, who exactingly balanced two jazz samples for the muted, moonlit beat. “He stopped and said, ‘Does that sound cool?’ And we were all like, ‘Oh, my God!'”

100 Greatest Hip-Hop Songs of All Time

The Notorious B.I.G., “Hypnotize”

Notorious B.I.G’s first Hot 100 chart-topper, which hit Number One just weeks after his March 1997 murder, is his supreme pop-rap moment: a litany of boasts and threats, delivered with cool sangfroid over Puff Daddy’s Herb Alpert-sampling candy-corn beat. It was a fitting epitaph, a testament to Biggie’s inimitable flow, matchless wordplay and knack for leavening gangsta sex and violence with punch lines even a toddler could cuddle up to. “Such a likable guy,” said Jay Z. “He’s forever loved by hip-hop.”

100 Greatest Hip-Hop Songs of All Time

LL Cool J, “Mama Said Knock You Out”

“Don’t call it a comeback!” begins rap’s hottest-ever comeback. After finding crossover success in the late Eighties, LL Cool J returned to street-fighting hip-hop – pledging to “bash this beat like a skull” and returning fire from Kool Moe Dee’s diss record “How Ya Like Me Now?” The beat, one of legendary producer Marley Marl’s finest tracks, rides the four-count chant from Sly and the Family Stone’s “Trip to Your Heart,” and the track peaks with LL repeating “Damage! Damage! Damage!” like he’s done rhyming and is ready to break shit. Point made.

100 Greatest Hip-Hop Songs of All Time

Eminem, “Lose Yourself”

Eminem’s biggest hit ever 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 writing autobiographically, sidestepping demented hijinks 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,” said engineer Steven King. “Jaws dropped – we were like, ‘Oh, my God! This story has been building in him.'”

100 Greatest Hip-Hop Songs of All Time

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

Craig Mack has faded into obscurity – reportedly renouncing rap to join a fundamentalist Christian cult in South Carolina – but he left his mark with the remix of his debut single. Mack’s verse has its moments – “I wanna grab my dick/Too lazy/Hold it for me” – but labelmate Biggie Smalls drops a true classic, opening his freestyle with “Niggas is mad I get more butt than ashtrays.”

100 Greatest Hip-Hop Songs of All Time

A Tribe Called Quest feat. Leaders of the New School, “Scenario”

Q-Tip, Phife Dawg and Ali Shaheed Muhammad made their reputation as jazz-influenced bohemian innovators, but their best song is a full-on B-boy shout-along. For many hip-hop heads, this summit meeting between A Tribe Called Quest and Leaders of the New School is hip-hop’s greatest posse cut. The breakout performance comes from 19-year-old upstart Busta Rhymes, who emerges roaring like a dungeon dragon. “I thought he was it,” Q-Tip said later. “I just wanted to set him up.”

100 Greatest Hip-Hop Songs of All Time

Big Daddy Kane, “Ain’t No Half-Steppin'”

When Jay Z christened Brooklyn’s Barclays Center with an eight-show run, he only brought out one guest: Big Daddy Kane. And for good reason: Antonio Hardy was the killer wordsmith of hip-hop’s golden age. On “Ain’t No Half-Steppin’,” his tone is rich and commanding as he rocks tightly coiled, extended metaphors over Marley Marl’s laidback groove: “Rappers, you better be/Ready to die because you’re petty/You’re just a butter knife, I’m a machete.” Legend has it even Rakim turned down a challenge to go mic-to-mic with Kane.

100 Greatest Hip-Hop Songs of All Time

Rob Base and DJ E-Z Rock, “It Takes Two”

“All I know is, it’s a club banger,” Rob Base said. Mixing hip-hop and dance music, lifting liberally from James Brown background singer Lyn Collins’ 1972 song “Think (About It),” Base and DJ E-Z Rock’s irresistible 1988 smash was a pop-rap landmark and an ode to understanding and respect that brought people together under a groove. 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.'”

