The whole first side of the album consists of the composition "Dialogues for Jazz Combo and Orchestra", composed by Howard Brubeck and performed by the New York Philharmonic and the Dave Brubeck Quartet, under the direction of Leonard Bernstein.

The second side consists of arrangements of five songs from the musicals West Side Story and Wonderful Town, whose music was written by Bernstein.

The album started to take shape when "Dialogues for Jazz Combo and Orchestra" was premiered at a New York Philharmonic series on December 10, 11 and 13, 1959, with Leonard Bernstein conducting.

[3] This was considered at the time to be an early, successful jazz/classical crossover project – similar to those that had already been initiated by the Modern Jazz Quartet, Gunther Schuller and their peers in the study of what Schuller termed "Third Stream" music.

"In this work an attempt is made to construct a score giving the orchestra an important part to play which adheres strictly to written notes, while the particular combination, or 'combo', of jazz instruments, is free to improvise on the material of the movement..." —Howard Brubeck (Original LP liner notes) On the original vinyl LP record: The Dialogues for Jazz Combo and Orchestra was composed by Howard Brubeck; the other selections were composed by Leonard Bernstein.