Avoiding his father, who had discovered the boy's place of refuge, he rode a freight train to Kansas City, Missouri.

[1] Howard toured in a stock company production of "Little Eva," [2] then performed in vaudeville as a boy soprano at the age of 11.

They played the Midwestern vaudeville circuit, drawing notice enough in Chicago to obtain an engagement in New York at Tony Pastor's Music Hall on 14th Street, where they were a big hit in 1898.

[3] Howard produced a string of pop jazz hits, including "What's the Use of Dreaming?," "I Don't Like Your Family," and "A Boy's Best Friend Is His Mother".

In 1939, Howard collaborated with Beatrice Kay, a husky-voiced showgirl, on a radio program called The Gay Nineties Revue,[4] which revisited his hits from the turn of the century and the teens, which by then had become nostalgic American entertainment for listeners during the Big Band Era.

In 1947, a motion picture was produced based on Howard's biography called I Wonder Who's Kissing Her Now, starring Mark Stevens, with Buddy Clark taking on the singing chores.

The film generated legal controversy when Harold Orlob, a former employee sued, proved his authorship of the composition, and won the right to remove Howard's name from the song.