Later De Gregori formed a band with his friends Antonello Venditti, Mimmo Locasciulli and Giorgio Lo Cascio, who all had success as singer-songwriters in the following years.

The 1974 album Francesco De Gregori (also known as the "Sheep" due to the unusual cover by Gordon Fagetter) showed even more experimental and sometimes obscure lyrics, and again was a failure.

Bufalo Bill (1976) confirmed De Gregori's qualities, and contained at least two classics: the eponymous song and "Santa Lucia", the singer's own favourite.

However, during a concert held in Milan in 1976, De Gregori, who had always declared his inclination to left-wing ideas and ideals, was fiercely contested by a group of extreme left agitators.

The following year he joined his old friend Lucio Dalla with a highly successful live tour, entitled Banana Republic, and published a studio LP, Viva l'Italia featuring American musicians.

The ballad "San Lorenzo", with a rare piano performance by De Gregori, concerns the dramatic episode of the bombing during World War II of the quarter in Rome by Allied planes.

Il fischio del vapore ("The Whistle of the Steam", 2002) was a collaboration with the folksinger Giovanna Marini, who had already worked with De Gregori in a song for Titanic.

A biography of Francesco De Gregori, "Quello che non so, lo so cantare" ("What I Don't Know, I Know How to Sing"), edited by Enrico Deregibus, was published by Giunti in 2003.

As well as the celebrated track "Diamante" ("Diamond"), this contained pieces written for Zucchero and included on his album Oro incenso e birra ("Gold, Incense and Beer"), a demo of "Mannaggia alla musica" ("Damn to the Music") from 1979, originally written for Ron and previously presented on the live album Bootleg, and the B-side of the single "Viva l'Italia" ("Long Live Italy"), the celebrated "Banana Republic", sung without Lucio Dalla.

2010 opens with the news (given on 2 January) of a new set of concerts with De Gregori and Lucio Dalla, over thirty years since the splendor of Banana Republic, at the Vox Club Nonantola, with the name "Work in progress".

On 22 March 2010, Dalla and De Gregori lead the new TV show on Rai 2, entitled Due, during which they perform individually and in duets, covers and songs from their repertoires.