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Since I grew up watching James Bond movies, I have to go with a modern(ish) Aston Martin. They all look the same after the DB7, so take your pick. I can almost imagine a world where I can afford a used 2008 Vantage V8. For me, a cool sports car can't look out of place parked on the side of a road in a decent part of town. I saw an Audi R8 parked on a road in Lower Queen Anne in Seattle, and it looked fantastic. Maybe not the coolest, but it's up there on my list. I'm personally not a fan of the Corvette. Along with Lamborghinis, they're too ostentatious to be cool.