2. The Outsiders (1996) Vs. D-Generation X (1997)
This doesn't quite fit into the criteria of the other entries for the simple fact that all of these men have wrestled each other multiple times while being in the same company together for a significant period. But a feud between the 4 Kliq members as their on-screen factions of the Outsiders and DX would have been big money. Even during this time period it was no secret to fans that these guys were best friends. The MSG curtain call that broke kayfabe (which had been dead for years anyway) was an influential moment with implications that affected the business in a major way. When DX attempted to "invade" WCW by showing up at their arenas during Nitro (and yes I realize this was after Shawn's departure but bear with me here), what if they had actually been met by Hall and Nash? Regardless which company the feud took place in (hopefully WWE due to their willingness to push the envelope) it would have been incredibly entertaining. The two groups would be constantly trying to one up each other on the mic and in the ring, and it would have been a treat to behold.