The song originated with Leslie Feist meeting Ron Sexsmith at a party in Ottawa. Feist asked Sexsmith about the Brandy Alexander he was drinking. Sexsmith told her the story of Lennon and Nilsson at the Troubadour.
"Three days later, I received an e-mail from her with this lyric in it," Sexsmith told the Montreal Gazette. Sexsmith composed music for the song.
Feist released a version of the song on her platinum-selling album The Reminder. Sexsmith recorded his own, more upbeat, version for his Exit Strategy of the Soul album.