My first car is my 1989 Chevy Caprice. I was all excited about getting my license, and a month before my 16th birthday, I still hadn't found a car to drive yet. I really wanted a pickup, but they were proving to be either complete piles of junk, or they were more than I could afford.
One day w/the family at the beach for a little summer sun-n-fun, my dad said that one of my uncles knew someone who had a nice Chevy Caprice with really low miles. At first, I couldn't stand the thought of driving "Grandma's" car, and said there wasn't any way in hell I was going to drive that thing... but the more I thought about it, and the more of them I saw, the more I liked them, until one weekend, we found ourselves in Detroit looking at it when we visited my Grandma.
A week later, I was back, getting the keys to my like-new, 33400 mile Chevy Caprice, for $1800. Now, 6 years and probably close to $8000 later, the wheezing 305 is gone, replaced by a healther 355, a TH350 in place of the 200-4r, and a nice 8.5" 10 bolt out back w/some good 3.73 gears. Grandma's grocery getter looks like some sort of cop car on steroids from the distance. Surprises many a Camaro, Mustang, and wanna-be ricers.