100 Greatest Hip-Hop Songs of All Time

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

“When I’m writing I’m trapped between the lines/I escape when I finish the rhyme,” explains Rakim, rocking the sort of jam that disappeared once copyright lawyers stepped up their game. Eric B. built this landmark 1987 track by looping a chunk of the James Brown-produced song of the same name (recorded in 1970 by Bobby Byrd and the J.B.’s). But turnabout is fair play: British mixmasters M/A/R/R/S built their hit “Pump Up the Volume” around a sample of Rakim saying that phrase on “I Know You Got Soul.”

100 Greatest Hip-Hop Songs of All Time

EPMD, “Strictly Business”

The best 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 wildstyle moves on the floor next to Mountain and Kool and the Gang. Erick Sermon and Parrish Smith’s laid-back rhymes were revolutionary, too. Most rappers in 1988 were still stuck on the brash cadences that town criers from LL Cool J to Chuck D favored; EPMD’s casual, goofy approach to the mic laid the groundwork for generations of chilled-out MCs.

100 Greatest Hip-Hop Songs of All Time

LL Cool J, “Rock the Bells”

Leaping off a hard-rock riff from AC/DC’s “Flick of 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.” The third single from his 1985 debut is Rick Rubin’s remix of an early 12-inch version that, in fact, had bells. But this one rings even louder. It’s a rap Rosetta Stone quoted to this day. LL liked it so much he sampled it himself on 1991’s equally crushing “Mama Said Knock You Out.”

100 Greatest Hip-Hop Songs of All Time

50 Cent, “In Da Club”

“We just made some shit we wanted to hear,” producer Dr. Dre said. “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 talented thug who’d once taken nine bullets), the backing of Dr. Dre and Eminem and a lush, languid flow. All he needed was a monster beat; over clinically precise handclaps and synths, he sent America 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.

100 Greatest Hip-Hop Songs of All Time

Beastie Boys, “Paul Revere”

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.” 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 on records and Yauch turned to Buddhism. But they performed “Paul Revere” right to the end: at Bonnaroo in 2009, Yauch’s last show before his death in 2012.

100 Greatest Hip-Hop Songs of All Time

2Pac, “Dear Mama”

“The emotional, the sad songs, were his personal favorite,” recalled 2Pac producer Johnny J. His 1995 ballad tribute to his mother, Afeni Shakur, is the ne plus ultra of hip-hop mom songs. Tony Pizarro’s beat sets a tender mood, and 2Pac strikes 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 realism, especially when Pac raps about his mother’s struggles with drug addiction: “And even as a crack fiend, Mama/You always was a black queen, Mama.”

100 Greatest Hip-Hop Songs of All Time

Run-DMC, “Peter Piper”

The greatest ode ever to the Midas-like powers of a DJ. Jam Master Jay sliced up composer Bob James’ 1975 smooth-jazz nugget “Take Me to the Mardi Gras” as Run and DMC dropped nursery-rhyme science in summing up their partner’s greatness: “He’s a big bad wolf in your neighborhood/Not bad meaning bad but bad meaning good!” Run-DMC’s label, Profile Records, wanted the MTV-ready rap-rock Aerosmith collaboration “Walk This Way” to be the first single off their 1986 album, Raising Hell. But the group was adamant that “My Adidas/Peter Piper,” anthems of hip-hop culture, be the first release; Darryl “DMC” McDaniels later recalled saying, “If ya’ll 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. When Jam Master Jay (born Jason William Mizell) was shot and killed in 2002, Run-DMC immediately retired. They’d eventually reunite again in 2012, with Jam Master Jay’s two sons as part of the group.

