25 Best Moments in Raw History

Today, 22 Monday 2018, marks WWE’s celebration of the 25th anniversary of Monday Night Raw, the flagship cable show of World Wrestling Entertainment. As is usual with WWE, even the celebration date is a work – WWE’s first airing of Monday Night Raw took place on 11 January 1993 – as it allows them to use the 25th anniversary as the go-home for this year’s Royal Rumble which marks the unofficial start of Wrestlemania season.  As with all anniversaries such as these, it marks a perfect time to present my (personal) favorite 25 moments in Raw history.  I’ll try to do this with as little commentary as possible.

Also, just a side note, this is the non-Braun Strowman division because Strowman’s 2017 into 2018 is littered with potential top 25 moments. Everyone on this list should feel blessed that I didn’t count Strowman because he has been on a 98/99 Austin tear of equally big and ridiculous moments.

25. The Milk Bath, 20 August 2001

This makes the list as probably the best instance of “imitation being the sincerest form of flattery” that has ever happened in wrestling.  We’ll get to the inspiration for this moment later in this list, but just know that All-American Hero and Olympic Gold Medalist Kurt Angle stormed the ring in a milk truck and proceeded to spray the entire Alliance faction with honest to goodness milk.  Yes it was a ripoff of a previous angle, but it was so funny both because of the fact that it was a ripoff but also because the changes that they made were so spot on with Kurt’s character at the time.

24. Daniel Bryan Exits the Wyatt Family, 14 January 2014

This moment, while important, still sits in a weird space for me. It’s partially because I never understood why WWE even tried to put Bryan in the Wyatt Family in the first place.  We all wanted Bryan at Mania and this just seemed like it was going to be the detour that kept him from completing his story arc with The Authority. It’s also weird because it came out not long after this Raw that Bryan suffered a concussion.  Knowing what we know now about Bryan’s history of concussions and that he is still sidelined today because of those concussions, it’s hard to remember this as fondly.  Bryan famously commented after that he didn’t remember much of what happened in this segment.  Yea, that’s why this is so low on my list.

23. Nexus Tears Raw Apart, 7 June 2010

Most of these moments at the bottom of the top 25 are here because of things that surrounded the moment as much as the moment itself.  This moment suffers because WWE totally botched this storyline (stop me if you have heard that before) and because in the immediate aftermath of this episode Daniel Bryan was fired for actually choking Josh Matthews with his own tie.  This had every right to be a bigger deal in the long run than it ended up being but thanks to WWE shooting itself in the foot, this moment is just a reminder of what could have been.

22. Undertaker Crucifies Stone Cold, 7 December 1998

This moment serves as a reminder of just how “dark” WWE tried to be at times during the Attitude Era and specifically with The Undertaker’s character.  He hung Big Boss Man from the Hell in a Cell, tossed Mankind off of the same structure, I think he also crucified, or attempted to crucify Stephanie McMahon at some point.  So while this moment is important, it’s still a bit difficult to explain now.  Imagine 14 year old me trying to explain to my mom that it was no big deal that one man just tried to crucify another man Jesus-style on almost live tv.  Important, but weird, let’s move on.

21. Mark Henry’s Fake Retirement, 17 June 2013

This and the moment that follows are examples of times when WWE hits just the right sentimental or comedic note before switching into something meaningfully violent.  The violence here wasn’t quite as wild as in the next moment on this list, but it still seemed to be important in the moment (I say seemed and in the moment because it inevitably amounted to squat). Mark gives probably the promo of his life, in a salmon colored jacket no less.  He leaves a pair of his boots on the stage as he walks down to the ring (where John Cena is standing having asked for a new challenger after dispatching Ryback at the ppv the night before) He talks about respect, his path in WWE, so on and so forth. It’s all pretty sincere sounding stuff (so much so that I’m pretty sure he can’t even cut a retirement promo now because it wouldn’t top this) until Cena raises Mark’s hands and then goes to give him a respectful hug.  In that moment Mark scoops up Cena and hits him with the World’s Strongest Slam kickstarting a mini-feud over the WWE title.  The unfortunate component to this, of course, is that Mark failed to do anything with the mini-push and was quickly bumped down to more or less a gatekeeper for young big men since then.  This is particularly unfortunate because Mark was capable of going in the ring still and could have been a legit champion – plus given that speech, he sure as hell deserved a run.  But nope, to paraphrase Kanye West, “Vince McMahon hates black people.” So while it deserves a spot on my list, it can’t go too much higher than this and unfortunately doesn’t crack the top 20.

