When Stewart was 17 he went to Yonkers Raceway, and though underage, won $1000. With that money he went to Europe for the first time, visiting London, Edinburgh, Paris and Amsterdam.
He is a graduate of The American Academy of Dramatic Arts in New York. He later directed at the west coast branch of AADA.
Stewart is a member of The Actor's Studio Playwright's Unit and Director's Unit in Los Angeles.
Stewart supplemented his show business career by working in Yankee Stadium, leading to his memoir, My Life in Yankee Stadium; 40 Years as a Vendor and Other Tales of Growing Up Somewhat Sane in the Bronx.