Chevy SSR Pickup

The SSR pickup had the same identity crisis as the Chevy El Camino — car, truck or both? — along with the added complication of being a convertible. "Car companies are always trying to fit niches," Hagerty says. The SSR was certainly in its very own niche, but trying to be too many things at once didn't attract quite enough buyers. Chevy sold fewer than 10,000 SSR pickups in their first year of production, 2003. "When they sell single-digit thousands or less, it truly is a flop," Hagerty says.

Collector prognosis: The car-truck-convertible shtick has already secured a hearty following of enthusiasts.