He was born in Asaba, Delta State, to parents of mixed cultural backgrounds. He attended Asaba Government School at Asaba, the Sacred Heart School in Calabar and Hope Waddell Training Institute. He joined the labour force in 1930 as a customs officer working in Lagos, Port Harcourt and Calabar. He subsequently went to England to study Law during the 1940s. It was while studying that he started publishing poetic verses. He was then known as a newspaper poet, as most of his writings were published in the West African Pilot and a few other newspapers. In his writings, Osadebay used both his personal life and public events as inspiration.In Africa Sings, a collection of poems, he delved with themes from a personal point of view, such as a sullen poem written about his 25th birthday and the coming of middle age. However, his best work in the volume were poems written from an impersonal viewpoint. In his adventurous poem "black man troubles", he used pidgin English to lament the status of black Africans in colonial Africa and injustice in the society. His poems were also notable for faithfully representing modern poetic rhythm.