20. Festival of Friendship, 13 February 2017

Oh, what a display of malevolence.  There are more moments like this, ones that WWE slow burned almost to the point on insanity, but this one really teetered the line of taking too long to get to more than most.  We knew that the Jericho Kevin Owens partnership was not long for this world.  KO is a jerk and a selfish one at that (keep that in mind with the Royal Rumble handicap match that’s coming up in 10 days). There were so many moments prior to this one where it felt like the time was right to pull the trigger on this, but WWE kept meandering pushing along with this until the day before Valentine’s Day last year. Jericho puts together this Festival of Friendship that is almost like a 2017 take on Mankind’s “This is your life” segment with The Rock.  While it didn’t mirror the full scope of that segment, in my mind the spirit of the first part of the segment was the same.  The second part?  Well, while some people said they wished for a bit more violence, Kevin Owens did still systematically destroy Jericho.  He gave Jericho a list that had Jericho’s name on it.  The camera pulls back to show that it’s not the list of Jericho, but instead the list of KO.  At the exact moment that Jericho realizes what’s happening KO begins the brutalization.  Jericho gets smashed through the Jeritron, powerbombed on the ring apron and more or less beaten from pillar to post.  Owens released all of the frustration that his character had been holding for being partnered up with Jericho.  The sad part of this is obviously the fact that they used this as the mechanism to get the Universal Title of KO and setup Goldberg for a much telegraphed loss to Lesnar at last year’s Wrestlemania. It’s good to finally have KO back in a world title hunt even if it may be short-lived.  This in the moment was a segment well-earned.

19. Triple H Marries Stephanie McMahon, 29 November 1999

It’s amazing what 18 years can do to a wrestling moment.  At the time this was pretty funny to 15 year old me.  This little perfect bliss of Test and Stephanie was just ripe for ruining (rest in peace Andrew Martin) by the degenerates of Triple H and his buddies. (Sidebar: rule number one, never try to get married in a WWE ring, bad juju). Anyways, Test and Steph are all set for their wedding when H appears on the Titantron.  He says he has some footage and we are shown a video of an obviously drugged Stephanie riding in the passenger seat with Triple H in Vegas.  They roll up on a wedding chapel and tie the knot.  Steph is freaking out in the ring and everyone is pissed. Innocent Steph crying as she tries to shout “I hate you” is pretty classic stuff.  That this led to the eventually insufferable McMahon-Helmsley era does knock this down a few pegs, but it was still funny.  Focus on the “was”.  This segment does not pass the 2017/2018 smell test.  With everything that is happening in entertainment etc. WWE would be wise to bury some of their past, at least momentarily, because some of it really doesn’t look good on its current PG brand.

18. DX Invades WCW, 27 April 1998

If it wasn’t clear by now, it is going to become crystal clear shortly that I am a fan born and bred in the Attitude Era.  WWF/E between 1997 and 2001 is a treasured time in my mind.  So many of the E’s best moments took place during this time period. This moment, in the midst of the Monday Night Wars and before the tide swung WWE’s way forever, remains a standout for me just because of the “what ifs” that accompany it. What if Bischoff actually allowed WWE’s wrestlers into the arena that they were in?  What if these guys actually squared up with some of WCW’s top talent at the time? That question is particularly interesting because the top guys in WCW were all members of the Kliq from WWE or a part of their NWO faction.  This is fascinating for so many reasons.  Beyond all of that, it was also just dumb fun.

17. Shane McMahon takes over WCW, 26 March 2001

Much like number 18, this moment makes the list simply because of what actually happened and the possibility of what could have been. Fans already knew that WWE had purchased WCW at this point, that wasn’t news, what WWE wanted to make news was the (kayfabe) fact that Shane McMahon had bought WCW out from under Vince’s nose.  This eventually led to the much maligned Invasion angle of which the number 25 entry on this list is a part. It was epic to see a simultaneous broadcast of WCW and WWE with the Monday Night Wars so close in the rearview.  Despite the lack of proper follow-through and the poor idea of using WWE guys as members of the Alliance and not being able to lock down WCW’s biggest stars, this moment still stands the test of time because it was a legitimate “Holy Shit” moment towards the end of an era filled with them.

