#1. Worst - Rocky Maivia
Here's the truth of the matter - Dwayne Johnson was always going to receive a top push. However, Vince McMahon decided at the time to take a more organic approach and that worked wonders, making Johnson one of the biggest stars in the industry's history.
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However, before that, Vince McMahon decided to give Johnson the gimmick of Rocky Maivia, in tribute to his grandfather the late, great High Chief Peter Maivia. The only problem was this - the gimmick was terrible.
Rocky came across as the most generic babyface in the world and had absolutely zero depth to him, with the WWE Universe quickly turning on him with chants like "Die Rocky Die". McMahon decided to go the organic route and when he returned from injury, told Johnson that he would turn heel so that he could get over organically.
And thus, 'The most electrifying man in sports entertainment', 'The Rock' was born. The rest, as they say, is history.
It would certainly be interesting to imagine the outcome of the Rocky Maivia gimmick if the fans had taken a liking to it.