18: 1966 Porsche 911 – $275,000
Again building on that original and beautiful shape, the 1966 Porsche 911 doesn’t look like anything else on the market. The interesting thing about the 1966 Porsche 911 is that it isn’t particularly amazing on paper. But the purest design and the performance more than make up for it in the long run. You take the drawbacks of any classic sports car with a grain of salt, so naturally, the 911 falls into this category.

As Seinfeld has pointed out in previous episodes of his TV show, the 911 is a sheer joy to drive. This is what makes it such a standout car from several perspectives, and the auction price of the car points that out.