Original Aston Martin DB5
Original Jaguar E-type
Original Shelby Cobra
Original Ferrari 250 GTO
and a newish Audi RS4 for daily driving.
I would add in a bunch more cool cars (such as some classic muscle, some awsome 4x4/truck, some modern exotic like the Porsche 911 Sports Classic...but if its only 5, then the above is it).
-a