A few discussions to get things started:
Lotus Elise. The first time I saw one of these on the highway, I trailed it for three exits trying to figure out what in the world it was. I was in love. When I got to work, I googled "Lotus," the only badge I could see, and was in love with the idea of a four cylinder that could compete with a Corvette. Maybe it's a little more pedestrian in Britain, where I'd imagine it's more common, but I've only seen a few here. Someone who drives a Lotus has a very particular taste, and knows what he/she wants. What's not to love?
Porsche 911. This has been the sportscar for longer than I've been alive. At this rate, I suspect it will be adorning bedroom walls long after I'm gone.
Mazda MX-5. This is a personal favorite, so there's no shock that I think it's cool. It's the best of both worlds, Japanese reliability and the fun of a British sportscar. It's got a strong aftermarket (Flyin Miata, anyone?), but has avoided the ridiculous ricer culture that seems to ruin any halfway decent sportscar that comes out of Japan.
Corvette (Current Gen). This has always been the best bang for the buck in the sportscar world, and it's a nice car to boot. Still, it's a bit of a standard choice. I can't see calling it sub-zero, but it's definitely cool.
Nissan GT-R. I almost wanted to call this one uncool. I don't like it. The design does nothing for me. Then again, the car has a following, and there's no doubt that it's a performer. I don't think it's a rival to the Corvette (AWD and a rear seat will target a different demographic, I think), but it's definitely got a following.
BMW M3. BMW's are cool, but just barely. They're quite possibly the perfect compromise between livability and performance, arguably the ideal entertaining but practical daily driver. The look, however, is at best a bit boring, even on the M's. Sorry, Bimmer. The chassis is sub zero, and the body on top of it is uncool. Sorry, Bimmer, but I'll split the difference and admit that it's cool.
Porsche Boxster. A Porsche Boxster says one thing: "I wish I'd gotten the 911."
Honda Civic. This car says one thing: I think my FF economy car is a 911. It's not the people who want a reliable form of transportation that ruin this car. It's the aftermarket folks who do it. I despise the ridiculous body kits, the rear spoilers for massive downforce on a FWD car (WTF???), the careful weight reduction in the body panels just to add 500 lbs of speakers and amps for a sound system....I could go on, but I think I'll stop here.
Hummer H3. This is an attempt to be manly while buying a soccer mom SUV. If you're going to drive a soccer mom SUV, that's fine, but don't try to hide it behind a badge.
VW New Beetle. I liked the old beetle. The rear engine small car with lots of customization options in the aftermarket was everything the Civic should be. The new one, though, is truly sad. A front-engine, FWD layout is a disappointment, and they've turned it into a girl car. What's worse, the really hot girls don't drive them; the annoying chubby girls with who think they're far hotter than they are do.
Well, those are the choices for now. Feel free to agree, disagree, or even flame a bit (that's the point, really). If you want to start your own, then please do. Actually, that would be particularly fun. Anyway....thoughts?