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I agree with Jeff Jarrett being on the Lucky list, but I would also add Jerry Lawler to that argument:
Kid who just wanted to be an artist randomly gets to "give it one try" and goes on to have a career many would give their souls for. Never really gets a full shot in WWE but is so well-established from his territory days that any time he wanted to have a match, he gets instant credibility. Then suffers a heart attack on air while world-class medical personnel are in the same building and save his life.
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