Fancy Free was Leonard Bernstein's first foray into the world of the ballet, and it immediately became extremely popular. The work's timing was significant. It had its premiere on April 18, 1944, just weeks after the successful premiere of the "Jeremiah" symphony and shortly after his appearance with the New York Philharmonic on a nationwide concert broadcast late in 1943. This triple shot of Bernstein established him once and for all as a major player in the musical world.

The story of the ballet is a simple one, devised by Jerome Robbins. It takes place in New York City, where three sailors are on shore leave. While in New York, they meet three girls in a bar, dance with them, fight over them, and then realize how stupid it is to let women come between friends. The plot line was reused by Bernstein in On The Town, his popular first Broadway musical.

The music in Fancy Free is based to a considerable degree on popular styles of the day. This is heard at the beginning with "Big Stuff," a popular hit Bernstein recorded as a single later, made famous by Billie Holiday. The jazzy style of the piece was relatively new to both Bernstein's writing and to concert music in general—it had only been about 20 years since Rhapsody in Blue broke many of the boundaries between jazz and classical music. Bernstein continued to explore this influence in many of his subsequent works.

The structure of the work is designed with dance in mind; there is little connective tissue between the sections, which are bridged with solo piano music. The sections include music derived not only from jazz, but also from styles ranging from Stravinsky to vaudeville. This kind of combining of styles is pervasive in Bernstein's writing; it continues in his later works, such as Facsimile, Candide, and the Mass. The music from the ballet was made into a concert suite for orchestra by Bernstein. The suite has six movements: "Dance of the Three Sailors," "Scene at the Bar," "Pas de Deux," "Pantomime," "Three Variations" (Gallop, Waltz, Danzón), and "Finale." It was premiered on January 14, 1945, by the Pittsburgh Symphony under Bernstein's own baton.

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