Singh next reteamed with the Akhtars on "Gully Boy" (2019), a musical inspired by the life of the street rappers Divine and Naezy. Singh found little in common with his character of a poor man who aspires to become a rapper, and in preparation he underwent acting workshops and spent time with both Divine and Naezy. He performed his own rap songs and was pleased that the film brought attention to India's underground music scene. The film premiered at the 69th Berlin International Film Festival. Deborah Young of "The Hollywood Reporter" commended him for displaying a "pleasingly full emotional range that extends to drama and hip-hop" and writing for Film Companion, Baradwaj Rangan praised his ghetto accent and found his understated performance to be a "superb showreel for his range". "Gully Boy" won a record 13 Filmfare Awards, and Singh received another Best Actor award.