Kanye, Twista, R Kelly, Common... Chicago has made a name for itself, but for the most part the best shit always went under the radar and straight into the used bin. My Midwest cuddies could argue for days about who went the hardest in the Chi: the West or the Southside (totally pretending like the North doesn't even exist). But it's the Westside that produced Do Or Die and Psychodrama, the two hardest hitting Windy City rap groups in my opinion, so it's dubs up, period. Do Or Die are known for their collaberations with Twista way back but it's their mix of soulful hooks and legit street credibility, THE rarest element in hip hop these days, that got their name on the tongues of true heads. Chicago is a money making city. The gangs don't just put on bandanas and write on walls. Motherfuckers had whole project units turned into drug distribution centers the one time couldn't even infiltrate. Pimpin was as accepted as going the school route and it's just as common to see dudes banged out with canes and hats as it is a bomber jacket and a fitted. The West Side was the epicentre of pimpology. Do Or Die lived that, and they literally exhale legit swag.
Do Or Die - "Po Pimp"