Just as Bernstein’s classic musicals On the Town (1944), Wonderful Town (1953) and West Side Story (1957) are known for their complex, vibrant scores and glorious dance numbers, all three also share another central component: their New York City setting. In each of these musicals, New York itself functions like a character in the show, with each musical reflecting a different aspect of the Big Apple. Let this be your guide to New York City through the lens of Bernstein’s musicals.

Wonderful Town (1953)

Goodman Theatre’s upcoming revival of Wonderful Town will capture the vivacity and livelihood of New York as a city where dreams come true. While the show was originally set in the 1930s, the Goodman’s production will transport audiences to 1950s New York—a stable, post-war moment for the city. Sisters Ruth and Eileen Sherwood come to New York hoping to strike it big—Ruth dreams of being a journalist, while Eileen dreams of being a famous actor. The New York of Wonderful Town is a lighthearted one, teeming with energy and promise. The show’s opening number “Christopher Street” introduces the audience to an eccentric array of artists living in Greenwich Village, while the city’s hustle and bustle comes to life in the Act One finale “Conga! Swing!” in which Ruth encounters a group of visiting Brazilian cadets. The New York of Wonderful Town maintains an optimistic outlook throughout the show.

On the Town (1944)

Like Wonderful Town, Bernstein, Comden and Green’s first musical collaboration, On the Town, depicts New York City as an exciting place to be, buzzing with activity. In On the Town, World War II sailors Chip, Ozzie and Gabey are given a day of shore-leave in the city. The opening number “New York, New York” has a celebratory tone that captures the cacophony of city life and the possibilities that 24 hours there can hold. At the same time, the complexity of this number (and the show’s score on the whole) echoes the seriousness and delicateness of the situation: these sailors may not have the opportunity to return to New York again. The New York City of On the Town is a transient place: these characters are just passing through, which is echoed in the number “Some Other Time,” in which Chip and Ozzie duet with their love interests Hildy and Claire about the fleeting moment of the day.

West Side Story (1957)

Unlike the glittering, lively New York of Wonderful Town and On the Town, West Side Story features a decisively grittier, darker depiction of the city. While the latter two shows focus on NYC as an exciting place of discovery, West Side Story provides a window into more unfamiliar elements and implies a threatening danger. The racial tensions between rival gangs the Caucasian Jets and the Puerto Rican Sharks provide a central theme in the show, and Bernstein’s music sounds jazzier than in either of the other two musicals. West Side Story’s score has a destabilizing sense to it that mirrors the harsh reality of the show. It is only when romantic leads and star-crossed lovers Tony and Maria sing that audiences hear the more traditional, polished vocals and music typical of the art form. Tony and Maria’s songs have a sense of timelessness unbound by a specific moment or location: songs like “Tonight” and “Somewhere” transport viewers to another world. And in that sense, the specific treatment of NYC in West Side Story remains dark and ambivalent—but, in Tony and Maria’s love story, a glimmer of hope remains.

See Bernstein’s musical vision of New York City come to life in the Goodman’s production of Wonderful Town. Performances start September 10! GoodmanTheatre.org/Wonderful Town