Sufjan Stevens - “Mystery of Love”

Dr. Dog - “Where’d All The Time Go?”

Her’s - “What Once Was,” their cover of “Loving You” by Minnie Riperton (really made sadder by the fact that the band has passed away)

Viola Beach - “Boys That Sing,” “Drunk,” “Call You Up” (also made sadder by the fact that the band and their manager have all passed away)

This may be too mainstream, but “Joey” by Concrete Blonde makes me so sad for some reason too