Guccini moved to Pàvana during World War II, then returned to Modena where he spent his teenage years and established his musical career.

While his father served in the Italian military during World War II, Guccini lived with his grandparents in a small village in the Apennine Mountains in northern Tuscany called Pàvana, where he spent his childhood.

[3] His years spent in the somewhat archaic society of the mountains of Central Italy was to be a strong inspiration throughout his career, and it became one of the key recurring themes of his songs and books.

[6] Guccini spent his teenage years in Modena, as he later recounted in his second novel Vacca d'un Cane and in songs including "Piccola Città", which paints a bitter portrait of the city as "a strange enemy".

[12] The group included Pier Farri (drums), who would later become Guccini's producer; Victor Sogliani (saxophone), future member of Equipe 84; and Franco Fini Storchi (guitar).

[18] Record Producer CGD commissioned Guccini to write a song for the 1967 Sanremo Festival, "Una storia d'amore", to be sung by Caterina Caselli and Gigliola Cinquetti.

[24] In May 1967 Guccini made his first appearance in television, on Diamoci del tu, hosted by Caterina Caselli and Giorgio Gaber singing "Auschwitz".

In 1968 the 45 rpm record Un altro giorno è andato/Il bello was released; Guccini re-recorded the Side A song in an acoustic version for his 1970 album L'isola non-trovata.

The main themes of the album are the passage of time and the analysis of everyday life in the context of bourgeois hypocrisy,[28] with a noticeable influence from French music[29] and from Leopardi's poetic style.

[30] After this album Guccini started his 10-year-long collaboration with folksinger Deborah Kooperman, who played fingerstyle guitar on it, a style mostly unknown in Italy at the time.

[32] Guccini's fame began to spread beyond Bologna, partly thanks to the appearance in the TV show Speciale tre milioni, where he sang some of his songs and befriended Claudio Baglioni.

[4] Radici contains some of his most renowned and popular songs,[35] such as "Incontro", "Piccola Città", "Il vecchio e il bambino", "La Canzone della bambina portoghese", "Canzone dei dodici mesi", and "La locomotiva", based on a real event and dealing with themes of equality, social justice and freedom, with a style similar to the anarchic music of the end of the 19th century.

In 1973 Guccini released Opera buffa, a light-hearted and playful album, which showed his skills as an ironic, theatrical and cultured cabaret artist.

[41] It included six long and melancholic songs, a mirror of the crisis Guccini faced, worsened by constant disagreements with his producer Pier Farri.

[47] The first album released by Guccini in the eighties was Metropolis, which was characterised by the description of cities with a symbolic value: Byzantium, Venice, Bologna and Milan.

[61] In 1981 Guccini was the co-author, along with Giorgio Gaber, Sandro Luporini and Gian Piero Alloisio, of the musical Gli ultimi viaggi di Gulliver.

It included live versions of many of his popular songs, recorded mainly at a concert held in Piazza Maggiore in Bologna, in which several guests performed alongside Guccini: Giorgio Gaber, Paolo Conte, I Nomadi, Roberto Vecchioni, and Equipe 84.

Several of the songs portray people from Guccini's life: "Van Loon" is his father, "Culodritto" is his daughter Teresa, and "Signora Bovary" is himself.

[71] The literary critic Paolo Jachia commented: "Guccini's enormous poetic and cultural effort has been opening the best tradition of Italian poetry to Dylan-esque ballads.

[82] In the same year, lyrics from "Canzone per Piero" were included in a final upper secondary school exam";[83][84] Guccini claimed he was "embarrassed and glad" about being alongside Cicero and Raphael.

[89] Luciano Ligabue, friend and colleague of Guccini, entitled him a song, "Caro il mio Francesco" on his album Arrivederci, mostro!.

In the article about the discovery on the botanical magazine Piante Grasse, Donati explained that he discovered the unknown plant whilst listening to Guccini's "Incontro", adding, "I could not have named it after anyone else.

Throughout his lengthy career, some defining characteristics stand out in his work, such as the use of different registers, the literary references to several writers, and the use of a variety of themes to reach moral conclusions.

In "La primavera di Praga", he expressed criticism of the Sovietic occupation of Czechoslovakia in 1968 , and "Piccola storia ignobile" supported the Italian abortion law.

"Piazza Alimonda" was about the riots at the G8 summit in Genoa and "La locomotiva" was about the anarchic Pietro Rigosi running a locomotive at full steam towards death.

Guccini recounts stories he heard from elderly people living on the Tuscan Apennines; critics praised the "philological accuracy" of the book.

Vacca d'un cane depicts a teenage Guccini in Modena, as he realizes that the city's provincialism will be an obstacle to his intellectual growth,[104] while Cittanòva Blues the last part of his trio of autobiographical books, tells of his time in Bologna, seen as a "little Paris".

[105][106] Guccini also collaborated with Loriano Macchiavelli for a series of Noir books, and published a Dictionary of the dialect of Pàvana which showed his ability as dialectologist and translator.

[109][110] Guccini's first experience as actor was in the 1976 movie Fantasia, ma non troppo, per violino, directed by Gianfranco Mingozzi, in which he played Giulio Cesare Croce, a poet who narrates the history of Bologna.

[114] In the 2000s he acted in three movies directed by Leonardo Pieraccioni, Ti amo in tutte le lingue del mondo (2005),[115] Una moglie bellissima (2007)[116] and Io & Marilyn (2009).