Well we are about to reach the 25th year since WWE’s flagship show, Monday Night Raw, first aired.
Now if you know me well enough, you will know I have been a huge wrestling fan for over 30 years now and I can truthfully say I have been watching Monday Night Raw since day one. There have been some many memorable and fantastic moments, throughout this shows 25-year history, that it was hard to narrow it down to just 25 moments.
However, I decided to make it easy for myself and pick MY personal favourite moments of all time. Now, that means important moments like, Foley wining the title, DX invading WCW, Shane buying WCW, Eric Bischoff hugging Vince etc., are not on my list. It isn’t that I don’t love those moments, its just that they are not my personal favourite moments. If I was making a list of the 25 most important or memorable moments on Raw, this list might be a bit different, but this is a list about me.
I encourage everyone to post their own personal lists as well and join in on the fun. I will provide the YouTube link for each moment.
- Mark Henry’s “Retirement” Speech
In what I consider to the be the most underrated moment in Raw history, the WWE was able to trick even the cleverest of its fan base, when they started to have Mark Henry tweet over a weekend period, that he was going to announce his retirement on that Monday’s Raw. Henry came out after a John Cena promo and started his speech asking John to stay in the ring. After a brilliant speech, where he thanked Cena, the fans, the WWE and his wife and kids, with REAL tears he officially announced his retirement. He then hugged Cena, only to STUNNING turn that hug into a World’s Greatest slam! IT WAS ALL A HEEL turn! It was an Oscar worthy speech from Henry and one of the great shockers of Raw history.
- The Old Stone Cold come back to Safe WWE. July 16 2001
The Alliance of former WCW and ECW members, was threatening to take over the WWE and invade Raw. Vince McMahon was begging, the now silly and corporate Austin, to turn back into the old Stone Cold and whoop some ass. Austin refused. So, on that weeks Raw, we saw Austin at a bar with his wife instead of at the arena. Vince tried one more time to get Austin to come back and he refused. That is till he saw footage of The Undertaker and Freddie Blassie, riling up the troops. Austin snapped and smashed a pool cue and drive off to the arena. When he got there the Alliance members were attacking the WWE guys in the parking lot, backstage and in the ring. Austin came out and started whooping ass in the parking lot, followed by the backstage area. Finally, the glass broke, and Austin came storming out and giving Stunners to everyone who was moving. I loved this moment so much, because it was during a time I had stopped watching wrestling and I just happened to watch that week. I damn near brought me back into the fold.
- Bret Hart Snaps March. 17 1997
This was the first OMG moment I can remember on Monday Night Raw, that wasn’t about a surprise win. Bret Hart, after being screwed at the Royal Rumble, in a title match with Sid and on that weeks Raw in a Steel Cage rematch with Sid, had finally had enough. Vince came in the ring to interview Bret, who then shoved him to the ground and said, “THIS IS BULLSHIT!” It was shocking as hell coming from the usually mega baby face Bret and the PG WWE. Bret would go on to have a 10-minute rant, about how he was tired of being screwed over and the WWE doing nothing about it. I remember watching this when I was 13 and thinking WOW, this is crazy! It was shocking and a sign of things about to come for the WWE.
- Test and Stephanie’s Wedding Nov. 29, 1999
We all know the golden rule about WWE weddings and this one was no different. At first, what seemed like it might be the wedding to break that rule, Test and Steph had a nearly flawless wedding and were about to say the I Do’s. Then Triple H appeared and showed the world a video. The video is of him taking a drunk and passed out Steph, to a drive through wedding chapel and marring her! Triple H was just excellent in this video, speaking for the out cold Steph and over acting about being married. It was the first time, where you truly saw how much of a bad ass heel Triple H really was and the first time I thought damn, this guy is a star!
