I'm of two minds on this "greatest cars" thing. Obviously, cars like the Aston Martin and the Maserati qualify as some of the greatest cars ever, and I love them both (as well as the E-type, and assorted Ferraris and other super cars).
On the other hand, I think there's a case to be made that greatest can mean a lot of things- not just the fastest or most sumptious or most expensive. Great can also mean affordable, for example. Sure, an Aston Martin is a beautiful piece of machinery to lust after, but realistically, it has many more admirers than people actually capable of purchasing one. But a classic MG or Triumph- those are also beautiful cars, and are a realistic dream for the average car enthusiast. Same for the new Coopers.
My last car was a 1990 Alfa Romeo Quadrifoglio Spider. A beautiful red piece of Pininfarina art on wheels. Affordable both at purchase ($10,500), and to operate (30 miles per gallon), and to service (same labor rate as my mom's Subaru). And because it wa relatively rare, almost nobody knew what it was, and was often mistaken for a Ferrari (well, by your average uninformed motorist). It got tons of admiring looks for a car that cost me less- way less- than the cars its admirers were driving. To me, that made it a great car. Sure, the Maserati is faster, but the Alfa Romeo was a dream that was realistic to achieve.
Sadly, my beautiful piece of automotive art was destroyed by a 17 year old girl in a sport ute. I was stopped at a red light, waiting for the light to change, when this teenager driving way too much car drove right into the back of my car, without ever bothering to apply her brakes. She told me it was the second time she had done that in a year and a half of driving. The State of Oregon, in its wisdom, suspended my license because I was uninsured; the other driver is still out there, prowling Oregon with her lethal weapon.
Below is a 1987 Spider Quadrifoglio, almost as beautiful as my 1990.
This is the car I am going to drive in 10 years, hopefully
