Jake Cassman’s upcoming album Idling High (due out November 14) already promises emotional punch, and his new single “Trying To Mourn A Friend Of Mine” makes good on that promise in full color. The track leans into a vaudeville-tinged groove — a skank rhythm on acoustic guitars, a percussion section that pops and sways, and a vocal performance that feels straight out of another era. It’s theatrical without being showy, letting Cassman’s raw emotion and vivid storytelling lead the way. The recording sounds delightfully unpolished, as if captured in a single breath — alive, human, and a little haunted. Lyrically, it’s a meditation on loss that refuses to stay still, moving from aching remembrance to dark humor and back again. By the time you hit the song’s final verse, the lyrical twist lands like a jolt — it’s the kind of reveal that makes you hit replay just to be sure you heard it right.

“Trying To Mourn A Friend Of Mine” leaves you leaning closer, ready for whatever Idling High has waiting around the bend. Listen to it now: