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It's cartoonish to me. A cartoon Englishman with his monocle and his brandy glass, all wrapped up in tweed and smoking a pipe.

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I have never met a Rupert, not even a dog. The only Rupert I know about besides Rupert Murdoch is, years ago the local radio station ran commercials for a used-car parts yard and later a beachfront restaurant, and the pitchman was this guy doing a goofy redneck impersonation and calling himself Rupert. So I also think of it as a hillbilly cartoonish name.