As a youth, he earned pocket money by working in the general store and operating a dance hall with friends that, on one occasion, featured a young Guy Lombardo conducting the orchestra.
He attracted Steamtown, USA, a Hilton Hotels & Resorts (for which grand opening McNulty hired Guy Lombardo’s orchestra to play) and the Montage Ski Resort to Scranton, Pennsylvania, which is on a thoroughfare that “Jimmy” stated a million Canadians passed down on their way to gamble in Atlantic City, New Jersey.
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After the war he was part of Tin Pan Alley, writing a multitude of songs that were performed by such artists as Sarah Vaughan, Frank Sinatra, Billy Eckstine, Harry James, Guy Lombardo, Sammy Kaye, Xavier Cugat and Jimmy Heath.
He based his style of music on that of fellow band leader Guy Lombardo, and by the 1930s Winnick was performing regularly in several prestigious London venues including the Hammersmith Palais de Danse, the Carlton Hotel, and the San Marco Restaurant, with singer Sam Costa.
This six-sided record set offers surprisingly accurate imitations of then-popular bands and singers, including lampoons of his former employees Goodman, Dorsey, and Shaw, as well as Guy Lombardo, Larry Clinton, Ted Lewis, Count Basie, and other "name" bandleaders.
Spillville is also the site of the Inwood Ballroom, established in 1920 and the destination of several popular 20th century musicians such as Louis Armstrong, Glenn Miller, Guy Lombardo and The Byrds.
Patrons of the Val Air could dance under a canopy of stars to the melodious sounds of Guy Lombardo, Benny Goodman, Glenn Miller, and other big bands.
After retiring in 1978, a year after Guy Lombardo died, Kenny settled in Plandome, New York.