#3 Bobby gets fired
One of the defining aspects of Bobby's wonderful career was the chemistry he shared with Gorilla Monsoon. The two were a staple on WWF commentary from 1990 until December 1993, when Heenan planned to cut down his schedule and an offer from WCW would allow him to do so.
Rather than go with a simple "leaving" story, Heenan and Gorilla came up with one of the best segments in RAW history, where newly appointed commissioner, Monsoon, fired Heenan on camera and ejected him from the building along with his "belongings".
Both guys played this to the hilt and Heenan genuinely seemed distraught at the turn of events, however in real life, they were the best of friends and it is said they both cried for an hour after the show was over, knowing they wouldn't work together again.
When Gorilla Monsoon passed a few short years later, Bobby insisted on the unusual step of breaking kayfabe on Nitro to acknowledge the death of a "rival talent" during The Monday Night Wars.
Bobby Heenan and Gorilla Monsoon together were simply the greatest pair of commentators the business has ever seen, likened to great comedy acts like Abbot & Costello.