It is a tough question to answer these days. I've spent days pondering about it to myself.
I remember back in the early 2000s when the new MINI came out. That was an undoubtedly cool car that came around at the exact right time. Gas was getting more expensive, and people were getting sick of the SUV. Suddenly here comes this sleek hatchback smaller than most peoples' televisions, and cool was reborn. Driving a MINI was a way to send a message to the crew-cut egomaniac in the Hummer H2 next to you that said, "you've got it all wrong buddy."
But then, somewhere around 2007 everything went horribly wrong. Gas got even more expensive, and people decided that what was cool was fuel economy. And along the way someone thought that burning less fuel was "green."
That was when the Prius became the coolest car out there... sort of.
Everyone in Hollywood was parking a Prius next to their Suburban to show off their "love" for Mother Earth. Countless in-your-face vanity plates about being "green" were bolted on to hybrids. Hyper-milers started tailgating semi trucks and called it "drafting."
From my perspective it seemed that people's love for their Priuses (how do you pluralize Prius anyways?) was about as authentic as a trophy wife's love for her rich lawyer husband. It was more of a love for status and image instead of one based on true characteristics.
Since the green boom and the reign of the Prius many have tried to capture the cool status and failed. Smart is still one of the slowest selling brands in the country. The Honda Insight got some of the nastiest reviews I've ever read. The Nissan Cube might just be a little too funky for the 'States.The Fiesta has been a marketing frenzy, but just doesn't live up to the hype.
Could the Nissan Leaf really be the next cool car? It sure does one-up the Prius in the green category. It doesn't even burn gasoline. It's got that same sort of Japanese cuteness about it you would find in a Pokemon. Or, is it just going to introduce more people to the obvious shortcomings of the current generation of electric cars?
Does generation-Y even care?
Probably not. Most of us probably wont be able to afford the lease on a Leaf for a number of years. By the time we're signing loans, the hybrid will be a thing of the past.
The coolest car to us is really whatever we can afford. Some of us (or our parents) can afford Range Rovers or big Lexus sedans, while others can hardly even afford a beat up Festiva. There isn't anything truly universal with our generation, because the Internet has given us access to everything we could ever imagine.
If you asked me, I'd say it might be the upcoming Fiat 500. We will just have to wait and see.