Rossano Gentili was born in Florence on August 21, 1964, and plays keyboards and piano. In 1989 he and the bassist Stefano De Donato founded Dirotta su Cuba in the same city, and the singer Simona Bencini, born in Florence in 1969, joined them in 1990. Gentili's recorded career is the band's: Discogs lists no album under his own name, only his credits on Dirotta su Cuba releases, and on the records where it names his chair it gives him keyboards and voice, or piano.

The band's recording debut came in the summer of 1994 with the single "Gelosia," followed in 1995 by the album Dirotta su Cuba on CGD East West, which Italian Wikipedia reports as certified platinum. Five singles came from it in 1995, among them "Liberi di, liberi da" and "Solo baci," and Italian Wikipedia places them within the spread of acid jazz in Italy. Discogs tags the album Jazz-Funk. The second album, Nonostante tutto..., was recorded between November 15, 1995 and March 4, 1996 and released on June 7, 1996. Its guests include the guitarist Gigi Cifarelli, the trumpeter Demo Morselli and the singer Alex Baroni, Gentili is credited on keyboards and voice, and Discogs tags it Jazz-Funk, Soul and Acid Jazz.

In 1997 the band entered the Sanremo Festival with "È andata così," finishing twelfth, with the harmonica player Toots Thielemans accompanying them on the Ariston stage. An anthology of the same name followed, with a new version of the Delirium song "Jesahel." The fourth album, Dentro ad ogni attimo (September 12, 2000), carried the singles "Notti d'estate," "Bang!" and "In riva al mare" and credits Gentili on piano alongside several other keyboardists, a full horn section and a rotating cast of drummers. De Donato left after it. Fly followed in 2002 with Gentili again on piano, and Bencini departed soon afterwards.

In early 2004 Gentili and the singer Marquica founded the label Jazzet. Its first release was the 2005 album Jaz, which Discogs credits to Gentili as producer and executive producer, ten tracks including "L'iguana," "Genio della lampada" and "Amore normalissimo." Discogs lists four Jazzet releases, all of them Dirotta su Cuba: the album and singles drawn from it.

In 2007 De Donato returned to work with Gentili on funk reinterpretations of well-known Italian songs, which led to a tour. In 2009 Bencini rejoined and the original trio marked the twentieth anniversary with the Back to the Roots tour, closing at the Blue Note in Milan. The band reunited formally in 2012 and played the opening night of Estival Jazz in Lugano in 2014 and Umbria Jazz Winter in 2015 and 2016. Studio Sessions Vol. 1 (September 23, 2016, F&P Group and Warner Music Italy) re-recorded the debut album and added six new songs, with guest appearances by the trumpeter Fabrizio Bosso, the scat singer Gegè Telesforo, the singer Mario Biondi, the guitarist Riccardo Onori and the bassist Federico Malaman.

The group released its first English-language single, "Good Things," on January 18, 2019, and issued a thirtieth-anniversary edition of "Gelosia" on Warner in April 2024 with a remix by Tommy Vee. After a break that began in 2021, Bencini relaunched the band in 2023 with a new seven-piece line-up that does not include either founder. Gentili's activity since then is not documented in published sources.

Dirotta su Cuba sits where Italian pop, funk and jazz overlap, and the sources disagree on where to file it. English Wikipedia calls it a funk and pop jazz group, Italian Wikipedia lists funk, pop and jazz as its genres, and Discogs tags the first albums as jazz-funk and acid jazz, while AllMusic files the band under Italian pop. The band's most visible moments were pop ones: a platinum debut and a Sanremo entry. Its sound rests on a funk and soul rhythm section, horn arrangements and Bencini's lead voice, with mostly Italian-language songs.

Gentili's part in that sound is the keyboard chair and the production. He co-founded the group, played on its records for two decades, and produced the album that launched his own label. He has no recordings as a leader under his name, so this profile describes a bandleader and producer whose jazz side shows up in the groove-oriented arrangements, the festival bookings and the guests he has brought in, not in a catalogue of improvised leader dates.