He worked during the early 1950s bronzing baby shoes, as a trucker's assistant, and was also employed in a department store credit office and at a hosiery company. He graduated from New York University with a bachelor's degree in English Literature, and also earned his master's degree in English from Columbia University.
One of his early collaborators was Philip Springer, and a song they wrote together ("I Never Loved Him Anyhow") was recorded by Carmen McRae in 1956. Another song Ebb wrote with Springer was "Heartbroken" (1953), which was recorded by Judy Garland, the mother of his future protégée, Liza Minnelli. Other Springer-Ebb tunes include "Nevertheless I Never Lost the Blues". "Don't Forget", which he wrote with Norman Leyden, was recorded by singer Eddy Arnold in 1954.
On his first theatrical writing job, he co-wrote the lyrics for the musical revue Baker's Dozen in 1951. He wrote songs with Norman Martin for the Off-Broadway revue Put It in Writing (1962). He also worked with composer Paul Klein from the early 1950s onward, contributing songs to the cabaret revue Isn't America Fun (1959) and the Broadway revue From A to Z (1960), directed by Christopher Hewett.

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