#3 Val Venis
When Sean Morley joined the WWF in 1998, his character was a first for the company.
As the company and its fans embraced a new-found Attitude, Morley's character was the envelope-pushing Val Venis, a former adult film actor turned wrestler. Whilst a goofy character like this would presumably doom a young up-and-comer today, Venis definitely made it work, capturing the European and Intercontinental titles during his time.
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The problem with Venis though, is that he was a product of the times, as the company embraced edginess and controversial gimmicks, though this time could only last for so long. By his final years in the company, Venis' adult-past was completely dropped, as he became just another Superstar.
Now with a PG rating, don't expect anyone of Venis' profession to make the jump to WWE anytime soon.