Henry Burr was born Harry McClaskey in Saint Stephen, New Brunswick, Canada, on 15 January, 1882. After his family moved to nearby Saint John, he started singing as a boy soprano in local churches and shows. He moved to New York in 1901, where he worked as a church soloist and met organist and singing teacher, Kate Stella Burr, whose name he used. He started recording in 1902, first for Columbia, but later for numerous other labels, including Edison and Victor. In 1906 he became a member of the Columbia Male Quartet. When the quartet moved to Victor, it changed its name to the Peerless Quartet and Burr took over its management on the death of its original manager in 1910. The group continued to be a highly popular recording and performing act until it disbanded in 1928. Meanwhile, in addition to performing with the Quartet, Burr continued to make recording under his own name and many pseudonyms for various labels. His recording career ended towards the end of the 1920s, when his style of singing sentimental singing went out of fashion. He died on 6 April, 1941.
Henry Burr recorded his version of Are You Lonesome To-night? on 5 August, 1927. It was released in October 1927 on a Victor 10" double-faced record (many Victor releases were single-sided), number 20873. The other side of the record contained a track by Vaughn De Leath, called Baby Your Mother (Like She Babied You).