Born in Agrigento, Cucchiara debuted in the late 1950s, mainly recording cover versions of American hits, before starting his career as singer-songwriter in 1962.

[2] In the following years he embraced folk music, first recording some classic pieces of the Sicilian tradition and then creating a musical duo with his wife Nelly Fioramonti, called Tony e Nelly, entirely devoted to the folk repertoire.

[1][2] While still mostly engaged in pop music, in 1971 Cucchiara got his best commercial hit with the song "Vola cuore mio", which peaked at number 11 on the Italian single chart.

[1][2] In 1973 his wife died from childbirth giving birth to the couple's second child, a boy.

[2] In later years Cucchiara focused his activity on stage, as author of other successful plays such as Pipino il Breve (1978) and La baronessa di Carini (1980).