During his teenage years, he was involved in Labour Zionist youth movement Hashomer Hatzair, which was illegal in Morocco at the time.

Toledano debuted as a singer as a teenager, after sending demo tapes to the radio show "First Returns" ("תשואות ראשונות").

In 1970, his third album, Misty Garden, was released, and Toledano subsequently won the first Israeli Children's Song Festival, alongside the 10-year-old Irit Anavi.

Towards the end of the 1970s he toured Europe, and in 1978 released another solo album, La Boheme, singing the songs of Charles Aznavour.

Toledano subsequently composed the Israeli entry for the 1983 Eurovision Song Contest, "Chai", which was performed by Ofra Haza and also won second place.

In 1989, Toledano again competed in Kdam Eurovision, finishing in second place, and in 1991 he composed "Hava Nagila Discovered" for Uri Feynman's entry to the contest.

The couple has three children together, including Lehi Toledano, who participated in the 2020 edition of the Rising Star song contest.