Rossi calls himself a provocautore (an Italian portmanteau for "provoking author") as throughout his career he has been regularly criticized over his choice of lifestyle and the lyrics in his songs.

It was his mother herself who decided to enroll him in singing school when he was a little boy, a choice that must have seemed rather peculiar within the mentality of a small village in the Apennines like Zocca.

Encouraged by his friend Gaetano Curreri (now leading member of Italian rock band Stadio), Rossi released his first EP on 13 June 1977, which included the songs "Jenny è pazza" (Jenny is crazy) and "Silvia", and a full-length album in 1978, Ma cosa vuoi che sia una canzone ("What do you expect from a song").

His most controversial album, Colpa d'Alfredo ("Alfredo's fault") followed in 1980; its title track was censored from the radio and let loose bitter criticism because it contained some lyrics referring to women considered too explicit at that time.

Rossi argued that Salvalaggio evidently did not understand his music and remarked how easy it is to criticize a still unknown artist who cannot defend himself.

In 1982, Rossi took part for the first time in the Sanremo Music Festival, performing the song "Vado al massimo" ("I'm taking it to the max").

The following year, he reappeared at the Sanremo Music Festival, this time performing "Vita spericolata" (Daredevil Life), probably his most popular song, and finishing in second-to-last place due to his apparent state of intoxication.

The title track, whose lyrics are about Coke (but also demonstrate a clear assonance with cocaine), won the Festivalbar '83, and his tour that year was an enormous success.

In 1987 Vasco Rossi's ninth album, C'è chi dice no ("There Are Some Who Say No"), was released; the ever-increasing numbers of fans showing up to his concerts forced him to quit performing in clubs and normal-sized venues and begin the era of something for which he is known to this day—playing in and selling out big arenas and stadiums.

Rossi invited a few Bosnian bands like Sikter, Lezi Majmune, and Protest to perform but was heavily criticized by the press because the proceeds weren't given to charity, despite the fact they were never meant to be.

The drum of the song "Anche se" ("Even If") later called "Praticamente perfetto" ("Practically Perfect") was recorded by Taylor Hawkins.

In 2002 Rossi released his first official recording of remastered songs in their original version, Tracks, which was followed by three sold-out performances at San Siro Stadium in Milan.

In December 2005 he returned to his home town of Zocca, where his childhood friends and the rest of the community organized a tribute in his honor, including a photo display and other celebrations.

On 4 May 2010, the newspaper Corriere della Sera reported Vasco Rossi as saying the American and British governments had been responsible for preventing him and other Italian musicians from becoming known in those countries.

During the recording session for the new album, Vasco wrote the lyrics to a song musically written by Dave Grohl, entitled "Sognare ancora" (Dreaming Again).