When De La Soul, Talking Heads, No Doubt, Bobby Caldwell, Human League and about 30-40% of the cuts mentioned here are considered nerdy and unhip, I'll chalk it up to generational differences...most of them released several crossover hits.
My thoughts go along the lines of artists who made one song so TOTALLY different than their usual genre and it crossed over into the hood...
For example...if you're from Chi and are an ol school stepper, two of the stepping anthems are Logins and Messina's Pathway to Glory and Cat Stevens' Was Dog a Doughnut.
Both artists were mainly folk, pop stars and to my knowledge never made anything as funky as these two cuts..