4) Doink The Clown: If the entire Doink the Clown run was done by Matt Osbourne, he'd certainly rank higher. During his run in 1993, Osbourne absolutely nailed the Doink character. He not only delivered when in the ring, but he just got the character and made it work. His run as a heel was some of the finest stuff going in 1993 and he even did well when turning face. He was so enthralling in the role that it was hard to not list him. Unfortunately, he wasn't able to play Doink for the entire run and the multiple people who followed him just couldn't quite capture the magic. Their performances, along with the addition of Dink, made Doink into a joke and he became pretty unwatchable.
3) The Mountie: Maybe there were better options to list here to some, but dammit, I always enjoyed the Mountie. He was such a ridiculously goofy heel, but he threw himself into the role so well that he parlayed it into success. In 1992, he actually won the Intercontinental, and though it was only for a few days, it is still an accomplishment that a lot of guys with occupational gimmicks never got. Not only that, but a little over a year later, they added Pierre and made a tag team called the Quebecers. I've been watching Raws from 1993 and 1994 recently and have found that they were usually a highlight of the show. They even held the Tag Team Titles a few times. Not bad for an occupational gimmick.
2) Val Venis: The only occupational gimmick from the Attitude Era that fit in as well as Val's was the Godfather. I picked Val over him though for a few reasons. Val fucking nailed the porn star role. Seriously, remember his vignettes? They were unbelievably cheesy and had no right to work. But, Val threw himself into the role and I couldn't help but enjoy it. He had the voice and the mannerisms down and took something that shouldn't have worked and found success. He won multiple midcard titles, and did different things with the character to change things up, but always found a way to be relevant and over in an era crowded with top stars.
1) Big Bossman: When I read the theme for this top five, Big Bossman was the first guy to come to mind. He was one of the few guys that was able to make the gimmick work very well as both a face and a heel. He got very over in both situations and was always one of the better big men in the ring in history. When he left to WCW, things didn't work out so well but he always found a way to be rather relevant in the WWE. Even after returning in the Attitude Era, he changed things up donning the black Shield like attire and was a major part of the Corporation, even holding both the Hardcore and Tag Team Titles at the same time.