Red was the leader of the Mound City Blue Blowers, in which he played comb, kazoo, and sang. Later, he went on to play with the Paul Whiteman Orchestra. While working as a bellhop in St. Louis he and some friends would get together and play on the street and he was "discovered" and taken to Chicago to record in 1924. The sensational novelty group, Red, Eddie Lang, Jack Bland and Dick Slevin had a million seller for Brunswick in"Arkansas Blues". This gave them an opportunity to perform in London, After his return to America, Red became active as a Jazz Promoter, more than as a Jazz musician. Red worked as a talent scout and set up the first Okeh Recording date for Beiderbecke, Eddie Lang and Frankie Trumbauer which featured the famous recording "Singing the Blues". In 1927, he promoted a Paramount Recording session at which a group of Chicagoans recorded the "Friar's Point Shuffle". In 1928, Okeh Records cut four sides with his group called McKenzie and Condon's Chicagoans.
In 1930 he recorded with a number of famous musician, Fats Waller, Coleman Hawkins, Benny Goodman, Bud Freeman. Eddie Condon and Josh Billings. He recorded Arkansas Blues again. Red was the equal of Jack Teagarden as a white jazz singer, of which there were only a few.
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