Will Oakland (January 15, 1880 – May 15, 1956) was an American countertenor famed for his exceptionally high vocal range.
Oakland began his musical career after leaving the United States Army in 1905, joining Lew Dockstader's minstrels in Rochester, New York.
In addition to appearing as a solo performer, Oakland recorded duets with Billy Murray, sometimes singing the female part in love songs.
He often sang woeful, sentimental songs that contrasted with Murray's usually upbeat repertoire.
From 1912 to 1914 Oakland recorded in the Heidelberg Quintet, joining the members of the American Quartet.