While Bolton was still a student, his stories had been published in magazines. At the age of 26, he wrote his first stage play, "The Drone", in collaboration with Douglas J. Wood. His second play, "The Rule of Three" (1914), was written without a partner, but the following year he embarked on his first musical theatre collaboration, "Ninety in the Shade", with music by Jerome Kern, lyrics by Harry B. Smith and book by Bolton, first produced at the Knickerbocker Theatre, New York, on 25 January 1915. The same year, he wrote "Hit-the-Trail-Holiday" with George M. Cohan. That same year he collaborated with Kern and others on the musicals "Nobody Home" and the even more successful "Very Good Eddie", the first two "Princess Theatre musicals". The latter of the two was also a hit in London.