After 6 years of classical studies and playing at nightclubs around Capri, Peppino and his group The Rockers released their first single, with the songs "Malattia" ("Sickness") and "Nun è Peccato" ("It's not a sin"), sung in Neapolitan in 1958.

After performing as the opening act for The Beatles in their 1965 tour of Italy, Peppino and his group attempted, with moderate success, to break out of the European market.

He won the prestigious Sanremo Music Festival in 1973, with the song "Un grande amore e niente più" ("A great love and nothing more").

The same year, he released the song "Champagne" that was a big hit in Italy, Germany, Spain and Brazil.

His novel Snow, taking place at the Turkish provincial town of Kars, includes the following passage: "Through the open door of a shop which sold women's stockings, bolts of cotton, coloured pencils, batteries and cassettes, he heard once again the strains of Peppino di Capri's "Roberta".