"Smallest Wingless", which the Western "Gazette" has called one of Cardiff's most popular songs, was inspired by a photographer friend who worked closely with Now I Lay Me Down To Sleep, a non-profit organization that provides families of babies who are stillborn or are at risk of dying as newborns with free professional portraits with their babies. Cardiff's song tells the story of two parents welcoming a newborn into the world, only to be told that the child will only survive for a few hours. "A lot of people share their experiences with me in regards to that," Cardiff has said of the song.