
Originally coming to Manhattan from Enid, Oklahoma to find his brother, he found that he liked the city. He created and owned the Stork Club which became the epitome of glamor. From the time of the speakeasy to the 1960s, he held court on East 53rd Street, desperately trying to please while often riding roughshod over all that he could intimidate. Surrounded by Jazz Age gangsters, he continually fought running battles against racketeers.
According to Ralph Blumenthlal in his 2000 book, Stork Club, another New York nightclub owner named Mary Louise Cecilia Guinan, widely known as "Texas," introduced Billingsley to her friend, the mass media commentator Walter Winchell in 1930. Winchell, with his outspoken wit, told it all. In his column in the Daily Mirror, he once called the Stork Club "New York's New Yorkiest place on W. 58th." The real entertainment at this club was the patrons themselves.
Billingsley offered a $25,000 reward for information leading to the return of his son-in-law in, Alexander I Rorke, Jr., in 1963, when his plane disappeared over the Caribbean.
Billingsley's mistress for a number of years was Ethel Merman.