Jake Cassman’s “Trying to Mourn a Friend of Mine” is the kind of song that sneaks up on you, like a deceptively simple tune that grows deeper and more affecting with every listen. Rooted in an acoustic strum that runs like a literal heartbeat through the track, it’s a raw, heartfelt, and refreshingly human reflection on loss, connection, and the strange contradictions of mourning. Released as a prelude to his upcoming debut LP Idling High, the song feels both like a continuation of Cassman’s musical journey and a bold detour into new territory.

Cassman has long been a songwriter who sits comfortably between worlds blending the unvarnished storytelling of Americana with the energy of indie rock and the earworm hooks of power pop. That hybrid sound remains intact here, but “Trying to Mourn a Friend of Mine” strips things down to their essence. Built around that steady 1-2 acoustic strum, the track’s arrangement is beautifully unpretentious. It features no unnecessary frills, no grand crescendos, just Cassman’s voice carrying the emotional weight. It’s the definition of less being more!

His vocals are electric; playful yet pained, confident yet cracked in all the right places. There’s a vibrant intensity to his performance that captures the surreal dissonance of grief. Even as he sings about loss, there’s an undercurrent of vitality in his delivery, a reminder that love and life persist even in the shadow of death. However, it’s those mini moments in between where he grits his delivery and literally has you on edge as things take a turn for the intense.

Musically, he still finds room to surprise. The song’s subtle indie rock flourishes, those fleeting instrumental breaks and melodic pivots that you’ll experience, keep the listener on their toes. They’re like flashes of color amid the grayscale of the subject matter. The production walks a fine line between intimacy and expansiveness, creating a sound that feels like it could fill a small club or echo through a festival field.

Idling High is shaping up to be the grand statement of Cassman’s career and “Trying to Mourn a Friend of Mine” is the song that shows his heart at its most exposed. It’s the sound of an artist confident enough to be vulnerable, to explore the messy in-betweens of joy and pain without dressing them up. We’ve reviewed him in the past, and as he continues to release, the showmanship continues to evolve in the best way possible.

Go ahead and make sure to check this out, but for your own sake, don’t miss out on all the other gems surrounded in his discography. Click those links below to listen in and follow along!

Listen to “Trying To Mourn A Friend Of Mine”

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Jake Cassman finds beauty in grief on “Trying to Mourn a Friend of Mine”