- HBK’s Retirement Speech March. 29 2010
I was there live in attendance for this one and considering that HBK is my all-time fav in ring performer, this was a moment that will forever be special for me. HBK had lost his match with The Undertaker the night before at WM 26 and with it he lost his career. HBK came out and instead of a flashy huge goodbye (see lower on this list) HBK decided to go the low-key route. He came out and thanked his fans, friends, family and WWE. Triple H appeared to send him off and before HBK even said a word The Undertaker came out and tilted his hat at HBK. I may have wanted that big huge flashy goodbye, but looking back on it now, that was about the perfect way for HBK to ride off into the sunset. I was very happy to be there live.
- Austin Stuns McMahon for the first time Sept. 22, 1997
They had been leading up to it for weeks and the fans were badly wanting to see it finally happen and the timing was perfect. Austin had been stunning everyone, from Jim Ross, to Sgt Slaughter to The King Jerry Lawler and everybody knew, there was only one more major name left on the list. The owner of the WWE, Vince J McMahon. Austin had come out and cause all kinds of hell that week and a pissed off Vince got in the ring and was about to have him arrested. The crowd was going crazy at what we all knew was about to happen! Finally, Austin kicks McMahon in the gut and lands a Stone Cold Stunner on the boss…the worst looking Stone Cold stunner ever, as Vince sold it horribly! The crowed went nuts, I went nuts at home and Austin got arrested. It was brilliant and as a massive Austin fan, a moment I will always love.
- The Black Wedding April 26, 1999
I have so much personal love for this moment! During the previous nights Backlash PPV, The Undertaker and his Ministry, had kidnapped Vince’s daughter Stephanie and was going to force her to marry The Undertaker. Taker said he can have her back, in exchange for control of the company. Vince was pleading with everyone in the back to help him, including his mega arch enemy Stone Cold, who refused. Taker and his goons had Steph in the ring and tied to a cross about to make the marriage official. Ken Shamrock ran to the ring and was taken out by Taker’s hit men. Next the Big Show ran out but was taken out by Taker himself. The tension was rising and the marriage almost official, when FINALLY, the glass breaks and Austin comes marching out! He takes out everyone on his way to the ring, as a young Davefather is going positively insane at his house! They just built this thing up perfectly and the pay off was brilliant! If you had asked me as child, what my fav Raw moment was, there is a good chance this would have been the answer.
- Live Sex Celebration Jan. 9, 2006
In, one of the WWE’s last memorable, over the top segments, before we moved into the PG era, Edge and Lita, decided to have live sex, in the middle of the ring, in front of the live crowd! Everyone who wasn’t watching their first Monday Night Raw, knew that Edge’s rival Cena was going to come out and stop the whole thing. However, what none of us were expecting, was how far Edge and Lita would get, before Cena appeared, well first Ric Flair. Lita was stripped to her bra and panties and Edge to his boxers, with a very clear boner. That got under the sheets, were Lita took off the bra and we got a nip slip! They were just about to start fooling around, when Flair finally came out and made the save. Edge destroyed him and finally Cena arrived. This was a very edgy segment and the one that I believe, finally pushed to far and forced the WWE’s hand to go PG. Still it was brilliant and one of the few moments from that era of WWE, that really stands out to me.
- Hart Foundation Forms March 31, 1997
Speaking of underrated moments in Raw history, how about this classic that most people seem to forget. The British Bulldog and Owen Hart, who were a tag team at the time, were clearly in the middle of what seemed like a break up angle. On this Raw, it looked like the WWE was about to pull the trigger and make the split. Owen and Davey Boy were in the ring, pushing and yelling at each other and just beating the hell out of each other in a match, when suddenly the freshly turned heel Bret Hart, came running out. He started asking the brother in laws why they were fighting, for these loser fans and that this is exactly what the American fans wanted. All 3 of them hugged and The Hart Foundation (one of WWE’s most brilliant factions) was formed. What makes this segment so brilliant was Bret Hart. His work as a heel was just getting started but he had already nailed it down pack. The way he looks smugly at the crowd, while in the middle of the group hug, was a stroke of brilliance and further proves why Bret Hart was the greatest in ring psychologist of all time.
