The album was originally conceived as a music revue. Stephin Merritt was sitting in a gay piano bar in Manhattan, listening to the pianist's interpretations of Stephen Sondheim songs, when he decided he ought to get into theatre music because he felt he had an aptitude for it. "I decided I'd write one hundred love songs as a way of introducing myself to the world. Then I realized how long that would be. So I settled on sixty-nine. I'd have a theatrical revue with four drag queens. And whoever the audience liked best at the end of the night would get paid. " He also found inspiration in Charles Ives' 114 Songs, about which he had read earlier in the day: "songs of all kinds, and what a monument it was, and I thought, well, I could do something like that. "