In my case study of Oh, Boy!, I argue that this is the first Princess musical to contain no “blue book” scenes (i.e. scenes of vaudevillian sketches interpolated into an otherwise unconnected plot). Kern and Saddler also expand the role of underscoring in this musical to smooth the flow from speech to song and back again. Not coincidentally, Oh, Boy! was the first original musical created for the Princess, and the first in which P.G. Wodehouse contributed to the drama as lyricist. The chapter begins with an examination of the collaborative process developed by Kern, Bolton, and Wodehouse. Turning my attention to the resultant product, I examine the plot in detail. Considering the character development—occurring mostly in song—I believe that we can interpret Oh, Boy! as satirical social commentary rather than pure farce. The incidental music reveals as much about the characters as the sung music, and Kern uses leitmotivs to create a layered drama. He even expands song structures to drive whole scenes. Taken together, these features of Oh, Boy! lead audiences to experience the show as a complicated, emotionally compelling story featuring true-to-life characters with which the audience can identify, in other words, a Little Theatre play.