Norman Rockwell, the renowned painter and illustrator best known for the popular covers of American culture he created for New York’s The Saturday Evening Post, was again the talk of the town when one of his works – Sinatra: An American Classic – was the most sought-after lot at Sotheby’s Lady Blue Eyes: The Property of Barbara and Frank Sinatra auction. When the gavel finally dropped on his 1973 oil canvas painting of the beloved singer, actor and hell-raiser, the winning bid – after a heated six-way battle – was US$687,000, nearly six times its US$120,000 reserve price.

Initially published in conjunction with an article of the same title (a work by his long-term friend and collaborator, Rosalind Russell) in a 1973 edition of the Ladies Home Journal, the original Frank Sinatra portrait spans 47.6cm x 33cm and was one of the last paintings Rockwell completed before his death in 1978. As well as the many years he spent working as a magazine illustrator, Rockwell was also known for his portraits of notable American celebrities and politicians, including John F Kennedy, John Wayne and Ronald Reagan. What makes the Frank Sinatra portrait so unique, though, is its vibrant green background, as most of Rockwell’s works were predominantly grey. Maybe Frank insisted he did it his way.