In 1999, David Phillips spotted a Healthy Choice promotion: 1,000 airline miles for every 10 barcodes. During the bonus window, that doubled.
He found pudding cups at 25 cents each, bought 12,150 of them for $3,140, and donated them all to the Salvation Army — earning an $815 tax deduction.
Total haul: 1,253,000 frequent flyer miles and lifetime Gold status. His story inspired the Adam Sandler film Punch-Drunk Love.