Bennett did his first theater orchestrations in 1920 and quickly rose to pre-eminence in his field, sometimes working on more than twenty shows a season. As Broadway’s leading orchestrator, he worked with Jerome Kern, Irving Berlin, George Gershwin, Cole Porter, Richard Rodgers, Frederick Loewe and others on more than 300 shows between 1920 and 1975. Unlike most of his commercial-arranger colleagues, however, he never lost sight of his "serious music" aspirations, concerned as much then with conducting or criticism as with composing. With some apprehension, he put his arranging on hold in 1926, departing with his family for study abroad. Excepting a few forays to London or New York to do theater orchestrations (including Kern’s 1927 Show Boat) Bennett spent the late 1920s in Paris and Berlin. He studied with Nadia Boulanger, who praised him as "a true artist," and assured him that he could maintain his artistic ideals while supporting his family with his commercial work. Recognition for his creativity soon came in the form of an "honorable mention" (for his first symphony) in Musical America magazine’s symphonic composition contest. Between commercial assignments, he completed nearly 200 original works — symphonies, operas, chamber music, choral and vocal music, and more than two dozen pieces for wind band.

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