1966 Pontiac GTO Convertible – $300,000
The Pontiac GTO changed the muscle car segment forever. There has never been another car that captivated the auto world as this GTO did. The performance of the car was the most impressive aspect, but the styling also became iconic. The GTO Convertible took everything the two-door did right and added an open-air feeling. There is no way to downplay just how important the GTO Convertible was to the automotive industry during this era (via Motor Trend).

The convertible has been fetching higher numbers on the auction block lately. There are very few muscle cars that people want as much as they want the GTO convertible. The fact that the car is so highly sought after is part of the reason that the value continues to rise. You’ll seldom find a car from this era that’s as notable as the GTO convertible.