[2] During Brown's twenties, he worked as the "world's first Black newscaster" for Negro Newsfront, a Chicago radio program that he coproduced with Vernon Jarrett.

[3] He worked briefly in real estate and public relations before running for political offices: for the Illinois Legislature in 1948 through the Progressive Party, and for the U. S. House of Representatives as a Republican in 1952.

[4] Brown was a contributor to the weekly WMAQ Chicago radio series Destination Freedom (written by Richard Durham) both during its early years (1948–1949) and in the 1950 revival.

At that time, Rush Street was totally segregated, and Sam and Shelly took him to Adolf's, an upscale Italian restaurant.

[2] 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"[7] for openly tackling the experiences of African Americans with songs such as "Bid 'Em In" and "Afro Blue".

Several of the tracks from Sin & Soul were embraced by the 1960s Mod movement, such as "Humdrum Blues",[8] "Work Song" and Herbie Hancock's, "Watermelon Man".

[1] 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.

Brown attempted to mount a major musical stage show in New York City called Kicks & Co. in 1961.

Kicks & Co. is set on an all-African-American college campus in the American South during the early days of attempted desegregation.

In 1962, he worked on the Westinghouse syndicated television program Jazz Scene USA, produced by Steve Allen.

[10] Brown sang the theme for the 1970 drama series Bird of the Iron Feather, the first all-Black television soap opera.

His son Oscar "BoBo" Brown III was a bassist and musical arranger who died in a car crash in August 1996.

"Somebody Buy Me a Drink", a track from Sin & Soul, was covered by David Johansen and the Harry Smiths on their eponymous first album.

Brown was scheduled to contribute lyrics to Allyson's 2006 album Footprints before his death; instead, she recorded his songs "A Tree and Me" and "But I Was Cool" as a tribute.