Admittedly I'm biased towards older cars due to the nostalgia of my age. When I was a little kid in the 70's I looked up to older kids who drove late 60's, early 70's muscle cars; Camaros, Mustangs, Chargers and of course European cars from the 60's were their own brand of cool. Alpha Romeo, Jags and Astons just reeked cool.
There were working class, cool cars that afforded style much before practicality and safety and even most of the time performance was less important than poise.
Looking at today's product line up from the American, Japanese and Euro market it's hard, for me at least, to get my salivation glands going. Sure, there's practical cars that have interesting body styles and technology packages that are nifty. But for me there are no cars that encapsulate 'cool', at least in a price range affordable to the average working person.
In 1970 the American Big Three put out probably 20 awesomely cool models. Hell, Mopar alone made up half of my list of cars that make me think "BAD ASS!" But the recent attempts to revive the Mustang or Camaro or Challenger looks like sad vestiges of what once was, not innovations or at least an introduction in to what could be considered tasty for a new century.
Toyota and Honda for instance don't even make pretense at selling an affordable sports car. The promise of a new NSX or Supra became stale ten years ago. We're no longer waiting.
The Corvette hasn't really been a cool car since the split window coupe. It's a disco chariot. I'm sorry. As is the Mustang from anything beyond the Mach I nor the Camaro once they started making it out of fibre glass with IROC emblazoned on it's side.
Modern European sports cars are neat. Again, keeping the price within affordability the Audi S5 is sweet looking as is the latest M3 but style is not their function, it's just tinsel on cars that are designed to perform foremost.
Just fucking bring back tail fins.