This chapter examines the work of Stephen Sondheim. It begins with an extended commentary of his career, followed by details on productions, with data and song information. Sondheim moved at the age of eleven from Manhattan to Doylestown, Pennsylvania—Doylestown, the country home of Oscar Hammerstein 2nd. A friendship with young James Hammerstein led to a close teacher/student relationship with James’s father, the man who helped create the modern musical in his work with Jerome Kern and who over the next few years would write Oklahoma! (Rodgers: March 31, 1943) and Carousel (Rodgers: April 19, 1945).