Tom Ewing’s Top 100 Singles Of The 90s

Lyrically this seems negligible, even laughable: the first big gangsta piety hit, wherein Coolio delivers a stern message to the youth, to mend their ways and not follow his path of violence and bloodshed. He does this by going on about what a hard bastard he used to be, obviously. This kind of O-Lord-I-have-sinned-but-hey-check-out-the-sins-dude repentance-rap ended up with the multiplatinum sobfest of “I’ll Be Missing You”, a continent-straddling tower of limply-rapped schlock, one of the few big 90s hits as bad as the hip kids claimed it was, and redeemable only for unwittingly exposing how mealy-mouthed Sting’s original was.

But that’s the other thing Puffy’s monsterpiece shares with “Gangsta’s Paradise”, the wholesale kidnap and dusting-up of a hallowed tune. Stevie Wonder’s “Pastime Paradise” found him at his most easygoing and homilitic, but it also found him in possession of an absolutely spine-shuddering string arrangement that Coolio and cohorts are happy to seize on, burnish and darken. So even though it’s weapons-grade hokum, when you hear Coolio rap “As I walk through the valley of the shadow of death” with those great keening strings at his heels, you sit up and pay attention. It’s an opening in a thousand, 24-carat melodramatic cool, and the song goes on to deliver on it, playing you as slickly as the sampled crescendoes. By the finale, when digital-lunged fallen angels are left to bathe the beat in a swirling, inhuman, lament, you stand humbled in the presence of calculated, complete pop greatness.