16. Seth Rollins Turns on The Shield, 2 June 2014

The most memed moment in recent wrestling history.  Any time a player moves on from a team, especially in the NBA, this is the go to meme.  This moment worked because unlike the slow burn approach of some of the other moments on this list, WWE just pulled a swerve on its audience.  Coming off their victories over a reformed Evolution, The Shield was riding about as high as any faction has in WWE history.  Then, Plan B.  Even though Seth’s explanations almost four years later still ring a little hollow, the magnitude of the fact that a) The Shield was breaking up and b) that it wasn’t hothead Dean Ambrose or hotshot waiting to happen Roman Reigns that initiated the breakup make this moment an unforgettable one.  The lack of a fully coherent reason from Seth keeps this from moving any higher, but the fact that this happened at the height of their run and so out of the blue makes it a definite top 25 moment. (Important note: always have a Plan B.)

15. Iron Mike Tyson vs Stone Cold Steve Austin, 19 January 1998

We get into the top 15 with a crossover moment that WWE will never let us forget.  Somehow WWE convinced Iron Mike Tyson to dabble in WWE for its Wrestlemania season in 1998.  His appearance on Raw was touted as a big deal, even as some of WWE’s commentators asked loudly “what might Stone Cold have to say about the so-called baddest man on the planet stepping into his ring?” Vince was in his glory gloating about such a coup while also doubling down to ensure that absolutely nothing went wrong with this big appearance. Long story short, Austin crashes the party making it clear that he and Tyson are on opposite sides.  Tyson goes on to side with Shawn Michaels as the build to Michaels vs Austin got heated leading up to that year’s Mania.  Eventually Mike reveals that he and Stone Cold were actually friends and he ensured that Austin wasn’t screwed out of his title opportunity on the grandest stage of them all.  In a lot of ways, this was a precursor to moments like Lesnar’s appearance at the Raw after Wrestlemania in 2012. Someone who was seen as a legitimate fighter making his presence known in WWE to the benefit of both sides.

14. Chris Jericho Debuts, 9 August 1999

Another personal favorite moment of mine. WWE had been teasing this Y2K countdown for weeks ahead of time but it was obvious that the countdown didn’t actually coincide with New Year’s Day 2000 but in fact it coincided with what was essentially just a random Monday in August of 1999.  The Rock comes out and is interrupted by the end of the countdown and the debut of Chris Jericho.  It’s important to  note that Jericho debuted interrupting The Rock who was arguably the hottest thing in Vince’s company at the time.  We were supposed to take him seriously and WWE wanted to show us that they took him seriously.  I somehow forgot this when Jericho beat Rock and Austin in the same night to become the first Undisputed WWF Champion a little over two years later. I didn’t understand in the moment why Jericho of all people would be given that sort of moment, but eventually I remembered that WWE was always high on him and it all ties back to his debut.  Given everything that Jericho has accomplished in his WWE career, it’s clear WWE was right about giving him this kind of debut.

13. Shawn Michaels vs John Cena, 23 April 2007

Holy Crap!  A few weeks after the epic bloodbath of their Wrestlemania 23 match, John Cena fought Shawn Michaels in a non-title rematch.  Matches like these were early signs that Cena could pull off great matches if given the right opponent.  This was also a reminder that Shawn Michaels is probably the greatest wrestler of all time. This match was a 60-minute instant classic and arguably one of the greatest Raw matches of all time. It had to make my list.

12. Shawn Michaels Loses His Smile, 13 February 1997

If you take away all of the backstage noise surrounding this promo (that being that Michaels wasn’t actually injured but just was not willing to drop the title to Bret Hart) it still stands as one of the best moments in Raw history.  It’s also one of the earliest promos that I remember watching as a wrestling fan.  Besides, when you add in the backstage noise and consider that this was a part of Michaels on and off screen war with Bret Hart and that this probably had a lot to do with Bret not wanting to drop the title to Shawn on his way out at Survivor Series late in the same year, this promo and this moment has a great deal of historical significance as well.

