Owen Hart
In 1999, Owen Hart was about to challenge for the Intercontinental Championship. WWF decided on a character-appropriate entrance for Hart. The plan was for him to descend from the rafters into the ring. Before the event, the concerned personnel successfully tested the entrance.
Unfortunately, while making the actual entrance, Hart accidentally activated the early release mechanism. He was 78 feet above the ring at the time. As a result, he fell chest-first into the ring. After the on-site staff failed to revive Hart, he was taken to a hospital, where he died before midnight.