Chevrolet Corvette C1
When you buy a Corvette, you're buying into something called, without irony, "the lifestyle." It's not as cultlike as it sounds and mostly involves sitting in lawn chairs with other elastic-waist bandoleros discussing the merits of fiberglass bodies and composite leaf springs. But if you care about the cars and don't mind the culture, we direct you to this 1958 example.
Some Vetteheads claim the only Corvette to get is a second-generation Sting Ray. These '63–'67 models established the Corvette as America's world-beating sports car – but only briefly, as subsequent generations quickly achieved official-car status in the demimonde of cokeheads and Dirk Diggler types. We argue, however, that the Corvette party got started earlier, with this 1958 model. For 1958, the 'Vette was mean, with a leaner grille, quad headlights, a body 10 inches longer than its 1957 predecessor, and a gross output as high as 290 hp. This was also the first Corvette to turn a profit, which validated the whole "America's sports car" enterprise and made possible the Sting Ray everyone's always yammering about.
Unlike with most collector cars, the biggest price-determining factor here is not condition or mileage, but equipment. A base, 283-cubic-inch-engined car can be had for $40,000, but a first-gen convertible with fuel injection will demand serious money. Hey, with a fiberglass body, at least you won't have to worry about rusty doors.
What to watch out for: If you buy a fuel-injected car, spend the money to keep the mechanical system in tune. Otherwise, these cars are pretty bulletproof.