Born in New York City, he began writing songs and vaudevilles after he graduated from high school.
An important event was his meeting with the composer Harry Von Tilzer in 1898—the two began a songwriting partnership thereafter, lasting almost 30 years.
Others that Sterling collaborated with include Arthur Lange,[1] Gus Edwards,[2] Bernie Grossman, M. K. Jerome, William Jerome, Frederick Allen Mills, his brother Raymond Sterling, Ray Henderson, Edward Moran and Bartley Costello.
He wrote the song America, Here's My Boy for the Peerless Quartet in 1917 in the aftermath of U.S. entry into World War I in April 1917.
[3] Other songs for which Sterling wrote the lyrics in whole or part include After the War is Over (1918) and When My Baby Smiles at Me (1920).