He was a comedian and singer who rose to fame back in the 1930s, known not only for his talent but also for his close connection to notorious gangster Al Capone. His life story was so compelling that Frank Sinatra portrayed him in the 1957 biographical film The Joker Is Wild, which brought his journey to a wider audience. Before he became well-known, he made a bold move that almost ended in tragedy—he turned down Al Capone’s demand to perform at the Green Mill Cocktail Lounge, a decision that put his life in serious danger. Despite the risks, he stood his ground, showing the kind of courage that defined much of his character. In 1946, he tied the knot with actress Martha Stewart, adding a personal chapter to his public persona. However, their marriage didn’t last, and they went their separate ways just two years later. Throughout it all, his legacy as a performer with ties to one of America’s most infamous figures kept his name alive in pop culture history.
Al Capone, along with his rivals in the underworld, really wanted him to perform at their clubs. It seemed like everyone was after him—both Al Capone and the competing gangsters saw value in having him play for their crowds. Whether it was Al Capone’s influence or the pull of rival bosses, the demand was clear: they all wanted him on stage at their venues. In fact, Al Capone went to great lengths to secure his talent, just as the other crime figures did. Ultimately, both Al Capone and the opposing gangs recognized his appeal and were eager to have him play in their clubs.