My first car was an 85 Monte Carlo SS (still own it) that I bought from my Aunt. My uncle forced her to buy it in 1989 and sold it to me when I was 14. It was painful to look at it for a year and a half.
I am 30 now, so when I was 16 driving it around in 2001 I would get hassled nonstop from older guys trying to buy it. This was before a whole lot of ebay and craigslisting (at least for me) so I wasn't too keen on the value of it but I only payed $2,500 for it and knew I wouldn't be able to get it back for that.
Glad I didn't cave. I still get hounded now, though it's slightly louder with a 450hp 383 I built for it when I was 17.