#1. Brian Pillman tricks Eric Bischoff into letting him leave WCW for WWE
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Let's talk about how Brian Pillman got to WWE. It's one of the most fascinating stories in all of pro wrestling.
There's no way a list like this doesn't include the "Loose Cannon" Brian Pillman, much less in the #1 spot. But, here he is. And, it's a #1 spot (and appropriately for Pillman) with a bullet. From calling a particular wrestler (no relation) "booker man" to pulling a gun on Stone Cold Steve Austin in WWE, Brian Pillman kept you guessing and never let up.
Is this man the funniest man in wrestling?
In fact, that "booker man" incident - Pillman was scheduled to face then-WCW booker Kevin Sullivan (again, no relation) at the February 1996 SuperBrawl VI - is what started this entire entry. Before the match could even begin, Pillman grabbed a microphone and shouted the following:
According to his autobiography, then-WCW President Eric Bischoff had concocted a plan with Pillman that would see Pillman get his release from WCW and move on to ECW, where he would build the "Loose Cannon" gimmick even more.
The intention was that after working in ECW for a certain amount of time, Pillman would re-sign with WCW an even bigger star.
Pillman did, indeed, work with ECW following this, and even cut one of his all-time greatest promos:
The joke was on WCW, however, as Pillman would take this opportunity not to return to Atlanta. He instead chose to sign what was only the second guaranteed contract ever for a wrestler in WWE history (fun fact: the first was signed by Marc Mero).
Pillman would go on to have memorable feuds with both his former Hollywood Blondes tag partner Stone Cold Steve Austin and Goldust, before passing away in 1997. While his time in WWE was cut short, the way he got to the company was legendary.