Sleepy Hallow isn’t allowing legal issues to stop his musical output. On Wednesday (May 24), the Brooklyn rapper unloaded a new single titled “Pain Talk,” which features Lil Tjay. Produced by Great John, the collaboration sees the Winner’s Circle star getting introspective about the obstacles in his life.

“Feel like me and the judge in the race, if I crash, she gon’ lock me away, got a Perc’, I might pop it today, said I’d stop but I’m stuck in my ways, and I work like I’m tryna get a raise, she said, ‘If you loved me, then you would’ve stayed,’ I know what she feelin’, that’s played, I ain’t really tryna bring you pain, would you love me if I was a lame? That’d mean minus the watch and the chain, had no car? Had to walk in the rain?”

“Pain Talk” boasts a video that comes courtesy of Picture Perfect. The clip shows the artists in church during a funeral and surrounding a bonfire with a bevy of women in tow.

In 2021, Hallow liberated his debut studio LP, Still Sleep?, a 14-song effort with a single appearance from longtime collaborator Sheff G. In that same year, he dropped off a deluxe edition of the aforementioned album with added contributions from Coi Leray, Eli Fross, Skillibeng, and more. Since then, Hallow continued his momentum via loose drops like “Die Young,” “2 Mins of Pain,” and “Marie.” He also embarked on a short 2023 tour that included dates in Connecticut, Rhode Island, and Boston.

Hallow first began making waves with 2020’s Sleepy for President, a mixtape that was considered momentous for NYC’s drill scene. In addition to Sheff G, Foushée, Fivio Foreign, and Jay Critch contributed to the 12-track effort. Press play on “Pain Talk” below.