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If skiing downhill at unimaginable speeds is extreme, than skiing downhill and jumping over cliffs is just about as batty as it gets. Sure, ski jumping is an official winter sport, but ski cliff jumpers take this sport off the straight track and into the unknown. The world record for the highest cliff jump on skis is 255 feet, set at Grand Targhee, Wyoming, and is held by Jamie Pierre, who survived the perilous jump but died tragically in an avalanche in 2011.