After he took up residence in the lounge of New York's elegant Hotel Carlyle in the late 1960s, vocalist and pianist Bobby Short became an icon of New York and American cultural life. Short called himself a saloon singer, but actually he roosted at the top of the hierarchy of entertainers who perform in cocktail lounges, and indeed he did much to define the modern categories of lounge singer and cabaret singer. New York visitors stopped in at the Café Carlyle for decades to hear Bobby Short, to glimpse the lifestyles of the city's well-heeled residents, and to take a tour through the classics of American popular song with one of its most knowledgeable curators for a guide.
Robert Waltrip Short, the ninth of ten children, was born in the small town Danville, Illinois, on September 15, 1924. His father was a coal miner from Kentucky, who sometimes landed higher-paying jobs, and the family had a piano and a radio tuned to jazz. At age four, Short taught himself to play the piano. The resourcefulness that put Short on the road to performing in posh nightclubs was inherited in part from his mother. The young musician had a childhood remarkably free of racial discrimination.
. When he was nine, Short began to supplement the household's income by playing and singing in taverns. His skills developed quickly, and he turned into something of a teenage sensation. Agents who heard of his talent booked him into clubs and hotels in Chicago and New York. Short developed a taste for fine clothes, and later in life he would frequently appear on lists of best-dressed men. But his father's death in 1936 interrupted his high-flying career; he went back to Illinois to be with his family . Short launched his adult career in 1942, performing at Chicago's Capitol Lounge. His reputation spread, and he landed nightclub slots in other large cities. Sometimes he shared a bill with singer Nat King Cole, a friend who influenced his expressive vocal style. By 1948, Short was a regular at the Cafe Gala in Los Angeles, staying there for three years and leaving only when he felt that he had become stuck in a velvet-lined rut.