It has a long recording history that includes numerous popular singers, has been heard on film, and is considered a standard for barbershop quartets.

James Thornton was a vaudevillian best-known during his life for his comedy monologues; however, he composed numerous popular songs, especially in 1880s and 1890s.

"[2] Bonnie Thornton, a popular vaudeville singer who sang many of her husband's compositions,[3] introduced the song in her act.

[citation needed] The 1947 revival of the song led to a number of artists recording it that year:[c] "When You Were Sweet Sixteen" is a standard of barbershop quartets.

[citation needed] This song also appears in the 1987 film Ironweed starring Jack Nicholson and Meryl Streep.

[citation needed] The song was sung in 2019 by the Steve Coogan character Martin Brennan in the comedy series This Time with Alan Partridge.