In 1968, he graduated in Classical Literature at the Catholic University of Milan, where he subsequently worked for two years as assistant lecturer of History of Religion.

Vecchioni's breakthrough happened in 1977 with Samarcanda, an album where he drew inspiration mostly from autobiographical themes, intermingled with dreamy, literary, historical and mythological references.

Vecchioni's skills were confirmed in the following works, Calabuig, Stranamore e altri incidenti (1978), where the literary citations predominated, and in Robinson (1979), where instead the autobiographical inspiration prevails.

The songs "Signor giudice" and "Lettera da Marsala" of the latter work deal with the problems Vecchioni had had in the preceding years: respectively, a charge for marijuana possession (from which he was acquitted) and a dispute with his former record label.

On 19 February 2011, he won the 61st Sanremo Music Festival[2] and the "Mia Martini" Critics' Award[3] with the song "Chiamami ancora amore" ("Call me Love again").