The 5 Worst Deals In the History of Handshakes

#2. A Little Old Lady Cheats Death (and a Lawyer)

One day back in 1975, a dapper middle-aged French lawyer by the name of Andre-Francois Raffray had a devil of an idea: He sought out a 90-year-old woman named Jeanne Calment, who was currently living in a very nice apartment indeed, and offered a deal: He would pay her 2,500 francs ($500) a month for the rest of her life if, when she died, he could take over the apartment regardless of how much money had been paid in total. The benefits were obvious: Once the old lady kicked the bucket a few months later, the Frenchman would move in after paying only a fraction of the actual cost of the apartment, presumably while twirling his mustache and cackling diabolically at the foolishness of the sweet old crone.

Fortunately for Raffray, she agreed. Unfortunately for Raffray, things most decidedly did not go according to plan. There were a few warning signs of what went wrong: Jeanne's mother had lived to 86, her father to 93 and her brother to 96, while Jeanne herself was unusually active, taking up goddamn fencing lessons at the age of 85. When most people stop controlling their bowels, she was just starting to learn swordplay. Even so, nobody was prepared for what happened next: Namely, that Mrs. Calment would live to be the oldest person in the history of the world.

The months turned into years into decades, with no sign of the old biddy dropping dead anytime soon. All this would only have made the moment Raffray finally moved into the apartment all the sweeter... if the old biddy in question hadn't outlived him. Yes, that's right: After 30 years of waiting impatiently, Raffray died before he could collect. What's worse is that his wife was forced to continue the payments, as the contract was over only when Jeanne kicked the bucket. She eventually shuffled off the mortal coil at the age of 122, and had been paid a total of over $180,000--twice what the apartment was worth.

#1. John Fogerty Rips Himself Off (Twice)

John Fogerty was the singer, songwriter, guitarist and general creative force behind classic rock band and mom aphrodisiac, Creedence Clearwater Revival. Due to a falling out between its members (either Fogerty being a dick or an overworked genius, depending on who you ask), CCR disbanded in 1972. Which was a problem since Fogerty had been representing the band himself, and had signed them all to an insane 14-album deal. To give some context, the Beatles, in their long and prolific history, only produced 13 records. CCR had made six. Eventually the problem was resolved when Fogerty gave the rights to every CCR song to Fantasy in exchange for letting him leave the band, which is like resolving a roach infestation by giving the bugs your keys and moving to North Dakota.

That'll show 'em.

This meant that for the rest of Fogerty's life, he could never make money from, nor even play, the songs that he made famous; songs that still get airplay today. His ensuing solo career was pretty much what you've come to expect from "solo careers": A dismal downward spiral that ends in a Sambuca-flavored vomit puddle outside the wedding gig you're doing for "dibs on the buffet leftovers." Fogerty was understandably a little miffed at this whole thing, and recorded a scathing song called "Zanz Kant Danz" about the CEO who helped him screw himself over. In retaliation, Zaentz and Fantasy Records brought a plagiarism suit against Fogerty for infringing on one of the other songs they owned, called "The Old Man Down the Road." So who did John Fogerty allegedly steal this song from?

One Mr. John Fogerty.

Fantasy claimed that he ripped off one of his old Creedence tunes to use in his solo career, and since they owned the entire catalogue, they decided to bring him to court. And while the justice system, proving it wasn't completely insane, eventually upheld Fogerty's right to take inspiration from himself, he did have to change the title of his other song to "Vanz Kant Danz," doubtlessly confusing many fans as he apparently penned a scathing rock retort to a shoe company.

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For more people who would be envious of these deals, check out The 5 Ballsiest Con Artists of All Time. And find out what their apologies would be on par with, in The 6 Most Insincere Apologies of All-Time.

And stop by our Top Picks (Updated 06.09.10) to see the deal Popsicle Pete made with satan.

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