mcleod's began his career by working with slim bassett. during the 1930s they traveled regularly with mcleod popularizing his own songs by performing them on radio stations throughout the southern united states. the duo landed a regular show in new orleans in 1935, known as "mac & slim." he continued to work with bassett until he married his wife addie. he continued his career as a radio entertainer alongside his wife addie on wjjd in chicago. "mac and little addie",as they were known, played for the station's supper time frolic show until the start of world war ii. during the war, mcleod worked in a factory in michigan. he continued to write songs during the war and resumed his career at wlac in nashville, tennessee once the war had ended. he was with the station until 1957, appearing both solo and as mac and little addie.