His career began in 1977 with his breakthrough hit,[3] "Shir Prida" ("Farewell Song"), written by Shlomo Artzi, and has produced multiple hit songs across several decades, which also include "Im Ata Basviva" ("If You Happen to Be Around"), "Derekh HaKurkar" ("The Eolianite Road"), and "Makhur" ("Addicted").

[4][1] Sinai has gained significant success in Israel during the 1980s,[1] and has subsequently released three additional studio albums in 1992, 2003, and 2011.

[3] In 2011 Sinai announced via Facebook that he was effectively retiring from making new music for what he perceived as a lack of respect for the older generation of musicians,[5] but has released multiple singles of new material since then.

Sinai competed in HaKokhav HaBa for the right to represent Israel in the Eurovision Song Contest 2024, which gained much attention in Israel since most of the show's contestants are usually at the beginning of their careers;[6][7] he made it to the top 14 round of the competition, being eliminated on 25 January 2024.

Sinai also participated in the previous Israeli selection Kdam Eurovision in 1985 and 1987, and finished 4th and 8th, respectively.