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My in laws flew out to visit us once, in about 1982, and rented a Lincoln. which I drove to work one morning because it had my car blocked in the driveway. In terms of the actual blue-book value of the car as is, expressed in today's dollars, that would probably be it. But I have owned a few cars that had originally had high value (but not by the time I got them), Jaguar and Volvo and Rover. Actually, I bought a new Volvo in 1964, for $2300. Would that count? The last new car I bought was a '78 Dodge Colt, for just over $4,000. I don't really know how to define "expensive" in this context.
The most expensive car that I have ever driven was my uncle's incredible 1964 Imperial LeBaron.
To this day, I am amazed that he allowed me, at the age of only 17, to drive this behemoth.
About a month ago I was in Germany and rented a nearly new BMW 650i coupe primarily for autobahn driving. I think it was about a $100k car. I had a grin on my face pretty much the whole time!
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