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."
Robin Thicke and his mom, Gloria Loring are the first the first ever mother-and-son to have both tallied top 10 singles on the Hot 100 as solo artists or duos. Loring reached #2 with Carl Anderson in 1986 with "Friends and Lovers" and Thicke topped the chart in 2013 with "Blurred Lines."
Two tears roll down Sinead O'Connor's face. toward the end of the video for "Nothing Compares 2 U." They were shed because she associated the song's lyrics of love and loss with her mother, who was killed in a car accident in 1985.