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LeRoy Neiman had a long personal relationship with Frank Sinatra, one of the greatest singers and entertainers of the 20th Century. The artist portrayed the Chairman of the Board many times, from quick pencil sketches at live performances to full-color oil paintings. Neiman, always drawn to action, usually depicted Sinatra singing on stage and at recording sessions. The new portrait, unlike all the previous ones, shows Old Blue Eyes quietly sitting still. Captured in shades of aqua and blue, he is at a recording session, appearing typically casual, sitting backwards in a chair and wearing his trademark hat. But while he may look relaxed, he is actually listening intently to a playback of his own singing, judging his voice and performance. Sinatra was a perfectionist and his own harshest critic, and would not accept a "take" until he thought it was perfect.
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