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For personal preference, my main criteria would be whoever entertained me the most during their career and was at least at a high level as a star. Being able to reinvent yourself to keep your lengthy career fresh is very helpful and not make it feel more like an old guy who is well past his expiration date in the ring and/or as a character.
Like Undertaker's lengthy career would be looked upon more fondly had he retired after his Mania streak was over since that was the last meaningful thing about his career.
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