The classic Chevelle model year that remains the most popular is the Chevelle SS or "Super Sport," which was introduced in 1966. The original model was brought out in 1961, but the Super Sport package was added in 1966, when it truly rose in popularity, according to HowStuffWorks.
The SS package included red-line tires, a black-out grill and stylized front fenders. Only approximately 100 models of the 1966 Chevelle SS 396 were made, making it one of the most sought-after vehicles in Chevrolet's history. It is also one of the most expensive resale cars, selling for hundreds of thousands of dollars in some cases.