Kanye West made his name in Chicago chopping up classic soul sounds the city was known for, then provided career-making assists that took a few of the artists on this playlist from South Side to worldwide. But his more crucial work was becoming a model for a generation of rappers who share his ambitious DIY spirit—a clear product of his hometown. Historically, Chicago hip-hop hasn't had much industry or infrastructure, so the scenes these artists have built up are a result of collaboration (Chief Keef and Vic Mensa, Chance the Rapper and Jeremih, Dreezy and Queen Key), as well as the ingenuity to build, rung by rung. From the gritty South Side realism that spans Valee and Keef to G Herbo, to the influence of Chicago house and juke on Vic and Chance, what defines and unifies Chicago hip-hop is not a style, but how its artists reflect all that the Chi is, and can be. Our editors regularly update this playlist—if you hear something you like, add it to your library.