Jaime Redondo had his biggest hit as a composer with "Ave Maria" (written with Vicente Paiva), recorded by Dalva de Oliveira in 1950, while Francisco Alves also had success with his version of "Que Noite!... E Que Pequena" (J.L. Sanders). His successes as an interpreter are "Alguns Dias Bons" (N. Shilkret/L. Pollack, 1929), "Ao Cair do Pano" (Sherman/Lewis, version by Redondo, 1929), "Comendo Bola" (Hekel Tavares/Luís Peixoto, 1929), "Harmonia! Harmonia" (Hekel Tavares/Luís Peixoto, 1929), "Ilusão Que Se Vai" (Jaime Redondo, 1929), "Jaci" (Jaime Redondo, 1929), "Mas Que Trapaiada" (Jaime Redondo, 1929), "Meu Pintassilgo" (Jaime Redondo, 1929), "Mulata" (public domain, 1929), and "Saudades" (Jaime Redondo, 1929). In the cinema, Redondo worked either as an actor or producer, photographer, director, and scriptwriter in films like Coisas Nossas (Wallace Downey, 1931) and A Voz do Carnaval (Adhemar Gonzaga/Humberto Mauro, 1933).
Redondo started his artistic career as a singer at the Rádio Educadora Paulista, the first radio station of São Paulo, founded in 1923, of which he was the director of popular music. He also pioneered as a Columbia artist, recording his first album in 1929, the song "Beijos e Beijinhos." Through 1931, there he recorded 27 albums with 50 songs. His composition "Saudade" was his second recording and first success. He also had hits with the valse "Ao Cair do Pano," his version of the Sherman/Lewis composition, and with his song "A História de Jaci" (1930). Abandoning the career of a singer, Redondo became the artistic director of the Cassino da Urca. His songs were recorded also by João Gilberto, Maria Bethânia, Helena Pinto de Carvalho, Maestro Gaó, Arnaldo Pescuma, Irmãs Pagãs, Paulo Tapajós, Dalva de Oliveira, Rubens Leite, Poly, Orquestra Cassino de Sevilha, Alberto Ribeiro, Lana Bittencourt, and others.