#5. Michael V.K. Wallstreet (aka I.R.S.)
Mike Rotunda has a deep connection with WWE. Not only did he hold the then-WWF tag team titles with Barry Windham as the team The 'U.S. Express" in the 80s, he portrayed the evil tax collector Irwin R. Shyster (aka I.R.S.) in the early to mid 90s, He's also the father of current WWE Universal Champion Bray Wyatt - oh, and Bo Dallas, too.
In between his first and second WWF runs, however, he ran with the gimmick of Michael Wallstreet - which was basically a rip-off of Ted Dibiase's "Million Dollar Man" persona (ironic, considering the two would team up in Vince McMahon's company eventually).
Rotunda, as the kayfabe story went, inherited a lot of money and invested it into the stock market. As he didn't want to give up being a pro wrestler, he used his newfound wealth to hire Alexandria York - the future Terri Runnells - to use her computer expertise to help him analyze his opponents (with computers) and come up with the proper strategy to defeat them.
Well... that didn't really work out.
After finishing his run as IRS in the WWF, he rejoined WCW as his old persona (with the added "V.K." to his name, as a hilarious reference to Vincent Kennedy McMahon), and eventually joined the nWo. The story eventually forced his character to leave the faction, and he continued on as an anti-WCW wrestler, but nobody really cared.
Rotunda has a Hall of Fame worthy career in the wrestling industry. His nWo run is not a factor in that.