5 Most Important Matches In WWE Monday Night Raw History

Looking back at some fonder milestones after the latest ratings decline...

Man, what happened to Monday Night Raw? I know the pandemic has put constraints on everybody, but even before then, what happened to the must-see nature of the program? Two of the three most-watched Raw episodes in 2019 were the post-WrestleMania show (typical) and the "Raw Reunion" show where the heroes of the 50+ demo took another victory lap. These days, Raw's viewership skews older, while plunging to new depths (the tune out in the latter likely aids the former).

It used to be that Monday nights were destination television for wrestling, but with Wednesday's combined AEW/NXT viewership total creeping up on Raw as Raw sinks, you wonder what WWE can do to right its flagship. Advertising matches in advance (like Randy Orton vs. Big Show) and trying to create post-PPV intrigue (Rey's eye and the Sasha/Asuka controversy) don't seem to be helping all that much.

Well here's a piece that might appeal to the 50+ demo: a look back at five extremely important matches in Raw's 27-and-a-half year history, each for their own reasons.

5. Razor Ramon Vs. The 123 Kid (1993)

The WWF tagline used to be, "Anything can happen in the World Wrestling Federation," and that proved to be the case in May of 1993. Young Sean Waltman was presented as an enhancement talent for weeks, getting soundly beaten by various midcard heels.

When he matched up with Razor, it appeared to be just another squash. That was, until Kid took advantage of a missed corner charge, then Moonsaulted onto Ramon to score the upset of the century. The match was a lesson to fans in not taking an outcome for granted.

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Justin Henry

Written by Justin Henry

In addition to writing lists and commentaries for Cultaholic, Justin is also a features writer and interviewer for Fighting Spirit Magazine, and is co-author of the WWE-related book Titan Screwed: Lost Smiles, Stunners, and Screwjobs.