One of several surprises on a first listen to Helplessness Blues is the burst of free-jazz sax that tears into the fabric of this multi-part song. "I was listening a lot to Ascension, by John Coltrane and Alice Coltrane," frontman Robin Pecknold explained to The Independent. "I don't have a ton of experience with that kind of music, but I would put that record on and I liked the way it would just elicit different emotions in me – I'd have this pumped-up energy, like this weird anxiety. I was really into that, the way that music can be capable of producing that feeling. In the context of that song, it's like the different phases of a break-up, so I thought the music in every different section should have the appropriate emotional feeling: the beginning feels really nostalgic, and there's a section in the middle that's loud and rougher, then it goes to this solitary place, then ends in this argument. I was just trying to capture the different phases of a break-up in one song."