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The 100 Best Rap Singles of 1990

The 100 best rap singles of 1990 found the hip-hop nation reckoning with an audience that may have not fully appreciated Black culture.

We all know the tale of Vanilla Ice: Even now, he remains the personification of unalloyed wackness. But his ascent to the top of the Billboard charts was buoyed by a stream of pop-rap pablum. It wasn’t necessarily the worst, like Candyman, that was the problem; it’s that it seemed to define rap’s mainstream profile. Some pop-rap hits from that era like Mellow Man Ace’s sly, witty “Mentirosa” were unfairly maligned as novelties. But it’s easy to sympathize with hardcore rap fans who grew sick of MC Hammer and sundry hip-house and New Jack lightweights hogging radio spins and MTV airplay. Years later, Nas complained that rappers couldn’t put out albums without adding a hip-house cut for UK club DJs to remix.

Meanwhile, gatekeeper critics grew increasingly disturbed with misogynist lyrics in hardcore rap. They chafed at how NWA and former member turned “Benedict Arnold” Ice Cube seemingly treated women as potential sexual conquests and “bitches.” Geto Boys’ self-titled third album, a re-release of 1989’s Grip It! On That Other Level was already generating heat in the press, even though it wouldn’t become a national controversy (and a fetish object for ghetto safari jerks) until the following year. Public Enemy elicited awe for their undisputed musical excellence and criticism for their odd embrace of bizarre conspiracy themes. Meanwhile, X-Clan and Paris made enemies by deploying Black nationalist code phrases like “cave boy” and “devil.”

Then there were emerging scenes in the South and elsewhere angling for a seat at the table. The 2 Live Crew are now respected (albeit grudgingly) for their pioneering bass tracks, but at the time they were dismissed as smutty idiots that accidentally found redemption as free-speech warriors. It’s also worth remembering that, after an indie-label buying spree a few years back, major label corporations controlled most hip-hop output of note, leaving unsigned acts — especially those outside of New York and L.A. — to struggle on the margins. This would begin to change in 1991-1992 as musicians launched underground imprints to avoid being compromised by A&R executives “looking for a suit-and-tie rap that’s cleaner than a bar of soap.”

With so many crosscurrents circulating in the genre, hip-hop as an art form was due for an evolution. Vanilla Ice’s “Ice Ice Baby” was just a tipping point.

When compiling this survey, the first source I turned to was Ego Trip’s Book of Rap Lists. It certainly helped figure out which tracks to include — and which to omit.

1990 was long before the World Wide Web. Same-day release dates were often buried in music-industry journals, radio reports, and other print matter that’s difficult to find now. Publishing and copyright dates don’t necessarily indicate year of release; a 12-inch single copyrighted in 1989 may have actually hit the market in January 1990. And Wikipedia’s user-generated hodgepodge of carefully documented facts, estimates based on incomplete data and pure wishful misinformation makes it an unreliable source. (I conducted research using Discogs as well.)

Other cases called for a personal decision. Queen Latifah’s “Ladies First” was released on December 16, 1989; it entered the chart the following month. (Inexplicably, the Ego Trip crew didn’t include this classic on their Greatest Hip-Hop Singles lists.) I remember distinctly when “Ladies First” exploded in popularity in the spring of 1990. I used the Billboard date.

This is an era that predates streaming, when every song will blast onto the U.S. charts the week an album is released. Back then, record labels carefully staggered single drops to extend an album’s life cycle. Def Jam, for example, spent over a year issuing seven radio hits from LL Cool J’s Mama Said Knock You Out.

But this list isn’t meant to supersede any other. At 100 singles, I simply hope to tell a deeper story. (I also included Ice Cube’s “Jackin’ for Beats,” which got a video treatment but was never released as a single.) I feature overlooked releases like Mac Dre’s first EP, Young Black Brotha; and Dan the Automator’s second EP, King of the Beats. I tried to avoid lesser singles by famed Golden Age heroes in order to expand the roster of names: sorry, no Boogie Down Productions’ “Ya Know the Rules.” With luck, these entries comprise a narrative of a genre in flux at the dawn of what is arguably its most important decade.

Finally, Critical Minded readers know that I don’t use rankings in lists. From my perspective, ranked lists should be made by committee, not one person’s opinion — though I acknowledge that the latter is probably more fun. I hope this technique allows you to focus on all the pieces of the puzzle.

The 100 Best Rap Singles of 1990 (in alphabetical order; click on links for more on each entry)

Originally published on This post has been updated.

Chuck D photo by Paul Natkin/Wireimage.
LL Cool J photo by Chris Carroll/Corbis Entertainment/Getty.
Ice Cube photo by Kevin Cummins/Getty.
Queen Latifah album photo by Bart Everly.


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