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. They recorded "Arkansas Blues" and "Blue Blues". The record sold over a million copies. While playing in Atlantic City Red met Eddie Lang who joined the band and played with them 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. During the 1930s Red was often seen in New York's 52nd Street jazz club area. But, Red was musically inactive and moved back to his home town of St. Louis and worked in a brewery throughout most of the Depression. In 1944, he returned to New York and played with Eddie Condon and had one last recording date in 1947, before dying of cirrhosis of the liver.