Cutugno was born in Fosdinovo, northern Tuscany.

He began his musical career as a drummer, but later formed a band that performed his own songs. He also had written for popular French-American singer Joe Dassin, contributing some of his most famous songs, including "L'été indien", "Et si tu n'existais pas" and Le Jardin du Luxembourg (written with Vito Pallavicini).

In 1976 Cutugno participated first time in San Remo Music Festival coming with his band Albatros in 3rd place. He then won in 1980 with the song "Solo noi" ("Only us", in Italian), and subsequently finished second in six editions: in 1984 with the song "Serenata" ("Serenade"), in 1987 with "Figli" ("Sons"), in 1988 with "Emozioni" ("Emotions"), in 1989 with the song "Le mamme" ("The Mamas"), in 1990 with Ray Charles with the song "Gli amori" ("Loves", but entitled "Good Love Gone Bad in Charles' version) and in 2005 with Annalisa Minetti with the song "Come noi nessuno al mondo" ("No One Else in the World Like Us). In total Cutugno participated in the festival 13 times.

He won Eurovision Song Contest in 1990 with his own composition "Insieme: 1992" ("Together: 1992"), a ballad which celebrated European political integration. Along with Gigliola Cinquetti, Italy's only other Eurovision winner from 1964, he presented the 1991 contest, which was staged in Rome as a consequence of his victory. However, when the scoring ended with a tie for first place the event descended into a degree of chaos, partly due to confusion over how the scoring system worked.