The coolest people in this world are the underdogs that climb out of a hopeless pit and make something great of themselves. In high school, the rich/beautiful clic might be popular and thought of as cool at first, but when a select few kids start making their name in sports by doing the above mentioned, they will become so much cooler than the established clic could ever hope to be.
The Chrysler 300, for this very reasoning, is unwaveringly cool; from the pits of Detroit's underbelly came this testament to the working man's sophistication. The 300 is a status symbol to how far the owner has come.
These Opposite Locker posts are meant for car enthusiasts, however, the idea of what makes a car cool is not the inherit nature of asking if one would want to own, drive, or hoon such a particular vehicle (although, these may be contributing factors).
I would love to daily drive an original Lancia Stratos, but would that car help me entice a member of the opposite sex back to the nest? With the Lancia's overly-brutal suspension, engineering simplicity, and the 99.99% chance that it will most certainly break down on the way anywhere, you can bet your virginity it won't!
However, the opposite end of the locker bay, let's say an original Prius, won't help you reach any further ...unless of course, you've met an eco-mentalist. But we're still car enthusiasts, and life is too short.
So, what makes a car cool, anyways?
Another example. The Porsche Panamera is a business car for people who want to boast numbers but don't want any glorious sound track or good looks to go along with that; to anybody else, you're just like all of those 3 series drivers, but with a car that can offend mountains. The Maserati Quattroporte, on the other hand, is just a professional hitman's car, and we all love it for that.