Frank Sinatra in a Chrysler Imperial, 1980






Yes, that’s Ol’ Blue Eyes behind the wheel of a brand-new 1981 Chrysler Imperial. It was presented to Frank Sinatra in Detroit by his pal, Chrysler Chairman Lee Iacocca, in gratitude for Sinatra’s agreeing to promote the car without charge while the automaker was struggling to avoid bankruptcy. Sinatra appeared in print ads and television commercials in which he sang a specially penned song about the luxurious car called “It’s Time” … for Imperial. There was even a Frank Sinatra Edition of the auto, available only in Glacier Blue Crystal — supposedly to match the color of the singer’s celebrated peepers. That special edition included badging and a Mark Cross leather case with 16 cassette tapes of Sinatra songs. The Imperial had been made since 1926, but it didn’t have its own marque until 1955, so it could compete more directly with its luxury rivals — Cadillac and Lincoln. The Imperial was manufactured until 1975, then returned from 1981 to 1983.

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