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Like Fancy Free, On the Town tells the story of three sailors during World War II and their amorous adventures on a 24-hour shore leave in New York City. The framework of a full-length musical piece, however, permitted the development of complete characters, comic situations, and a distinct theatrical personality. This personality, a rare combination of lighthearted and passionate, derived from the dramatic demands of time juxtaposed against the ominous background of the war. Surely, the personalities of its authors also influenced the show's singular identity. Furthermore, Comden and Green insured that the spirit of their writing would come to life by playing Claire and Ozzie themselves.
Variety Magazine announced the show on June 7, 1944 saying, "...a group of youngsters have gotten together to stage a musical production. On the Town, scheduled for Broadway this fall will be written, produced and staged by 23 to 25 year-olds headed by Leonard Bernstein, who recently has forged to the front of the ranks of young symphonic composers and conductors.