11. Austin Visits Vince in the Hospital, 5 October 1998

In all fairness, most of Austin’s antics between 1998 and 1999 tend to blur into one.  This moment along with the others captured on the list stands out as one of the more memorable ones.  Austin attacking Vince in the hospital has to be one of the best interactions between these two characters.  It was silly, it was fun, it was everything Vince’s brand of sports entertainment liked to be at that time. This moment represents most of the non beer bath Austin moments. You could group or replace this moment with Austin entering the arena in a Zamboni or Austin pouring concrete into Vince’s Corvette or The Rock tossing Stone Cold off a bridge and other such moments so this represents all of those moments on my list.

10. The Shield Turns Face,  17 March 2014

This is a top 10 for me for a number of reasons. First, fans were ready for this turn.  There is nothing like WWE slow burning just the right amount of time before making moves like this.  Much like other moments on this list, fans were clamoring to be able to fully cheer the heel faction since not long after their debut (that this was CM Punk’s idea is proof of his knack for pro wrestling). Second, and maybe this is just important to me as a hardcore fan, but the fact that the camera lingers just as they turn to face Kane resulting in quite possibly the most literal face turn in wrestling history, is just one of those neat attention to detail things that I enjoy. This registers a bit more for me than the disbanding moment and thus that is why this ranks higher on my list.

9. CM Punk Turns Heel (Raw 1000), 23 July 2012

Again, this is my list (yall know my stance).  This was a critical component of CM Punk’s WWE run.  First, he had called out “Dwayne” during his pipe bomb promo from just over a year earlier. Second, he was in the middle of what would be come the longest modern championship reign in WWE history.  Third, he was playing second fiddle to Cena before (and admittedly after) this night.  Fourth, it was Raw 1000.  This was billed as one of the most important Monday nights in the history of the program (much like how Raw 25 is being hyped – which mini tangent is great for The Miz who is likely regaining the IC title tonight) and CM Punk got to be featured in arguably the most important moment of the night.  Say what you will about how Punk was treated in this run (it was pretty shitty to be fair) but they at least tried to give him moments here and there. Plus, we’ll always have this glorious GTS on The Rock.

8. Brock Lesnar Returns to WWE, 2 April 2012

I’ll admit, I (fairly or unfairly) put this further down the list than I originally imagined I would.  It’s all because of what Brock has turned into in the years since this triumphant return.  Nonetheless, for me it’s a top 10 moment. This was around the time that I became a fool for internet WWE rumors.  The rumor mill was CONVINCED that Brock was showing up on this Raw after Mania.  At the start of this video, you can hear the crowd distinctly chanting for Brock, so for most people this wasn’t a surprise as much as it was the eager anticipation of a moment of catharsis. See at this point in Cena’s history, most smart fans were out on Cena.  It didn’t matter that he had taken the L to Punk and stepped out of the title scene because he was still main eventing ppvs over the WWE champ.  So we were primed to hear the beast’s music hit and watch him tear apart Cena. It was only one F5, but for most of us it was probably one of the most resonant F5s in history.  It’s amazing how in a lot of ways fan support has reversed for these two guys since, but in the moment, we were all the biggest fans of the return of the Next Big Thing.

7. Dolph Ziggler Cashes In, 8 April 2013

Ahhhh, the highest point of Dolph Ziggler’s WWE career. Two years after I dove back in to being a hardcore wrestling fan, this happened.  In the moment this was glorious.  Ziggler’s cash in was probably one of the most anticipated cash-ins of all time.  The minute Del Rio started grabbing his leg fans were ready for Ziggler’s music to hit.  That has to be one of the loudest pops in Raw history.  The best part was, WWE didn’t just run an automatic win, they actually made fans sweat for the victory.  Del Rio got Ziggler into the arm bar and we were all terrified that Dolph wasn’t going to win.  Then he punched at Del Rio’s foot forcing Del Rio to break the hold.  I literally remember standing up in my living room screaming “Zig Zag that nigga” at my TV screen as Dolph got ready to hit his finishing move.  I don’t know if other people will have this moment as high, and it’s sad that a concussion ended this reign prematurely and set Ziggler down the path to main event gatekeeper for most of his career since, but for me, it was an electric moment that was stiff competition to some of the moments in the top six.

