Successful composer of the Golden Age of Brazilian song, Osvaldo Santiago had his songs recorded by some of the biggest names of the period.
In 1923, Santiago released his first book of poems, No Reino Azul das Estrelas. In the same year, he wrote his first lyrics, for a Nelson Ferreira song, presented by Laís Areda in a musical revue in Recife. In 1924, he founded the literary magazine Rua Nova, which would last until 1929. In 1926, with the success of his second book of poetry, Gritos do Meu Silêncio, moved to Rio de Janeiro, Brazil. His lyrics were first recorded in 1929 by Alda Verona ("Melodia de Aamor," with music by Nelson Ferreira) for her debut album. The song was included in the homonymous film by Lupe Velez. In 1930 he wrote the lyrics for "Hino a João Pessoa" with music by Eduardo Souto, which had enormous success as Francisco Alves' recording. Alvinho recorded "Bangalô" in 1931, for which Santiago wrote the music, giving Orestes Barbosa the opportunity to debut in the recording business as a lyricist.
At the same time, Santiago collaborated in the Carioca press, keeping a regular column in Barão de Itararé's O Malho. In 1935, Sílvio Caldas recorded his valse "Há um Segredo em Teus Cabelos" (with Gastão Lamounier) and Gastão Formenti recorded the march "Jóia Falsa." In 1938, he wrote a series of songs dedicated to launching the career of the then-novice Carlos Galhardo with Paulo Barbosa, like "Cortina de Veludo," "Italiana" (with José Maria de Abreu), "Madame Pompadour," "Lenda Árabe," "Torre de Marfim," and "Tapete Persa," among others. Taking daring liberties for those times, the songs renovated the romantic style. At the same time, the duo wrote Carnival hits like "Lig-Lig-Lé" (recorded by Castro Barbosa) and "Tirolesa" (recorded by Dircinha Batista in 1938). With Benedito Lacerda, Osvaldo Santiago wrote "Querido Adão" (a big Carnival hit in the Carmen Miranda recording) and the marcha junina "Pedro, Antônio e João," which was Dalva de Oliveira's opening album as solo singer. "Roleta da Vida" (with Muraro) was recorded by Carlos Galhardo. Other partners were Carolina Cardoso de Meneses, Gastão Lamounier, and Roberto Martins. Francisco Alves recorded his "Eu Não Posso Ver Mulher," a big hit of the Carnival of 1941. From the following year on, he became the biggest authority in the country on legal questions involving royalties, having published several books which were taken as references by the highest authorities on the subject.