Songfacts®:

• This waltz time shanty sing-along finds White singing of heartbreak, as the newly-single protagonist of the song adjusts to their new status. He is joined on harmony vocals by Pokey LaFarge and Ryan Koenig of St Louis-based American roots band Pokey Lafarge and the South City Three. White told NME: "This is one of my favorite things on the record. I did it with this band called Pokey Lafarge and the South City Three. I just played piano with them, and overdubbed the drums later. It's the only song on the record that I play drums on."
• Pokey LaFarge told Uncut: "There's so much clarity in Jack's music. When he sings, the voice and the music are true. I started working with him back in 2011, just before the recording of Blunderbuss. He basically wrote and arranged I Guess I Should Go To Sleep before our eyes, right there in the studio. We did maybe two or three takes at the most."