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.”