May/Joey Aich/Dewie Lennon/Ray Ave/DeVere/northcoastWill

On its latest album, Summer Planning, May explores painfully honest hopes and dreams. The 20-year-old rapper spills his ambitions in tracks like "Big Dreams," on which his wish-list lyrics penetrate over deep synth waves. The album plays out with mostly slow beats with few exceptions, but May's rapping keeps it interesting. On the stand-out track, "Black Roses," he weaves his lyrical ingenuity around the beat with a skillful execution. A young rapper with dreams of being famous may seem like an all-too-common trope, but May might just pull it off. Tonight's line-up includes a host of other Cleveland-bred rappers, all nursing the kind of passion only capable within an artist early in his or her career. (Patrick Stoops)