I read DB Cooper: The Real McCoy about a year ago. It takes the evidence from the heist/disappearace and links it with a former military pilot named McCoy who was unable to fly professionally because he had a health problem and was in a financial jam. It all matches up so well that when one finishes the book, they are virtually certain that McCoy was DB Cooper (as the press dubbed him). He tried two "ransoms" like this. In the first one, the one that everyone remembers and that this movie is based on, he actually gets separated from the money as he was jumping and couldn't find it after he got on the ground. Who can blame him, it was Thanksgiving night in the pacific northwest and the weather was horrible when he jumped.
After the second one, which was much smaller in scale, the cops nabbed him right away, but he never confessed to being DB Cooper. He later escaped from jail and was killed in a shootout with police.
Interesting idea as far as movies go (other than the corny music), but if you want more info on the case, read the book.