After leaving school, he became an arranger for such big bands as those of Stan Kenton, Vincent Lopez, and Johnny Richards.

[1] Weiss contributed to a number of film scores: Murder, Inc. (1960), Gidget Goes to Rome (1963), Mediterranean Holiday (1964), and Mademoiselle (1966).

The Broadway production starred Sammy Davis Jr. First Impressions was based on Jane Austen's Pride and Prejudice.

It was set in New York during the American Civil War, and the Broadway production starred Shirley Jones and Jack Cassidy.

Weiss wrote the lyrics for the jazz standard "Lullaby of Birdland", which became a hit for Ella Fitzgerald.