100 Greatest Hip-Hop Songs of All Time

Jay Z feat. UGK, “Big Pimpin'”

Jay Z has since claimed that 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,” he boasts. “What kind of animal would say this sort of thing?” Jay said of his own lyrics. “Reading it is really harsh.” But “Big Pimpin'” is the ultimate playa anthem, radiating excess and power. Jay defied North-South regional bias by reaching across the Mason-Dixon to give Port Arthur, Texas, duo UGK a prominent spot on one of his biggest hits. His guests’ nimble wordplay added a brilliant twist to the track: “Go read a book, you illiterate son of a bitch, and step up your vocab,” taunted Bun B. Timbaland’s beat fit the ecumenical vibe perfectly – a bugged-out orchestral sample lifted from a 1957 song by Egyptian singer Abdel Halim Hafez that gave Jay Z’s supersize boasts a perfect sense of world-straddling dominance.

100 Greatest Hip-Hop Songs of All Time

N.W.A, “Fuck tha Police”

The pivot point between Public Enemy’s Black Panther revivalism and gangsta rap’s nihilism, this 1988 hard-funk assault indicted the LAPD and seemed like prophecy in the Rodney King/L.A. riots era. “Fuckin with me cuz I’m a teenager/With a little bit of gold and a pager,” rhymes a 19-year-old Ice Cube, 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 the group’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 bad boys and made the song an agit-pop anthem for the ages. “Peace is a fiction to me,” Ice Cube told Rolling Stone in 1989. “We deal with reality. Violence is reality. When you say something like that, it scares people. You’re supposed to picture life as a bowl of cherries. But it’s not.”

100 Greatest Hip-Hop Songs of All Time

Public Enemy, “Rebel Without a Pause”

Opening with a Jesse Jackson sample (“Brothers and sisters, I don’t know what this world is coming to!”) and upping the ante with Chuck D’s broadcaster-baiting (“Radio/Suckers never play me”), this 1987 single perfected Public Enemy’s hand-grenade attack and set the stage for their seminal It Takes a Nation of Millions to Hold Us Back. Its siren squeal is actually a looped horn from the 1970 J.B.’s jam “The Grunt Pt. 1”; the groove bites James Brown’s “Funky Drummer”; and Terminator X scratches the chorus of Chubb Rock’s “Rock and Roll Dude.” (“We use samples like an artist would use paint,” said producer Hank Shocklee.) When Chuck D heard the finished recording, he was so blown away he announced, “I could die tomorrow.”

100 Greatest Hip-Hop Songs of All Time

Doug E. Fresh and Slick Rick, “La-Di-Da-Di”

Eye-patched British-American rapper Slick Rick was still known as MC Ricky D when “La Di Da Di” was released in 1985. Rick spins a rude 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 (name-checking Gucci, Bally, Kangol, Polo, Johnson’s Baby Powder and Oil of Olay), it would be referenced endlessly – most famously in the chorus of Notorious B.I.G.’s “Hypnotize.” It also started the trend of rappers breaking into off-key song. “La-Di-Da-Di” began as a live routine that turned into a sensation. “Doug E. used to carry me around with him,” Rick recalled. “The crowd … first they would look at you like, ‘Whatever, skinny nerd trying to get put on,’ but then when you kicked the humor and they got to laughing and enjoying themselves, it sold itself.”

100 Greatest Hip-Hop Songs of All Time

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

Hip-hop has produced many classic elegies – from Ice Cube’s “Dead Homiez” to Bone Thugs-N-Harmony’s “Tha Crossroads.” Pete Rock and C.L. Smooth’s “They Reminisce Over You” is as beautiful as they come. The early-Nineties duo wrote the song for their Mount Vernon, New York, pal “Trouble” T-Roy, a dancer with Heavy D and the Boyz who died while on tour in 1990. C.L. Smooth came up with his lyrics before Pete Rock had produced the track, which is hard to imagine since they fit together so perfectly. Over a tender, sky-blown sax sample from Sixties jazz-pop composer Tom Scott, C.L. Smooth spins a tribute to his fallen friend into a vivid celebration of family (literal, metaphorical and musical) that’s as much free-roaming backyard-barbecue toast as somber funeral speech. “When we listened back to the record, we just started crying,” Pete Rock recalled. “When I felt like that, I was like, ‘This is it.’ Deep in my heart I felt like this was gonna be something big.”

