Read This When You Wake Up

Sleepy Hallow has come a long way since his early days as a pioneer of New York’s drill rap subgenre alongside his pal Sheff G. The Jamaica-born, Brooklyn-raised rapper has since expanded his scope, showcasing a bevy of different flow patterns on his 2021 studio debut *Still Sleep?* and pop instincts on his 2023 effort *Boy Meets World*. On *Read This When You Wake Up*, Sleepy blends these two worlds together, cueing up booming, distortion-heavy beats on “Madness” and crooning about the high life on “Drowning (Beverly Hills).” He’s more comfortable in his singing voice than ever before, tapping into a newly discovered vulnerability that gives the work an almost tangible emotional catharsis.