When medieval painter Hieronymus Bosch begins courting Anna, he feels he must hide the many odd creatures living in his house, a result of his over-active imagination. Anna soon discovers them but is instantly won over by the cute Sophie, and funny Otto and Gregor. As Hieronymus' imagination leads him deeper into trouble, he abandons it for a time, denying the existence of his beloved creatures.

An emotionally powerful and intimate musical about two New Yorkers in their twenties who fall in and out of love over the course of five years, The Last Five Years' unconventional structure consists of Cathy, the woman, telling her story backwards while Jamie, the man, tells his story chronologically; the two characters only meet once, at their wedding in the middle of the show.