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Why stupid people shouldn't have nice cars! #10. Bugatti EB110 - $500,000 You know these are expensive crashes when a $500,000 super-exotic barely makes it to #10 on the list. This 1992 Bugatti EB110 was being driven by a mechanic as part of its annual checkup. He claims there was an oil slick on the road which caused him to lose control and crash into a pole. The owner of the Bugatti is a famous "feel good" guru named Emile Ratelband. Not sure how good he was feeling after this wreck. #9. Pagani Zonda C12 S - $650,000 Only 15 Zonda C12 S were ever built but that didn't stop this owner from driving it like a bat out of hell. He crashed this beauty in the wee morning hours while driving in Hong Kong .  #8. Mercedes Benz SL 300 - $750,000 The SL 300 "Gullwing" represents the very finest of Mercedes. It is THE classic car. Unfortunately, there's been more than one crash involving this masterpiece. You're looking at a car that was once worth nearly a million dollars. The owner thought it would be a good idea to race it on the streets of Mexico . No, not a street race, but the annual "La Carrera Panamericana" race which is limited to classic cars produced before 1965.  #7. Jaguar XJ220 - $1 Million Here we have our first million dollar crash (and we're only #7 on the list). The XJ220 once held the record for highest top speed for a production car (217 mph).  #6. McLaren F1 - $1.25 Million The McLaren F1 took over the Jaguar XJ220 not only in price, but also highest top speed at 231 mph. (broken only in 2005). There were only 107 ever produced, and several destroyed. Including this one driven by Rowan Atkinson, the popular actor who plays "Mr. Bean". Atkinson has the unfortunate history of crashing multiple exotic cars, including an Aston Martin. #5. Ferrari Enzo - $1.3 Million The Ferrari Enzo sure seems to attract a lot of crashes. This is surprising considering the price tag. You would think the owners would be more careful, but we've documented at least 14 crashes involving the Enzo. That's nearly $20 million worth of crashes! The most famous was the Malibu crash of 2005, when the driver, "Fat Steven" Eriksson crashed the car at 196 mph. Below is the result. #4. Bugatti Veyron - $1.6 Million The Bugatti Veyron is the most expensive production car in history. And unbelievably, it didn't even make the top three on this list. Only 300 are expected to be produced and already two have crashed. Below is the first one. The driver thought it was okay to speed at 100 mph in the rain. He only had the car for one week. #3. 1959 Ferrari 250 GT TDF - $1.65 Million Now we start getting into the extremely rare classic cars. The owners who are willing to take these machines on the road are just plain crazy. The ones that take them on the track are even crazier. This 1959 Ferrari 250 GT "Tour de France" crashed into a wall at the Shell Ferrari-Maserati Historic Challenge back in 2003. #2. Ferrari 250 GT Spyder - $10 Million Just when you thought it couldn't get much more expensive, the damage has been multiplied. The record price for a 1961 250 GT California Spyder at auction was set on May 18, 2008 when a black one was sold for $10,894,900. So what is one doing buried in the sand? The unlucky owner had it stored near the beach when a Hurricane hit.  #1. Ferrari 250 GTO - $28.5 Million We now present you with the most expensive car crash ever. Touted as the Ferrari that most successfully embodies the traits of the marque, the 1962-64 Ferrari 250 GTO became the most valuable car in the world. In 2008 an anonymous English buyer bought a 250 GTO at auction for a record $28,500,000. The crash below represents a car worth more than the combined value of all 14 Enzos involved in accidents. It is simply unbelievable that an owner would even dare take this car on the road.  After a track event involving historic cars, the owner of this rare beast rammed into the back of another car after traffic slowed down.