De La Soul + Taylor Bennett

Long Island trio De La Soul's 1989 debut 3 Feet High and Rising is among the rap genre's most vaunted records, harnessing an inspired collection samples and introducing comedic skits to the hip-hop vernacular. Even 30 years after its release, it's an album that sounds ahead of its time—albeit one that you can't easily stream, thanks to the group's fractured relationship with its label, Tommy Boy Records. While younger audiences likely know Posdnuos, Trugoy and Maseo for their collaborations with Damon Albarn's Gorillaz project, we're hoping that De La Soul digs into the classics during their Taste of Chicago set, which features an opening set from local rapper Taylor Bennett.