A highly skilled guitarist with great musical sensitivity, inspired primarily by Robben Ford, Gentilini became part of the Pozzy Records scene in the late 1980s. In 1988, he recorded the demo tape Distance with Pozzy, which received strong critical feedback and marked the beginning of a collaboration that would evolve over the years.

After an initial break—during which Pozzy joined the band Travel alongside Nicolich, Gregory, and Gambino—Gentilini resumed an active collaboration with Pozzy throughout the 1990s, taking part in numerous live performances and recording projects. These include Distance Vol. 2 (2004), The Decision (2005), Pozzy in Rock (2007), and Running to the Door (2008).

In more recent years, he contributed to the album Living in Venice (2021) with the track I Know You Are and performed with his own band at Pozzy’s wedding in Venice. His latest appearance is on the 2025 track Best Friend, featured on Pozzy’s most recent album, Rebel, where he performs alongside F. Nicolich