My first car period was the 68 Cougar that I have now. I can't say that I bought it because it was free. My Grandfather was the original owner and passed it down to me when it was 10 years old. I was 12. That was in 1978. My Dad passed down a couple of beaters that I used through high school and college in the 80s.
The first car that I actually paid money for was, coincidentally, a G-Body 86 Grand Prix that I bought in 1989. Parents co-signed a loan for me and everything. It appeared beautiful when I first looked at it and purchased it. Unfortunately, I was pretty naïve at the time of the purchase and let first impressions cloud my judgement. Several months after getting it home I started noticing things that weren't quite right.
Upon closer inspection, I figured out that the car was wrecked previously, but I continued to work towards making it better and fixing the stuff that wasn't right. When I finally got everything sorted, I put it back up for sale with the hope of just getting my purchase price back. Nobody would give me my asking price. So I decided to keep it.
About 6 months later I got T-Boned in the driver's door by a carload of drunk teens in a terrible snowstorm. The wreck, blew all the window glass out, moved the steering column to the middle of the dash, buckled the roof, folded the backseat in half, ripped the rear axle out of the frame, and put me in the hospital overnight.
I was fine afterwards but obviously the car was totaled. Their insurance company was nervous that I was going to sue due to their underage drinking, that they settled REALLY fast and paid me over a $1,000 above what I couldn't sell the car for earlier that year. With the insurance money, I went and bought my 88 Thunderbird, which is really the car I wanted to begin with and couldn't afford when I bought the GP. And..... I still have the T-Bird almost 30 years later.