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This charcoal-on-board portrait was done by artist Robert Stephen Simon. It depicts Frank Sinatra in a pose from his 1965 classic movie, "Von Ryan's Express," wearing a bomber jacket and hat. While he didn't actually serve in the military, the "Chairman of the Board" is depicted here in his role as an American prisoner of war attempting to escape from the Germans in World War II. The portrait measures 27x32" including matte and frame. It is signed by Simon along with the year of its creation, 2006.
Other past auction items that may be of interest to you.
Spring 2012 Catalog Auction