1965 Pontiac Catalina (Worst)
The Pontiac Catalina had what it took to be a real contender in the automotive world. The styling of the car looked excellent, the standard features were on point, and the price offered affordability. But the Catalina did not provide a reliable ride when it first hit the market. Pontiac rectified many issues with the Catalina, but the sales numbers never recovered (via Fifties Web).
With the current classic car bubble, the Catalina has become sought after. The car does bear a resemblance to the GTO, which is great if you just want an affordable classic car. The Catalina has a large aftermarket community and there are plenty of enthusiasts who can help you with parts and customization.