Using various aliases, Harry sang and released for essentially every single recording company in existence in the first twenty years of the 20th century. Though he had recording contracts with many of them, none were exclusive until July of 1920 (first publicly announced in Talking Machine World in November of 1920) when he signed an exclusive contract with Victor, using the Henry Burr alias. However, many companies still were in possession of recordings made previously, thus there still did occur new non-Victor Burr releases after 1920.
An extremely successful tenor in the 1900's, 1910's and early 1920's, Harry's popularity waned in the mid 1920's. In 1925, he began performing on radio on the Goodrich Zippers radio program, then turned to production, rather than performance beginning in 1927 - 1929 when he produced the Cities Service Hour program. In 1928, he formed Henry Burr Inc. as a production company handling many of the national commercial radio shows of the late 1920's. On November 25, 1929, Harry was appointed as director of the Artist's Bureau for the Columbia Broadcasting Company, then newly formed. In the 1930's, he did not record, working instead as a radio and recording producer. His performance career revived in the mid 1930s, singing as "The Dean of Ballad Singers" on the WLS National Barn Dance Troupe show, recorded in Chicago and broadcast nationally on CBS, and continuing through the end of February, 1941.
He had no children of his own, only an adopted stepdaughter, child of Cecilia Niles and her first husband. The stepdaughter's name was Marguarite. Marguarite died in the late 1930's.
He died in Chicago from cancer.