4: Audi TT
The original Audi TT needs no introduction as a car released in the latter part of 1998. But the TT offered a design that was ahead of its time in every sense of the word. There were no other cars that looked like the TT at the time it was released. Under the sheet metal was Porsche engineering, and this continued to its road manners (via Road & Track).
The TT has always been an understated and fun-to-drive sports car. The styling is iconic and still looks beautiful today. The great thing about the TT is that it has stayed in production for two decades, and even an early model still looks very modern. There are few cars that deliver the type of smiles the Audi TT does.