Jack Osterman: Broadway’s Bad Boy


Today is the birthday of Jack Osterman (1902-1939).

His mother had been an operetta star; his father a publicist and company manager. His first major show was Jerome Kern’s Oh, Boy (1917).

Billed as “Broadway’s Bad Boy” and “Broadway’s Playboy”, Osterman’s heyday as a vaudeville headliner and Broadway star peaked around the mid 1920s. A comedian/singer in the Jolson/ Cantor mode and for a time was mentioned in the same breath as they. He was also a songwriter.

His first appearance at the Palace was in 1924, He performed in the Century Roof revue A Night in Paris for almost the entire year of 1926. The following year he was in Artists and Models of 1927. Like many vaudevillians in 1929 he appeared in his own Vitaphone short, entitled Talking It Over.  

Osterman’s last Broadway show Smile at Me (1935) lasted only a couple of weeks. His career declined throughout 30s to the extent that in 1937  he took out a full page newspaper ad to remind everyone how significant he had recently been. In 1939 he died of of pneumonia. The eulogy was delivered by his best friend George Jessel.

I visited his final resting place at Woodlawn Cemetery in 2015 :

To find out more about vaudeville past and present, including stars like Jack Osterman consult No Applause, Just Throw Money: The Book That Made Vaudeville Famous.


    • Dear Ms. Iacomini, Maybe you can tell me if Jack Osterman is related to me, or, how I can find out. My father always said that he was his cousin, but I doubt that, because my grandfather was English, originally Dutch, but he came from a large family, so maybe. I would appreciate hearing from you. Thank you. Yours truly, Judith L. Osterman


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