Originally published for Vulture on September 14, 2020.
85. Jay-Z ft. UGK, “Big Pimpin’” (1999)
The ’90s ushered in both the rise of the South, which demanded acknowledgment of its contributions to hip-hop, and the emergence of the video vixen. It was only natural, then, that the Roc-A-Fella duo of Dame Dash and Jay-Z would extend an olive branch to UGK, one of the fastest-rising duos from Texas at the time, to collaborate on the biggest single of Jay-Z’s fourth album, Vol. 3… Life and Times of S. Carter. The song almost didn’t happen, however: Reluctant to collaborate with Jay, Pimp C didn’t submit his verse until the 11th hour, even delaying participating in his now-infamous music-video scene with Gloria Velez. (He ultimately had to film in Miami in lieu of Trinidad’s Carnival, the backdrop for the rest of the crew.)
76. N.O.R.E., “Superthug” (1998)
With one single and a comically bizarre video, N.O.R.E. not only established himself as a viable solo act after Capone-N-Noreaga but put the still-obscure Virginia production duo of Pharrell Williams and Chad Hugo, known as the Neptunes, on the map — gaining them the attention of none other than Michael Jackson. This song single-handedly created waves across genres, and Pharrell would go on to lay his fingerprints across some of pop culture’s biggest hits from Britney to Beyoncé, and more or less trademarked N.O.R.E.’s “what what!” catchphrase as a New York rap siren.
60. Black Rob, “Whoa!” (2000)
With iconic Buckwild sampling production that still gets played out of car speakers during Harlem and Bronx summers, the assist from the legendary Diggin’ in the Crates Crew flipped François Valéry’s “Joy” to give Black Rob his biggest hit as a lead artist to date, filled with stream-of-consciousness ad hominems.
57. The Notorious B.I.G. & Lil’ Kim (Junior M.A.F.I.A.), “Get Money” (1995)
Junior M.A.F.I.A. was a hip-hop collective of young adults from Brooklyn who were brought together and molded by the visionary eye of the Notorious B.I.G. and made their own mark with their debut album Conspiracy. They also introduced the world to Lil’ Kim — a young woman with magnetism and a commanding flow that consistently placed her toe to toe with her male peers. Nowhere is that more evident than on “Get Money,” an enthralling duet with a counterpunch, timbre, and cadence that has her four-foot-11-inch frame at parity with one of the best storytellers in hip-hop history, Biggie himself.
54. Azealia Banks, “212” (2011)
In New York, your area code is just as fundamental to your hometown pride as any other locality marker. No one knows that better than Harlem-raised Azealia Banks, who wrote the hit in reference to Manhattan’s premier three digits while living on Dyckman. Banks burst onto the scene at the top of the decade as a boundary-breaking force, interpolating her skillful raps with beat structures emerging from ballroom culture — no one else does Hot 97 Summer Jam and Mermaid Ball in the same day — while sharing just a flash of the vocal dexterity that is part and parcel of her avant-garde sonic universe.
46. Foxy Brown, “Ill Na Na” (1996)
“Ill Na Na” is a lightning-in-a-bottle moment in hip-hop. It’s like listening to a time capsule where Foxy — a spitfire out of Brooklyn who stunned the scene with her verse on LL Cool J’s “I Shot Ya (Remix)” as a teenager — and Lil’ Kim are still friends and collaborators, and women were going platinum off physical sales on their debut albums. A brazen Inga Marchand made her stamp, inverting misogynist tropes into husky, unapologetic rejoinders anchored by the closest approximation of a heartthrob in ’90s rap, Method Man.
25. Lil’ Kim, “Crush on You” (1996)
Stepping out from Junior M.A.F.I.A. with the mentorship of the Notorious B.I.G., Kim sought to continue to subvert the expectations of women in rap with the unblushing, aggressive lyricism of her debut solo album, Hard Core. “Crush on You” made it clear that her role was not to follow a blueprint but to stencil a new template — joining forces with stylist Misa Hylton to pair her and Lil’ Cease’s lavishly bawdy verses with richly pigmented ensembles and visuals, down to the matching wigs. With one video, Kim melded street fashion with hip-hop on the mainstream stage.