Hyland was born in Woodhaven, Queens, New York City. He studied guitar and clarinet as a child, and sang in his church choir. When aged 14 he co-founded the harmony group the Delfis, which recorded a demo but failed to secure a recording contract. Hyland was eventually signed by Kapp Records as a solo artist, issuing his debut single, "Rosemary", in late 1959. The label employed the Brill Building songwriting duo of Lee Pockriss and Paul Vance to work with Hyland on the follow-up, "Four Little Heels (The Clickety Clack Song)", which was a minor hit, and the songwriting duo continued to work with Hyland.