I won my first car in a drawing.
The year was 1989 and the car was a 1972 Chevy Impala.
The drawing was held at a used car lot. They were giving away three used cars - the other two were equally as old. There were no age restrictions or limitations on how many times you could enter so, being a normal 15-year old boy, I filled out maybe 200 entry forms. There were only a couple of hundred people there for the drawing, so my odds were pretty good. I won the second car they gave away. When they drew for the third, the guy took out a form, shook his head, then picked again, so it's possible that I may have been picked that time as well.
My mom was in disbelief - not because I won a fabulous prize, but because we now had to find a way to get it home - so my uncle had to pick up my dad to bring him up there to drive the other car home. This became my first car. It was actually the best of the three that they gave away - I believe it was the only one that was able to be driven away under its' own power.
It was perhaps the largest car ever built. I could lay down flat in the back seat, which proved helpful. It had a large 350 v8 motor, which was still pretty quick, despite the car weighing the same as a WWII battleship. And it ran on regular gas (at a time when regular gas was no longer sold), so I had to have bottles of lead additive on-hand for every time that I filled up the gas tank.
After graduating high school, I sold the car for $500 to a buddy's sister who immediately put oil where the transmission fluid went, or vice versa, and killed it.
Edited to add a couple of pictures of a 1972 Impala for reference.
The coolest feature was the back window, which was v-shaped: