Starting next week, we’ll unveil our big list of the Best Songs of the 1990s. In the run-up to the reveal, we’re featuring some of our favorite songs that didn’t make the list through our regular Track Marks feature.

When you think of rap in the ’90s, it’s understandable if jazz hip-hop trio Digable Planets doesn’t immediately come to mind. Just a scant few years after they released “Rebirth of Slick (Cool Like Dat)” in 1992, Biggie and Tupac would emerge as pioneers of the genre and the East Coast/West Coast battle would be underway, dominating much of the scene until Jay-Z took up the mantle towards the end of the decade. While the laid-back vibe of the group’s most popular single may have soon found itself out of step with its more confessional successors, who openly mined their own biographies for their biggest hits, the song’s insanely catchy horn hook and dizzyingly dense lyrics have a charm and swagger all their own (and aren’t above some playful boasting: “We be to rap what key be to lock,” Ishmael “Butterfly” Butler asserts at one point, and it’s tough to disagree, at least while the song is spinning.)

I was reminded of the song’s pleasures when it was used in two pieces of popular culture this year: first in the summer’s delightful if uneven indie Dope and then over a montage in David Simon’s masterful HBO miniseries Show Me a Hero. While the use in the first instance is mostly nostalgia-driven given that the plot is about modern high school students whose nerdery is largely based in fetishizing the past, particularly the ’90s, the second has some surprisingly emotional context. Up until that point Hero‘s nondiegetic music had been solely Springsteen and tied tightly to the ostensible hero of the show, Oscar Issac’s baby mayor of Yonkers Nick Wasicsko. But Digable Planets kicks in as the mostly minority housing residents show the white citizens who have been fighting the new construction around their homes in an effort to prove their ability to be good neighbors. It’s a sly move on the part of Simon and company, as it’s conceivable that said residents would be listening to such a track themselves in the same way Isaac’s do-gooder would be obsessed with the Boss. But it also tips its hat to the way black culture was beginning to blend into the popular consciousness, a trend that would continue through the ’90s and beyond.

The song, and group, is also notable for being one of the few rap outfits outside Salt-N-Pepa to showcase a female voice. While the lyrics that Mary Ann “Ladybug Mecca” Vieira spits aren’t gendered, it’s still refreshing to hear her chime in with the same confidence as the boys, particularly since the genre as a whole often does very poorly by women. In the end it’s this sense of togetherness and positivity that makes the song endure beyond its singular groove. Digable Planets never make clear what exactly the “dat” they’re cool like is. Which means it could apply to just about everyone.

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Sara

Sara is big into reading and writing fiction like it's her job, because it is. That doesn't mean she isn't real as it gets. She loves real stuff like polka dots, indie rock, and underground fight clubs. I may have made some of that up. I don't know her that well. You can tell she didn't just write this in the third person because if she had written it there would have been less suspect sentence construction.

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