 A native of Cambridge, Massachusetts, and son of the old-time minstrel, Milt G. Barlow (1843–1904), Barlow made his stage debut at the age of twelve in his father's minstrel troupe of "Barlow, Wilson, Primrose, and West".Barlow joined the 2nd (Special Service) Battalion of The Royal Canadian Regiment on October 22, 1899, for service in South Africa during the Second Boer War.According to newspaper and other accounts, he did also serve in the United States Army during the Spanish–American War and World War I, and eventually rose to the rank of full colonel in 1923.