My first car was a 1968 Pontiac Tempest. As a teenager I spent all of my money and time fixing it up and as soon as it was finished I totaled it out on my way to get flowers for my girlfriend.
Soon after that I purchased a 1961 mercury parklane in nearly perfect condition with less than 50,000 miles for only $250. The trunk alone was so huge that you had to climb in to get to the back. Sure wish I still had that car. Oh yes, in case your wondering, no, I didn't crash that one.