Wonderful Town began as the hugely-popular 1940 Broadway play My Sister Eileen, the story of two sisters from small-town Ohio, hoping to find a place for their talents in New York's Greenwich Village. Written by Joseph Fields and Jerome Chodorov, the play was based on the autobiographical stories of Ruth McKenney published in The New Yorker during the 1930s. The rights to a musical version were acquired by Robert Fryer, who then took it to the director George Abbot. Fields and Chodorov adapted their play into a libretto and Leroy Anderson and Arnold Horwitt wrote the score.

However, the score was less-than well-received, and with just five weeks before rehearsals were to begin, director Abbot asked Bernstein to bolster it with some additional numbers. Bernstein declined, but offered to compose an entirely new score in conjunction with Adolph Green and Betty Comden. Abbot acquiesced, and with the addition of choreographer Jerome Robbins, it became a reunion for the creators of the musical On the Town.

Given the speed in which Wonderful Town was composed, there is a natural sense of spontaneity and freshness to Bernstein's music and Comden and Green's lyrics throughout. The screwball tale of Eileen and Ruth Sherwood and their colorful adventures in New York was matched by Bernstein's exuberant, jazz-based score, which embraces conga, swing, and ragtime forms. Eileen's beauty enslaves half the men in the city, including the police force, as suggested in the witty "My Darlin' Eileen." Ruth, on the other hand, is sweetly sentimental, with dreams of becoming a successful writer, reflected in "A Little bit in love." All of the larger-than-life characters come together in the brash show-stopper, "Christopher Street," while other great vocal moments include "Conga!," "Ohio," "One hundred easy ways to (lose a man)," "Conversation Piece," and "Pass the Football." Instrumental numbers such as "Conquering New York," "Entr'acte, " and "Quiet Incidental," showcase Bernstein's breezy, spirited melodies.

Wonderful Town was partially a star vehicle for Rosalind Russell, who was featured in a nonmusical film version of My Sister Eileen in 1942. The musical received favorable out-of-town tryout reviews before opening to critical raves at the Winter Garden Theater on Broadway in 1953. A respectable total of 559 performances, a Tony Award, and a 1958 TV version followed.

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