Since rising up out of the eastern Toronto suburb of Pickering in the late 2010s, Jon Vinyl has leveraged an early co-sign from his old high-school buddy Shawn Mendes 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. “Wasted” wafts in on a cool, seductive neo-soul beat, but its lyrics chronicle a vicious cycle of infatuation, insecurity, and insomnia. And while “Let This Go” takes its shoulder-loosening cues from the Black Pumas school of retro grooves, the song is steeped in simmering tensions and resentments. (“I’m just speaking from the heart,” Vinyl sings. “I can’t let this shit go.”) Heartbreak Hill’s outpouring of emotion eventually culminates in the exquisitely aching “Broken Hearts,” a heavenly piano ballad that feels like a last-rites recital for the failed relationship eulogized within.