42. Dean Martin

When we think of Dean Martin, we think of the smooth and sophisticated crooner of the 1950s and 1960s; a member of the 'Rat Pack' who was good friends with Frank Sinatra and the rest of the gang. It's harder to imagine him as a frail and less stylish old man, but that's how he ended up. Martin kept a lower profile in the later years of his life, but he was still occasionally caught by the lens of the paparazzi, which is precisely what's happened here.

The photo was taken in early December of 1995 as Martin and friends left a restaurant. By this time, the 78-year-old-Martin was already suffering from terminal lung cancer, and would have been aware that his time on Earth was drawing to a close. He succumbed to respiratory failure on Christmas Day that year.

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