Mine would be the previous owner driving off the side of the road doing about 25 and running into a rather large and immovable Caddy. Damages were the bumper, fender, hood and radiator support.
The poor little 65 had only 63,000 original miles on it. 230 inline 6, Powerglide, post model, poorly slopped on cover paint job, made in Massachusetts, and never driven out of the state. (Still hasn't)
But, with a few body repairs, needed changes to the drivetrain, interior, and many hours of work, it still only has 70,000 miles on it, but isnt so "poor" anymore. Rather healthy.
So whats the funny part? Him losing such a great little car!