Fightful Staff Choose Their Favorite Monday Night Raw Moments

Tonight, Monday Night Raw celebrates its 25th anniversary.

Blending the idea of Memphis style studio wrestling with the pizzazz of WWE and their larger than life superstars, bringing wrestling to a live weekly audience on a cable network was, at the very least, a pretty interesting idea to explore. Would it work, or would it falter? 

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As the years went by, that answer became clear. Raw morphed into a ratings juggernaut at the height of the Monday Night Wars, establishing some of the most memorable pro wrestling characters of our time. Even to this day, it continues to be one of the most important and influential pro wrestling programs anywhere, and throughout the years has become a barometer for any wrestler's success in North America.

Yes, people will be quick to point out that week to week, Raw can be a chore to get through sometimes. Three hours is long. We've all complained about something every once in a while, for good reasons or not. But when something good happens on Raw, it's really good. Even today, there are segments out there that affirm our reasons to keep watching, even if the show sometimes may take us to new lows of interest.

Fightful Staff have come together to share their own favorite moments throughout Raw's history. Check on the next page to see what moments made our list.


Ric Flair's Farewell Address
Raw #775
March 30, 2008

Over its now 25 year existence, Monday Night RAW has been graced by many legends, but few come with the kind of legacy and history that Ric Flair does. It was March 30th, 2008 and Flair was just one night removed from his iconic WrestleMania retirement match with Shawn Michaels. This would be Flair’s official farewell address, and just as you’d expect, it proved to be a fitting tribute for ‘The Nature Boy.’ After a brief in-ring promo, Flair’s music hit. But before he could depart, Triple H arrived to pay tribute to his old friend.

This made Ric cry immediately, because of course it did, and Helmsley wasn’t alone, introducing a bevy of Flair’s peers who were also here to celebrate his great career. The Four Horsemen, Dave Batista, Ricky Steamboat, Harley Race, Shawn Michaels and many others would make their way down to the ring for a warm embrace with the legendary Flair and soon the whole roster followed, filling up the ramp proudly. After RAW went off the air, even The Undertaker appeared in a moment symbolic of Flair’s immense impact and importance.

Ric Flair may not have exactly left the memories alone so to speak, but this moment is still unmovable as one of RAW’s absolute finest.

- Joe Hulbert


Shawn Michaels vs. Shelton Benjamin
Raw #623
May 2, 2005

A personal favorite of mine was Shelton Benajmin vs. Shawn Michaels from 2005. It's funny, because if you were to ask me three matches that really stick out to me as Raw favorites, all three involve Michaels. Benjamin, Cena in the UK, and Triple H on the last Raw of 2003 really underscore how impressive Michaels was in his final WWE run.

As for Shelton Benjamin, he was my favorite performer to watch in the 2000s. I always thought he had some special intangible in the ring that made him connect to any main event level guy he worked with -- HBK, Triple H, The Undertaker, Christian, Chris Chris Jericho, Jeff Hardy, RVD, Orton. He delivered with all of them.

Shawn Michaels made Shelton Benjamin in 2005, the way that Triple H made Shelton in 2004, and the way that Kurt Angle tried in 2003 with Team Angle. The next week following the bout, I was expecting a major push to start for Benjamin, but it never did. Fortunately, the match lives on with the adoration it deserves as one of the greatest in Raw history. Two of the best in-ring guys of that era giving it all at a time when steroids and mic skills were far more important to many than in-ring ability.

People can tell me Shelton Benjamin didn't have "it" all they want, but his facial expression when Shawn Michaels' music hit told a story that was echoing throughout my living room. His work with Vince McMahon and Trish Stratus was a lot of fun, too. 

- Sean Ross Sapp

Raw Goes On Strike
Raw #959
October 10, 2011

This may be one of the most underrated moments in Raw history, but it's certainly my favorite moment.

Back in 2011, I was slowly getting acclimated with WWE. For years, I only got to watch SmackDown in Spanish, but didn’t really pay too much attention. When I tuned in to RAW on that October night, I was expecting to see the opening promo and see what the main storyline would be. Instead, we saw Triple H, CM Punk, John Cena and Sheamus give out a passionate promo about staying in WWE through thick and thin.

We then saw Cena and Sheamus have a match with Triple H as the referee and Punk on commentary in what was the most bizarre opening to Raw that I can remember. Combine that bizarreness with Punk’s comedic quips as an announcer and towards Triple H and you have my favorite RAW moment of all time, which also began the long reign of John Laurinaitis as the new GM of RAW. Truly a weirdly amazing segment on RAW.

-Carlos Toro

There are a lot of great moments that have happened over the past 25 years on WWE, so here are my personal top three (in no particular order):

Steve Austin & The Undertaker vs. Mankind & Kane - Hell In A Cell Match
Raw #254
June 15, 1998

Although it was an angle more than a match, the brutality and violence of the first Hell In A Cell Match on free teleision was awesome. Plus, that pop Austin got when he climbed the cell to go after Kane was awesome.

Lita Almost Breaks Her Neck
Raw #602
December 6, 2004

Lita returns from an extended absence after a neck injury to become one of the first female superstars (along with Trish Stratus) to main event Raw. What I will always remember the most is Lita landing awkwardly on her head during a dive outside the ring and looking like she had injured her neck all over again.

Edge Retires
Raw #933
April 11, 2011

Edge ranks in my top ten favorite pro wrestlers list, and even though I was working as a writer already with some insider knowledge of the business, I had no idea this was going to happen. This was a true shocker, but in the end of the day and with every wrestler who has suffered life altering injuries, I would rather see them retired and healthy instead of crippled and destroyed. 

- David Tees

Shawn Michaels vs. John Cena
Raw #726
April 23, 2007

Shawn Michaels is without a doubt one of my favorite wrestlers of all time. He'd probably be many people's favorite if you ask around. Hell, most of the moments on here involve the Heartbreak Kid in some form or fashion. But one moment in his long, illustrious career stood out to me as being something special, something that hasn't been done much on Raw since and may never happen again, or at the very least won't be as good.

John Cena and Shawn Michaels faced off against each other on the April 23, 2007 edition of Raw. It was a rematch from their recent WrestleMania 22 match, which was also pretty great. It wasn’t just that they wrestled for 55 minutes -- the beauty of it all is that not one time was it ever indicated it would go this long, unlike almost every other match of its length in WWE history. And that’s what made it special.

It was a slow and deliberately paced match, so expert wrestling fans might have assumed they were going to go a long while. But what I loved about this match, watching it again almost 11 years later, was that everything felt important. This wasn’t your normal WWE style match of today where you have to go for a submission or rest hold because you've been instructed to work a slow pace.

This wasn't a modern day "WWE match", or the kind of match they've patterned as of late. This felt like a fight; a battle between two guys where the goal was to prove who was better. That seems so rare nowadays, where epic main event bouts are more about who can come up with the flashiest moves or counters. Not that it’s the wrong thing to do or anything -- that style works too. But whereas those feel like great contests, this felt like a fight.

This moment, like many others, highlight how cool an episode of Raw can be sometimes. You never truly know what will happen, how it will be executed or how the fans will react. The fun of watching Raw is getting a wildly unpredictable moment you never saw coming. This match in particular isn't everyone’s first choice when it comes to a wild moment in Raw’s history, but it certainly hits all the right checkmarks in my book.

- Bryan Rose

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