Chance the Rapper
In the midst of skyrocketing murder rates and the drill craze, Chance the Rapper decided to stay positive. When his breakthrough Acid Rap mixtape dropped in 2013, it was tough to pin down exactly what you were listening to. Chance blended soul, gospel, funk, and hip-hop into a glorious mix that hadn't been heard in the Midwest since Common, Lupe Fiasco, and Kanye had the world by its ear.
His current Social Experiment is taking things even further, with Arthur theme song remixes, a full band, and the liberating absence of a record label. Chance's voice, too, is a breath of fresh air: hyperarticulate and brimming with emotion, he provides a counterpoint to Chicago's militarized rap scene. While Young Chop, Chief Keef, and Lil Durk have spread their music amongst the neighborhoods that inspired it, Chance's decision to go against the grain and spread love has gained him diehard fans.
Though his music runs counter to Chicago's current style, he's actually one of the purists on this list. He's a self-professed student of Chicago's conscious rap era. He also lists Eminem (Detroit) and Lil Wayne (New Orleans) as early influences, but it was Kanye's instrumentals Chance chose for his first freestyles. By bringing Chicago's history back to the fore, Chance is breaking boundaries as much as any other rapper on this list. And he's earnest, evolving his style since he was a part of Instrumentality back in 2009: