He was the writer of "You Go to My Head", "Honey", "By the Sycamore Tree", "That Lucky Old Sun", "Breezin' Along With The Breeze", "Right or Wrong," "Beautiful Love", "Drifting and Dreaming", and "Louisiana Fairy Tale" (Fats Waller's recording of which was used as the first theme song in the PBS Production of This Old House),[1] each song in collaboration with other people such as Beasley Smith, Ervin R. Schmidt, Richard A. Whiting, Wayne King, and Loyal Curtis.
Gillespie soon landed a job as a typesetter for the Cincinnati Times-Star, ultimately maintaining his membership in the International Typographic Union until his death.
He found work as a "plug" man, entertaining audiences at local vaudeville shows by playing and singing songs he had written.
His first break came in 1911 when he met Roy Steventon, performing with Mildred Lovejoy in a dancing act at the Keith Theater in Cincinnati.
Haven was paid one and a half cents for each piece of sheet music sold, total royalties which amounted to only a few dollars over the next several years.
He first gained notice in 1925 with "Breezin Along With The Breeze", in collaboration with Egbert Van Alstyne, Ervin R. Schmidt, and Loyal Curtis, which was recorded by Josephine Baker among many others.