The criteria I'd make for cool would be, a car someone would really want, like they'd see it drive by and think "I am going to buy that one day", or a car someone would have a poster of in their cubicle/bedroom. Like an American Muscle Car such as a Mustang, or a Luxury car, such as a Rolls-Royce or an exotic sports car like a Ferrari, Lamborghini or Porsche
So what 'cool' cars would you say your family owns or has owned? I thought of this when I realised nobody in my family actually has owned anything worth noting.
My Grandfather owned a 1987 Pontiac Trans Am GTA after seeing K.I.T.T. on Knight Rider and kept it for about 2 years. My mother and uncle could barely fit in the car, but my Grandpa loved it. It wasn't until 1989 when he went to visit family that some drunk teenagers in a Oldsmobile Cutlass Supreme smashed into the door and front wheel arch making the car permanently immobile. After that my Grandpa moved on to less interesting cars such as a Pontiac Bonneville ('89), Pontiac Grand Prix ('95), Mercedes ML350 ('99) and '09 Mazda CX9. He ironically bought his wife a '96 Cutlass Supreme.
My Father currently owns a 2004 Z4 2.5i, but I don't find it cool enough, I feel like the Z4 M would be 'cool enough'.
Edit: Also for a funny image, my Grandpa looked like a young Ghandi with wavy hair in the late 80s.