Bernstein’s later Broadway shows, West Side Story and 1600 Pennsylvania Avenue, represent his greatest smash hit success and his biggest flop. This chapter focuses on the music of these two shows, and more specifically on what happened to the music after the initial runs were over, when the theatres went dark, and how, in both cases, the music became abstracted from its original context through arrangements, cover versions, and use in advertising, film, and television, sometimes reframing the meaning of the original material. As is to be expected, the two stories are quite different: West Side Story has become deeply embedded in the culture while 1600 Pennsylvania Avenue was nearly banished to obscurity. The reception of both shows, however, reveals something about the enduring nature of Bernstein’s music.