100 Greatest Hip-Hop Songs of All Time

The first national Miami bass hit came from Lady Tigra and Bunny D, teenagers with personality for days who met as dancers on a local TV show and had rhyme battles with boys in the high school lunchroom. “When I was singing ‘Grab it like you want it,’ I didn’t know what the hell I was talking about,” Tigra recalled. “We were virgins!”

“Get Low” was the Number Two hit that signaled the peak of the high-energy, high-alcohol-content, shout-happy movement known as “crunk.” Ying Yang Twins brought the “to the windows, to the walls” hook (originally a black fraternity chant), and yowler-producer Lil Jon flipped it into over-the-top party music.

Maya Arulpragasam was a globally connected radical who turned into one of hip-hop’s most forward-thinking artists. “Paper Planes” was a Clash-sampling shot at immigrant-fearing Westerners, complete with gunshot sound effects. In 2008, it blew up into one of the unlikeliest Top 10 jams ever. “[It’s] my underdog song,” she said, “but it’s become the biggest song.”

This towering New York anthem began as a demo by Angela Hunte, who grew up in the same Brooklyn building as Jay Z, and Jane’t Sewell-Ulepic. With a vocal from Keys, the song took on an angelic power. “Even amongst all that dark and destitution, there’s that underlying possibility that you just might be able to do it,” Keys said. “That’s what the song is about.”

An Afrocentric crew who rapped about not dating crackheads were hardly natural stars. But Brand Nubian were so good they made it seem like a sure thing. Producer Sadat X couldn’t get the “what I am” refrain from Edie Brickell’s 1988 hit to fit an Ohio Players drum break, so he brought a vocalist in to sing it, not that anyone noticed.

Non-album single, 1996
One of hip-hop’s most powerful mourning anthems put Midwest hip-hop on the map. At the time, Bone Thugs had lost several loved ones, including Eazy E, who signed them in 1993. “To this day, when we perform it,” said Krayzie Bone, “there will be, like, 20 people in the crowd crying.”

After years in the industry shadows as a producer-writer-guest, Elliott emerged as a singular hip-hop figure with “The Rain.” Timbaland’s stop-motion digital syncopation and her giddy vocal gymnastics gave the song a playfully futuristic tint that Hype Williams’ groundbreaking video only enhanced.

The Oakland collective’s lone hit was a transporting blast of youthful talent. Over amped-up sax and marimba, A-Plus, Tajai, Opio and Phesto traded flicking, word-spilling vignettes with uncanny exuberance. “Now you have younger generations who were born in ’93,” said Phesto. “They’re like, ‘ ’93 ’til infinity.’ It means so many different things to so many different people.”

“There’s no way we’re gonna sell this album ’cause all of the songs are so street,” said Cash Money producer Mannie Fresh of rapper B.G.’s fourth LP. “How do we get him to everybody?” The answer was “Bling Bling,” which hooked a diamond-studded slang term to a synth-y bounce and landed it in Merriam-Webster’s dictionary.

Teenage producer Lex Luger came up with more than 200 beats in a week, one of which became the backdrop for Ross’ high-def hustler fantasy “B.M.F.” Ross compares himself to drug lords like Chicago’s Larry Hoover and Detroit’s Big Meech, who later called the song “a priceless way of recognizing and paying homage to me and the B.M.F. family.”

Rotund, uproarious Biz Markie is one of hip-hop’s most lovable figures. For “Just a Friend,” he donned a powdered wig to play piano in the video and bellowed an outlandish interpolation of Freddie Scott’s 1968 soul hit “(You) Got What I Need.” Said Biz, “I tried to get Al B. Sure! and I tried to get Keith Sweat but they were busy doing their stuff, so I said I’ll do it.”

Before his sudden death in 2007, rapper Pimp C celebrated his release from jail with this lush posse cut: Houston’s reigning hip-hop duo UGK were joined by fellow Dirty South crews Outkast and producers Three 6 Mafia for a celebration of playalistic splendor over a sweet sample from the soundtrack for the blaxploitation film The Mack.

“[‘The Bridge’] was the first ‘rep your hood’ record,” recalled MC Shan. With a James Brown-sampling beat from Marley Marl, this ode to Queensbridge instigated a full-blown regional war when the Bronx’s Boogie Down Productions released “The Bridge Is Over.” Things got so heated that Marley claimed BDP made their record using a stolen reel of his drum sounds.

Digital Underground mastermind Shock G wrote the bass line for this funky free-form party jam and invented a fictional fake-nosed character named Edward Ellington Humphrey III to perform it. “I said that he was my brother from Tampa, an ex-lounge singer who got in a grease accident in the kitchen,” he said. “And people were buying that shit.”

Atlanta producer Dupri built his Nineties success on poppy hits like Kris Kross’ “Jump,” so his record label didn’t consider a collaboration with Jay Z mainstream enough to be a single. But with a hot beat and classic Jigga lines like “I’ve been spending hundreds since they had small faces,” “Money Ain’t a Thang” blew up all the same.

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.

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).”

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.”

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.

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.”

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.

“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.