While still in high school, Caravello began playing with a string of bands mostly performing covers of Top 40 songs. As he described it later, "Top-40 in those days was everything – funk, ballads, rock, country, and everything. It was a great time for radio." His first band, The Cellarmen, was formed in 1965 by him and several of his friends. They started playing local clubs in Brooklyn and Queens. Only a handful of recordings were released on the Jody Records label, a small Brooklyn recording studio. Caravello then joined a band called "Things That Go Bump in the Night" and later "Smack", the latter of which consisted mostly of members from The Cellarmen, who disbanded in 1968.