Since rising up out of the eastern Toronto suburb of Pickering in the late 2010s, Jon Vinyl has turned relatable emotions into a prolific career making, as his social media profiles put it, “R&B songs you can relate to.” Heartbreak Hill arrives in the wake of two Juno-nominated projects—2021’s Lost in You and 2022’s PALISADE—that established him as a singer who’s unafraid to be intimate and honest. This brief eight-track status update shows him becoming ever more adept at initiating difficult conversations within ever-so-smooth songcraft.