100 Greatest Hip-Hop Songs of All Time

Wu-Tang Clan, “C.R.E.A.M.”

Part of what made the Wu-Tang Clan so great was their messy, multitudinous sprawl. “When we started recording Enter the Wu-Tang, the whole group was usually there for every session; sometimes it felt like their whole neighborhood was in the studio,” recalled Ethan Ryman, an engineer on the group’s landmark 1993 debut. “Every now and then, RZA and I would have to clear the room so we could get to the equipment.” Yet the finest song on the album is ruthlessly efficient: just two breathless verses, plus the catchiest acronym-based hook in history, laying out the 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”). It’s not a romantic portrait, but it does have a happy ending, when Rae joins the Clan: “Figured out I went the wrong route/So I got with a sick-ass clique and went all-out.”

100 Greatest Hip-Hop Songs of All Time

Eric B. and Rakim, “Paid in Full”

Exhibit A in the case for Rakim as hip-hop’s John Coltrane. His incandescent thought-bubble rap on “Paid in Full” is all iced flow and sly beat-dodging, a good-versus-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 hand”). In an era when most hip-hop songs exploded with loud, over-the-top boasting, Rakim’s relatable, low-key flow was game-changing. “I always wanted to kind of make the listener feel like it was them that I was talking about, or to the point that I could say the rhyme and feel like it’s them saying it,” he said years later. Eric B.’s beat, looped from a break on “Ashley’s Roachclip” by the Soul Searchers, is just as groundbreaking; it inspired the British DJ team Coldcut to craft “Paid in Full (Seven Minutes of Madness),” which soon became the song’s definitive version, and arguably the dopest remix in hip-hop history.

100 Greatest Hip-Hop Songs of All Time

N.W.A, “Straight Outta Compton”

“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 kicked off the gangsta-rap era with a raw menace like nothing anyone had heard before. Ice Cube, Dr. Dre, MC Ren, DJ Yella and Eazy-E shifted rap’s focus from New York to South Central Los Angeles despite MTV’s refusal to air the video for “Compton” due to its violent imagery. “Kids were just waiting for it,” said Bryan Turner of Priority Records, which quickly sold 2 million copies of Straight Outta Compton. One of those kids was a young Chris Rock, who brought a copy from L.A. to play for his dumbfounded friends on the East Coast. “[N.W.A] was like the British Invasion for black people,” Rock said.

100 Greatest Hip-Hop Songs of All Time

The Notorious B.I.G., “Juicy”

The greatest rapper who ever lived, at his absolute peak: hilarious, incisive and insanely inventive as he balances urban realism (“Birthdays was 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 of his 1993 debut single, “Party and Bullshit,” and a far cry from the gangsta-don image he originally wanted to project. But executive producer Sean “Puffy” Combs insisted Big flow over a simple, club-friendly loop of Mtume’s early Eighties dance-party jam “Juicy Fruit.” (Producer Pete Rock says Combs got the idea 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.” 

100 Greatest Hip-Hop Songs of All Time

Public Enemy, “Fight the Power”

Hank Shocklee, one half of Public Enemy’s production team the Bomb Squad, said the group wanted their track for Spike Lee’s explosive 1989 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, as the Bomb Squad spun layer upon layer of samples (James Brown, the Dramatics, Uriah Heep) into implosive war-dance funk. Chuck D came up with the song’s concept while on tour with Run-DMC in Italy, and Lee directed its frenetic protest-themed video, which was filmed on the streets of Bed-Stuy, Brooklyn. The result was the total in-your-face package. In the summer of ’89, it seemed like it might start a full-on revolution.