Following the trajectory of Sondheim’s career, Careful the Spell You Cast shows how Sondheim has dramatized this process throughout his writing life alongside different collaborators. From his work as a lyricist with the musicals Gypsy and West Side Story through to his later collaborations with Hal Prince (Company, Follies) and James Lapine (Into the Woods, Sunday in the Park with George), this book reframes the established view through lyrical and structural analysis in relation to the characters within each of these celebrated works of musical theatre, arguing that Sondheim is, in the popular sense of the word, a romantic within the tradition of the Broadway musical.