[1] His mother, Anna Maria, sang and played piano, and was an elementary school teacher before she quit the profession to have a life at home with the family.

In his early years of his career he met the record producer Giancarlo Bigazzi who introduced the young musician to the music business, as a collaborator with artists like Raf and Umberto Tozzi.

Eventually, in 1990 he participated in the 40th edition of popular Sanremo Festival with one of his signature songs, Disperato, and won first prize as new artist of the year.

After winning third place, now among the main competitors, in the 1991 edition of Sanremo Festival with Perché lo fai (a controversial song about an addicted young woman), Masini, now an emerging star, released his second album, Malinconoia (a composite word coined by the artist indicating a mixture of melancholy and boredom, in Italian malinconia and noia), that became a big hit in the Italian charts, despite the somber mood of most of the record.

The title track was presented during the popular summer music competition Festivalbar in the long playing records category, and was awarded first prize.

In an interview for the newspaper Corriere della Sera, Masini claimed that the v-word was dedicated to "the liars and who call me 'prophet of the depression'"[2] and the song contained also some harsh verses directed to the record labels and their policies.

After nearly four years of silence, on 12 November 1998, the Scimmie ("Monkeys") album was released by Ma label, founded by himself, Mario Manzani and Marco Poggione.

With Scimmie, Marco said he wanted to recover the music from the 1970s that he loved and was back in fashion: the views of the critics were strangely positive, but not public opinion, which decreed the album's commercial failure.