Dilermando Pinheiro's biggest hits as interpreter were "Seu Libório" (João de Barro/Alberto Ribeiro) and "Risoleta" (Raul Marques/Moacir Bernardino). With Ciro Monteiro, he kept the Dupla Onze at the Rádio Mayrink Veiga, having hits with "Florisbela" (Nássara/Frazão), "Formosa" (Baden Powell/Vinícius de Moraes) ,and "Até Amanhã" (Noel Rosa).
At 13, he started to play the pandeiro at the Military Police band. His later trademark was copied from the friend Luís Barbosa, the hammering on a straw hat while singing. In 1936, he debuted at Rádio Guanabara, followed by Tupi and Nacional. In 1939, he formed the Dupla Onze with Ciro Monteiro and performed at the Rádio Mayrink Veiga. Their first album came in 1956, Sambas Do Passado. Ostracized until 1965, in that year it was brought again to the artistic scene in a show staged by Sérgio Cabral and shared with the old partner Ciro Monteiro, Telecoteco Opus No. 1, which was also released as a record. He recorded an LP with trombonist Raul de Barros and seven other albums.