[1] In the early 1950s he started his own jazz band, Fontana and his Trio, with piano, bass and drums, and around that time he met Leda, who became his wife and with whom they had four children: Luigi, Roberto, Andrea, and Paola.

[1] The same year, he made his debut as an actor, appearing in two musicarelli, which are movies heavily featuring musical numbers, titled Viale della canzone ("Avenue of song") and 008 Operazione ritmo ("008 Operation rhythm").

[3] At the 1968 Cantagiro summer festival, Fontana sang a cover version of the Tom Jones hit "Delilah", titled "La nostra favola".

[4] In 1971, the song "Che sarà", composed by Fontana with lyrics by Franco Migliacci, was performed by José Feliciano with the Ricchi e Poveri group at that year's Sanremo Music Festival, winning 2nd prize.

In 1982 his son Luigi wrote the first part of the music for a new song and this fact brought Jimmy back to compose and create again: he completed the song "Beguine" and sung it at 1982 Sanremo Music Festival, joining the 6th place; Luigi was on stage with his father in Sanremo and from that moment on they were performing together around Italy and abroad until Jimmy died.