23. Pontiac GTO Judge Convertible – $440,000

By 1971, the end of the crazy muscle car segment was in sight. The government started tightening its grip on the segment, and cars began losing power and curb appeal as a result (via Mecum).

One of the last true muscle car convertibles was the 1971 Pontiac GTO Judge with a powerful 455 V8 engine and ragtop. The Pontiac made only 17 of them, and this is why it is worth so much to today’s collectors.