6. Edge Retires from WWE, 11 April 2011

This, was a sad moment.  Quick history lesson, around this time in my WWE fandom I was off an on.  I watched the big four ppvs mostly and was tangentially following the week to week stuff.  I watched the Mania that happened prior to this night and had no idea this was coming.  All that being said, this still hit hard.  Edge was a legend to most Attitude Era fans.  He was a tag specialist, involved in the the first ever TLC match and at the time of my most fertile wrestling viewing, destined to be an IC title holder at most.  The fact that he became WWE champion and the perfect foil for John Cena was simply amazing in my eyes. That’s what makes this moment so memorable and so sad all at once.  It was probably the last retirement that no one really saw coming and Edge was probably the last guy who came up purely as a tag wrestler and elevated to a legitimate main event WWE champion and contender. Imagine what could have been if injury hadn’t cut his career short.

5. Mankind Wins the WWF Championship, 4 January 1999

This makes the top five for a number of critical reasons.  First, from a historical perspective, this marked the shift in the tide of the Monday Night Wars. Second, this was tied to a first in a series of bad decisions by WCW – having Tony Schiavone announce on Nitro that Mankind was going to win, followed by the infamous line of “That‘ll put a lot of butts in seats” was the beginning of the end of WCW. Third, this is an important reminder that back in the day, Raw was pre-taped and Nitro was live so the potential for cross company spoilers always existed. It’s surprising there wasn’t more subterfuge afoot. Also, Mankind won his first WWF Championship this night.  That tends to get lost in the shuffle of this particular moment.  Mankind was a journeyman at this stage of his career.  His quintessential career moment about six months before when he was tossed off of the Hell in a Cell by Undertaker, but nonetheless this first title (who cares that he won it with a LOT of help) solidified what he meant to business and confirmed his eventual legendary, Hall of Fame status.

4. The Beer  Bath, 22 March 1999

This is probably the most iconic Steve Austin moment on Raw.  Of course we have the King of the Ring promo and possibly his Wrestlemania double turn with Bret Hart as more important moments in his overall career, but as for Raw, this was tops.  I know most people may have this higher on their list, but for me, as a fan of many years it still doesn’t quite match up to the top 3. Nonetheless, this was one of the most fun moments to watch live that has ever happened on Raw over it’s 25 years.

3. This Is Your Life, 27 September 1999

Okay, six or seven years ago, this moment and the number 4 moment would have been 1 and 2 on the list, unfortunately for both, the number one and two spots hold very soft spots in the hear of this wrestling fan. All that aside, this is probably the all-time Raw moment for The Rock and quite possibly the best moment of his career.  This is known as the most watched segment in Raw history and given that altogether this segment was almost half of this episode of Raw, that’s a damn miracle.  Trying to get people to sit down through 30 to 45 minutes of a three hour Raw now is pretty much torture most Mondays. But this, this was an epic segment that was a perfect encapsulation of The Rock’s relationship with Mankind and the unbelievable chemistry the two had together. Damn, I miss the Rock and Sock Connection.

2. Occupy Raw, 10 March 2014

This was the moment that we knew for certain that Daniel Bryan would finally have a chance to truly have his moment at Wrestlemania.  After the pre-show match with Sheamus and then the 18-second match a year later, this was finally Bryan’s time to shine.  While this story started at the previous year’s Summerslam with a Randy Orton cash-in on Daniel Bryan who had just pinned John Cena clean, this was the pre-cursor to his Wrestlemania moment and we were all primed for it from this point forward. Damin, I miss Daniel Bryan in the ring. I still get goosebumps watching this and my obvious choice for number one…

1. The Pipe Bomb, 27 June 2011

There is not much that needs to be said about this.  Many of you may disagree, but I don’t care.  The pipe bomb is what drew me back into wrestling.  Without it I probably wouldn’t be writing this right now. It was the beginning of both CM Punk’s highest moments in WWE and the end of his time in WWE all in one.  It encapsulates the best of what wrestling could be – a wrestler who was great in the ring and on the mic with a legitimate beef, an expiring contract and the freedom (work or shoot) to talk about it on a live mic in the main event segment of the company’s flagship show. Damn, I miss CM Punk.

Do you agree with my list (probably not)?  Post your thoughts on 10th Year Seniors on Facebook.