Sleepy Hallow

When Sleepy Hallow’s “Deep End Freestyle” started catching on social media in early 2020, it seemed like the perfect encapsulation of Brooklyn drill: minimal, melodic, and intense—and at two minutes, the kind of track that begged to be played back-to-back-to-back. Born Tegan Chambers in 1999, Sleepy—alongside frequent collaborator Sheff G, producer Great John, the late Pop Smoke, and others—has emerged as one of the freshest voices in New York hip-hop, providing solid counterprogramming to a landscape still mostly dominated by trap. As a rapper, he’s mercurial but spirited, throwing himself into different flows and rhythmic pockets with an enthusiasm that makes even his most threatening verses light up with a kind of happy mischief (“Tip Toe,” “Baddie Betty Boop”). And though he continues to represent Flatbush and Brooklyn drill, his sound has gotten increasingly diverse, dabbling in Latin pop (“Breakin Bad”), New Agey atmospherics (“Molly”), and guitar ballads (“Weight on Me”)—proof that he can represent his scene without being confined by it.