Brown was born in Chicago, Illinois to Oscar Brown Sr. and Helen (née Clark). Brown\'s father was an attorney and real estate broker. Brown\'s first acting debut was on the radio show Secret City at the age of 15. For high school, Brown attended Englewood Technical Prep Academy (then known as Englewood High School). After high school, Brown attended the University of Wisconsin–Madison, and Lincoln University but later dropped out. He also served a stint in the U.S. Army.\n', '

Brown\'s father had intended for him to follow in his footsteps and become a practicing lawyer. While he did help his father at his practice, he ventured off into other careers, such as advertising and serving in the army in the mid-1950s and writing songs. When Mahalia Jackson recorded one of his songs, "Brown Baby," he began to focus on a career as a songwriter. His first major contribution to a recorded work was a collaboration with Max Roach, We Insist!, which was an early record celebrating the black freedom movement in the United States. Columbia Records signed Brown as a solo artist, who was by now in his mid-thirties and married with five children.\n', '

In 1960, Brown released his first LP, Sin & Soul, recorded from June 20 to October 23, 1960. Printed on the cover of the album were personal reviews by well-known celebrities and jazz musicians of the time, including Steve Allen, Lorraine Hansberry, Nat Hentoff, Dorothy Killgallen, Max Roach and Nina Simone (Simone would later cover his "Work Song" and Steve Allen would later hire him for his Jazz Scene USA television program). The album is regarded as a "true classic" for openly tackling the experiences of African Americans with songs such as "Bid \'Em In" and "Afro Blue". Sin & Soul is also significant because Brown took several popular jazz instrumentals and combined them with self-penned lyrics on songs such as "Dat Dere", "Afro Blue" and "Work Song". This began a trend that would continue with several other major jazz vocalists. Several of the tracks from Sin & Soul were embraced by the 1960s Mod movement, such as "Humdrum Blues", "Work Song" and "Watermelon Man". Sin & Soul was followed by Between Heaven and Hell (1962). The success of Sin & Soul meant that much more money was spent on production and Quincy Jones and Ralph Burns were bought in to handle the arrangements.\n', '

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