Built from 1991 to 1995, this Italian-made V16 supercar was originally designed as the Lamborghini Diablo. But when Chrysler purchased a stake in Lamborghini and the Diablo’s designers modified the plan, mastermind Marcelo Gandini took his original blueprints to automotive engineer Claudio Zampolli, who built it as a Cizeta. Cizeta built only a handful during the car’s initial production run, but they occasionally resurface on the market.

Porsche’s first production car, the rear-engine, rear-wheel drive Porsche 356, survived four high-flying generations before it was laid to rest in the mid-1960s. Considered the most highly developed of the four-cylinder Porsches, the 356 is also regarded by vintage car experts as the most fun to drive. Procuring one isn’t difficult: about half of the 76,000 cars originally produced survive.