Tesla - I got rich on tech and you didn’t. Oh, by the way, it’s green. I don’t really care about that but it certainly adds to the coolness factor that I am so desperate to rub in your face.
Could be.
But, in fact, Whiskey Dickens is right. many of these stereotypes are outdated. But then so are many of the cars out there right now. Some of the newer Caddies are really, really nice to drive and race, but they still have GM reliability issues.
Ford Escape/Chevrolet Equinox/Jeep Grand Cherokee - Yeah, I have kids but I’m still totally hip.
Yeah, okay. Cadillac screams Florida alterkaker, and you and everyone else knows it. Try as you might to convince others that Cadillac is a cool car, they will continue to laugh at the thought. The day of the Cadillac is over; the manufacturer is simply in denial.
I bet you’re fun at parties. :smack:
…and Hair Club for Men is costing me a fucking fortune!
I think you’re the one denying the complete revolution Caddy has made in the last ten years. You realize many of them share engines with the Corvette and Camaro - the really hot ones?
They tend to come up a little short against BMW and Mercedes - fit and finish and interior are not quite up to those standards - but they are hardly pretenders. And they haven’t had a quarter vinyl roof or opera windows for quite some time.
Want to bet? I know plenty of women driving giant Rams, usually because they work in jobs where that level of hauling capacity is necessary, but some just like giant trucks.
Or just gay.
Corvette - an asshole slowly losing his hair
Subaru Forester with 2 or more ladies in it – lesbians
(Slightly-built, twenty-something guy across the street from us)
Fall/Winter: Dodge Ram pickup, jacked up way high, various yeehaw accessories & stickers, big Diesel with (apparently) no muffler;
Spring/Summer: Harley Hawg, window-rattling loud; outlaw-wannabe hanky-headband;
Our affectionate name for him: “Dickless”
1994 Honda Civic SI hatchback: I am coolness incarnate.
Does it have bumper nuts? Tell me it has bumper nuts.
The Subaru WRX STI: a car for sensible, mundane folks.
Quite.
“…with brain damage.” 
(Most of the makes above have at least one insanity-mobile in their current or past lines…)
No, bumper nuts are a sure sign the truck is owned by a woman. A redneck woman.
PT Cruiser: elderly person, or young person who was given (saddled with) an elderly relative’s PT Cruiser
Any crossover SUV: I think I am fooling everybody (and myself) that its cooler than driving a mini-van
Don’t care. I wouldn’t be caught dead in a Cadillac…well, maybe if I’m dead because I wouldn’t know any better. There is nothing Cadillac could do, including reducing the price of a car to a dime, that would earn my business. As far as I am concerned, the brand is poison.
Revolution, schmevolution. It’s a Cadillac. Clunk! Clunk I tell you. How’s that for a 21st century perception of an automotive anachronism? 
Cadillac’s commercial that they played during the Olympics turned me off to the brand. “Do you know what’s more important in life than spending time with your family? Working hard so that you can have stuff. Stuff including a Cadillac”.
So if Cadillac wants you to think that people who drive them are materialistic workaholics, if that’s the image that the brand is encouraging, I wonder what sort of connotations they’re trying to fight.
I like to think that my Mazdas (2012 CX-9 GT SUV and 2014 Mazda6 GT Sedan) say that I enjoy driving and I buy cars that are fun to drive! =) I looked at the Acura MDX and a few other ‘premium’ brand SUVs before buying the CX-9, but I liked the Mazda better.
A lot of the ‘upscale’ brands just scream “douche-bag”…