As a young MC who applies crisp cadence and acrobatic flow to lean and punchy rhythms, Jackboy swiftly established himself as one of trap’s tightest new talents when a freestyle over Bobby Shmurda’s “Hot N*gg*” caught fire online in 2016. It didn’t hurt when he got some shout-outs and mixtape guest spots by Kodak Black, who grew up with Jackboy—born Pierre Delince in Haiti in 1997—in Pompano Beach, Florida. And though Jackboy’s troubles with the law kept him from putting all his time and energy into music, he still evolved into one of the most versatile talents on Kodak’s Sniper Gang roster over the course of his mixtape releases and hard-hitting tracks like “Bipolar” and “Pressure,” two vivid accounts of his struggles to escape the thug life. Released in 2020, and featuring appearances by Lil Sean, YFN Lucci, and Kodak Black (the moody “Like a Million”), Jackboy’s self-titled debut album shows just how much he’d grown on tracks that combine trap’s trademark toughness and bass-heavy bounce with a bounty of melodic hooks and countless lyrical twists and turns. Jackboy quickly followed it up with Living in History, a powerful set that combines his poignant reflections on his painful past with musical ideas that expand trap’s stylistic boundaries while preserving its raw power.