Chevrolet Impala SS
The Impala SS was simply a Caprice with a paint job, but it ended up being a whole lot more. The car started a trend and a resurgence of American muscle cars. The Impala also became an iconic part of hip-hop culture, with the car being a cornerstone for the rap community after appearing in thousands of music videos (via Car Gurus).
A lot of famous people own an Impala SS as well, with Tim Allen being one of the most well-known. He has owned his Impala SS for decades now and it goes to show how great the car was. The simple design resonates with people who were kids in the 1990s and dreamed about owning one of these, so the price will keep climbing.