Inside 1986, he met a successful producer-songwriter Giancarlo Bigazzi and played piano and intended for Umberto Tozzi and Raf. Around 1990 his solo career was launched when he won a newly talent subdivision of the San Remo Music Festival with "Disperato", written with Bigazzi & Beppe Dati, his common collaborators.

He experienced nifty profits through the Nineties around Italy also around Spain, Germany & France by using his albums Marco Masini, Malinconoia, ''T'innamorerai & Il cielo della Vergine''. Masini was occasionally criticised for the bleak & depressing subject matter of his songs; e.g., "Perché lo fai" (third place at San Remo Music Festival in 1991) was about white plague, & "Principessa" all about tyke abuse. Songs prefer "Bella stronza", & "Vaffanculo" were too controversial, stimulating condition by having a censors because of expressed language. Notwithstanding it was this equivalent raw, honorable, there are no-frills style that manufactured his songs outstanding hits sustaining his fans.

Masini returned to San Remo Music Festival in 2004, winning with "L'uomo volante", & within 2005 he class 3rd in the category "Man" by having "Nel mondo dei sogni".