[9] There he was taught to sing Yiddish songs, but only began to learn the language much later, from a Chabad rabbi, after an acquaintance, Rudi Litwak, insisted that, instead of frequenting Milan's Central Synagogue, with its Italian rites, they visit a small synagogue, Beit Shlomo, at Porta Romana, an apartment used as a shul or shtibi where the language was being spoken passionately by elderly Holocaust survivors and that rabbi.

[d] Ovadia graduated in political science and made his debut in the theatre world under Roberto Leydi, as singer and musician in the band Almanacco Popolare.

In 1986, he produced Dalla sabbia dal tempo ("From sand, from time"),[13] staged in collaboration with his friend from his Jewish lyceum days, Mara Cantoni, with an accompanying orchestra that also plays a role in the spectacle.

[15][16] Throughout the 90s, Ovadia's performances drew rave reviews in Italy, and played a seminal role in the rise of a vogue for Jewish culture in that country.

[14] Around this time 1990-1991, he developed the idea of Golem, a cypher for Jewish diasporic identity, which crystallised in 1992 with his production of Oylem Goylem,[e] Based on H. Leivick's Yiddish play The Golem,[14] Ovadia's version, (Oylem Goylem is Yiddish for "The world is dumb"), skillfully melded satire and klezmer music sung by himself and deploys a range of accents: the Italian parts being recited by a Polish actor while Ovadia himself, when speaking Italian, pronounced it with a species of szmonces, a comic Yiddish accent used by Jewish actors in the interwar years when speaking Polish in cabaret performances.

In the same year, he produced Taibele e il suo demone and Diario ironico dall'esilio, written with Roberto Andò.

His following spectacles include Ballata di fine millennio (1996), Pallida madre, tenera sorella (1996), Il caso Kafka ("The Kafka File", 1997, with Andò), Trieste, ebrei e dintorni (1998), Mame, mamele, mamma, mamà... (1998), Joss Rakover si rivolge a Dio (1999), il banchiere errante (2001), L'armata a cavallo (2003).

In 2010 together with artists from nomadic cultures, such as the especially Roma and Sinti he performed a theatrical piece entitled Rom & Gagè after France took measures to expel its gypsy population.

[22] In 2016, in an event that was broadcast by RAI to an audience of millions, Ovadia was chosen to deliver one of the eulogies at Sforza Castle on the occasion of the funeral of Umberto Eco, Italy's most prominent post-war public intellectual and writer.

His characteristic woolen headdress is not a kippah,[j] but rather bears close similarities to those worn by Moroccans, a likeness which has often led to Arabs in the street greeting him as "one of them".

[30]In a learned article penned for Corriere della Sera in defence of Roberto Benigni's Life Is Beautiful, panned in some quarters as fabricating a version of the Holocaust and distorting its horror by introducing humour into its narrative of the tragedy, Ovadia documented the importance of the comical in Judaism and Jewish civilization generally.

[31] The American writer Ruth Gruber, while noting the seminal role Ovadia's work has played in promoting (especially Eastern European) Jewish culture, adds a reservation: Ovadia's performances, the image he projects and his immense influence in Italy illustrate another trap: the risk that Jews themselves can create or buy into or perpetuate Jewish worlds that are just as "virtual" or "absolutely fake" as those created by non-Jews.

[34] Though despised by intellectuals of the Haskalah, who used it satirically in plays to mock the "backwardness" of their traditional communities, Yiddish nonetheless became in turn, also through theatre, a "civilizing agency par excellence" for the Jewish masses under the stress of modernity.