My first car was a 1989 Cadillac Elderado, when I was 15. It had been keyed, but being my first car, didn't really bother me. After I bought it, the car had problems from the get go, and I let it sit for a while. Water happen to get inside through the sunroof, and it started to mold on the interior. Bought it for 1 grand, and sold it for 100 bucks. Got screwed on that deal. Yet, I still miss that car at times.
My second car was a 1989 Dodge Shadow, paid 300 for it with only 94k miles at the time, and I was 16 when I bought that. It didn't have much rust on it, and the only problem was the flywheel was missing some teeth. So when you go to start it, it would make noises, when ever it went over that spot. I don't have a good picture of it, but here's one of me, working on getting some things done, before I pull the engine and tranny out.
I still have the Shadow, but the fuel pump is shot, so it doesn't run for more than 2 seconds. I believe it's in the gas tank, but I don't want to risk the floor coming with it, when I pull the gas tank. I've had the car for four years. 300 dollars well spent. One time the heater core valve went out, so I had no heat. I had about a 35-40 minute drive back home, and I realized I had no heat, while it was -14 degrees outside. I was cold on my way home.
So now, I have a Grand Prix, and I plan on keeping this car for a while.
One good thing about all the cars that I had, I was able to pay for them with my own money, except for the Grand Prix, had to borrow $500 from my parents, which isn't to bad considering the car after taxes, and licenses came out to $6300.