25. 1969 Pontiac Trans Am – $250,000+
The Trans Am model became pretty popular and mass-produced in later generations. In 1969, it was a rare and unique limited edition car. But, at the time, the company was under a racing ban from GM. Pontiac introduced the Firebird Trans Am as a loaded version featuring big-block power because of its 400 V8 engine equipped with the Ram Air III or IV intake system to mask its intentions (via Supercars).
The difference between those engines was significant since Ram Air IV featured a lot of improved engine components. Moreover, it was rated at 366 HP but that wasn’t true. However, this particular version had signature white paint, blue stripes, and Rally II wheels. It proved to be a tough seller. Only 634 Firebird Trans Ams were sold. Among those, only eight of them were convertibles, making them extremely rare and sought after as a result.