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As a result of Leonard Bernstein's numerous didactic lectures, he is generally recognized as a tonal composer who misrepresented or even misunderstood other compositional grammars. But, while scholars criticize Bernstein for these reasons, close analysis of his own music reveals a different story. Using post-tonal theory and semiotics, I examine Bernstein's music from the perspective of compositional grammars—some not tonal—through analysis of three pieces from West Side Story (1957), 'The Rumble,' the 'Tonight' ensemble, and the 'Cool Fugue. I demonstrate that although Bernstein passionately defended tonality as the means to unite composers and audiences—especially Broadway audiences—analysis of West Side Story reveals varied musical syntaxes, including particular intervallic structures, pitch centric passages, and twelve-tone serialism. Analysis of West Side Story challenges illusory notions of supposed binary oppositions: opera versus Broadway, highbrow versus lowbrow, and tonal versus atonal. By closely interpreting how various compositional grammars in West Side Story blur supposed opposing binary musical aesthetics, genres, and styles, this thesis opens new and perhaps unexpected avenues for Bernstein research.