Frank Sinatra

Frank Sinatra

Turns out ol' blue eyes wasn't just a romantic crooner. Apparently, the famous Rat Packer also used his penchant for painting to woo companions such as his second wife Ava Gardner. In 1950, the early days of his affair with the actress, Sinatra gifted her with the pup portrait pictured here. Though he was always very private about his artistic undertaking, it is known that in his later years, throughout the 90s, his traditional take on painting gave way to abstract expressionism in the style of Mark Rothko.

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