5. Alfa Romeo 33 Stradale
As with the Lancia Stratos, the 33 Stradale was the road-going version of a much faster pure-bred race car, but unlike the Lancia, they only made 18 examples of the Alfa. It's entirely possible that you will never come closer to owning a street-legal classic Italian racer, and one could certainly make an argument for placing this higher up on the list, but it's so rare that you're unlikely to ever see one in person, let alone driving on the roads. It loses points for being the prettiest girl without a prom date.