Chicago rap music!
I am from Chicago but I dont listen to much Chicago rap. I’ve spent some time going to shows, and Chicago rap audiences can be live, even the backpacker ones. But I have less patience for lewd punchlines and freestyles over “Shook Ones” and all-city battles and “I do it for the culture, maaaan!” Ahh who am I kidding I love that bullshit.

Vakill’s album from 2003 has some pretty beats from the Molemen who are the 90s-worshipping beat team behind Chicago’s whole underground rep. They make pristine, lonely-sounding sampled beats that can be really achingly beautiful but also incredibly limiting and that is part of why they make me sad, I think. One of the best songs on Vakill’s The Darkest Cloud is called “Sweetest Way to Die.” Rapping about graf is sorta passe these days (there are like 60+ songs about tagging and cops and they all have 90s-style boom bap beats) but graf was always huge in Chicago, at least since I’ve been living there (age 10) so I gives a shit.

A few years back the sale of aeresol paint was outlawed within city limits. Just a few years earlier, William Upski Wimsatt had proposed a transformation: the creation of beautiful painted rooftops. Chicago, because of the importance of the El to public transportation, is a city of rooftops, where the train weaves in and out of residential and commercial neighborhoods, yellow brick and porches and tenements, old gothic architecture and crumbling ancient apartment structures, thin black smokestacks sticking up from the tar-covered surfaces like little asymmetrical top hats, bundles of wires wrapped around telephone poles; Wimsatt wanted to transform this urban canvas into public art murals. Needless to say this wasn’t a popular opinion among city officials, and spray paint is now banned within city limits. Still, Chicago has a reputation as a graffiti city; the presence of so many old warehouses and abandoned meatpacking facilities, what Upski called the “Urban Frontier” – essentially the no-man’s-land of the ancient metropolis – meant that there was a massive canvas available, much of which could stay up for years without anyone cleaning or painting over it.

In high school I used to take the cta bus home, because my mom’s apt. was a good two miles away. I still remember my friend 3rnesto positioning me so he would be hidden from the woman who lived across the street as he painted up the bus stop; sometimes she would come out on her stoop and yell at the kids to fuck up ‘your own damn neighborhood!” For a while it seemed like every other person in my high school was tagging, although most of them were toys, and then there was a split when the rich kids went off to college and stopped the game they had played, like they gave up playing instruments and gave up theater and went on to be econ majors or business majors and the rest of the kids were arrested or fell into other things or just kept at it. Graf is still all over the place in the city. Its less obvious now, but it’s still there.

Vakill – Sweetest Way to Die

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