In 1919, Flemming was out of uniform and back in New York City for further studies, taking trombone, cello, and music theory at Frank Damrosch's Conservatory. Near the end of 1921, he made his debut as a trombonist on record with bandleader Johnny Dunn. Prior to his next European trip, this time at the behest of noted expatriate bandleader Sam Wooding, Flemming and partner Bobby Lee fronted a band in Philadelphia. Until 1927, Flemming toured all over Europe with Wooding and even did some gigs in South America. Flemming continued playing with Wooding stateside for a brief period, then became part of Lew Leslie's Blackbirds revue. By the end of the '20s, this show had provided an opportunity for more international touring, including popular appearances in London and Paris.
The trombonist stayed in Europe and launched his own band in 1930, the International Rhythm Aces, but also continued working with Wooding. He joined the latter leader in Berlin yet was soon off on his own again, backing up the great performer Josephine Baker and taking his combo to Buenos Aires. Flemming traveled as if trying to make the normal musician seem like a homebody. Based out of Paris in 1933, he took his group to India for a Calcutta hotel stint that lasted half-a-year. The group also gigged in Shanghai and Ceylon. The mid-'30s brought an opportunity to work with Sestto Carlin's Society Orchestra in Italy and a chance to try his lot as a vocalist at a club in Berlin. Flemming was also employed as an interpreter for the American Olympic team during this time.
Pianist Earl Hines finally provided a reason to return to the United States with an offer to work in his terrific band at the Grand Terrace venue; however, the trombonist's union card wasn't in order and he was not allowed to blow. He wandered off to Cicero, IL and began singing there, then joined up with Fats Waller for an engagement that started on the final night of 1940 and continued until 1942. With Waller, Flemming sang as well as played trombone. The subsequent step in his wanderings took him to California and although he continued doing many music gigs, he took a day job as a tax inspector. This new home base allowed him a chance to poke his nose into the Hollywood film world; Flemming can be seen onscreen in both #Pillow to Post and #No Time for Romance.
Flemming took a vacation to New York City in 1949 and wound up staying. There was enough work offered to him for a return to full-time music, tallying in the freelance opportunities plus a regular job with the fine trumpeter Henry Red Allen which ran from 1953 through 1958. Come the far-out year of 1964, Flemming had moved on again, this time to Spain for a 16-month engagement in Madrid. He also had residencies in Torremolinos and Malaga and made some of his final recordings in Berlin alongside fellow veterans such as Albert Nicholas and Walter Bishop, Sr.. Despite all his efforts to wind up somewhere quite different then where he started out, Flemming passed away in New York City. ~ Eugene Chadbourne, Rovi