- The Shield Breaks Up June 2, 2014
The Shield was one of the all time great creations the WWE has ever come up with. Taking 3 studs from NXT and having them form a unit, that ran destruction across the WWE, while having great matches, week in and week out. The Shield had just beaten Evolution at the Payback PPV the night before and were in the ring celebrating. Triple H came out to cut them off and slyly tell them to stop celebrating because he always has a plan B. It was at that moment that Seth Rollins took a steel chair and smashed it into Roman Reigns back. A shocked Dean Ambrose looked on, until Seth smashed him with the same chair. The reason this break up was able to stand out so much, was not only because it was the break up of a group, nobody was done with yet (for once the WWE, hadn’t waited to long!) but because they took the most unlikely member, in Seth Rollins and turned him heel against the group. That simple choice, made sure that this was destining to be one of the all time great Raw moments.
- Ric Flair’s Retirement March 31, 2008
Now had slick Ric managed to stay retired, this moment would have likely ranked a lot higher, but because he wrestled again, outside the WWE, this moment has lost some of its brilliance. Still, that said, this was easily one of the most emotional and brilliant moments in the history of Raw. The WWE made sure to go all out for one of the greatest to ever step in the ring. Ric was able to come out and say his piece, to his fans and family. Then it was time for his WWE family to show him some respect. Triple H came out and started a parade of influential figures in Ric’s career, including HBK, Ricky Steamboat, The 4 Horsemen, Harley Race and Batista. Then, the entire locker room cleared out. They allowed Ric to do some of his signature moments, like drop some elbows on his jacket and they went off the air, with an emotional Ric balling his eyes out. However, it didn’t stop there! An online only clip showed, both The Undertaker and Vince himself coming out, to thank and congratulate Ric Flair. It was a damn near perfect moment and the best sent off you will ever see in the WWE. To bad Ric had to tarnish it a bit.
- Chris Jericho Debuts Aug 9, 1999
Now I know that a lot of people would either have this in their Top 10 or as their #1. As much as I love the moment, I am kind of in agreement with Jericho himself, that it got a bit cheesy at parts and is really dated now. However, all the rambling with The Rock a side, the crowd pop and the first few moments of this debut, are legendary. For weeks the WWE had set up a Millennium count down clock. Of course, some clever wrestling fans, would figure out that this clock didn’t reach the millennium. So, on this edition of Raw, right when The Rock was in the ring, mid way though one of this promo, the clock was about to reach zero. The crowd was going insane, it was electrifying listening to them. It finally hits zero and we get a big boom, followed by something on the titan tron. Then the words JERICHO appeared and the crowed went NUTS! There stood Jericho, with his back to the crowd and his arms stretched out, he finally says, “WELCOME TO RAW IS JERICHO!”. The rest is history! Jericho to me, was one of the few WCW guys who I was very familiar with, so him coming to the WWE was a huge deal. Jericho would go on to be one of my all time favourite wrestlers and his debut is still a topic, amongst my STUPID idiot friends!
- Festival of Friendship Feb 13, 2017
Chris Jericho was having the run of his career with his new gimmick, where he put people on his list and called everyone stupid idiots. He was also in a partnership with then Universal Champ Kevin Owens. Together then had spend 6 months, causing chaos on Monday Night Raw and had started to get the fan support, despite being heels. So, Jericho, decided that to celebrate their great friendship, he was going to hold a festival, in honor of it. This laugh so hard you cry segment, saw Jericho giving Kevin Owens a whole host of strange gifts, which even included Gillberg (as Owens was feuding with Goldberg at the time), who Owens beat the crap out of. Finally, Kevin decided to give Chris, his gift. Jericho opens the box and sees a new list and is excited. As he pulls the list out of the box, he asks why his name is on the list and the camera pans to the back of the list, which reads, The List of Owens. Jericho looks at the back and suddenly realizes what is happening, as Owens attacks and destroys him, including tossing him through the Jeri-a-Tron. This was a brilliant way to end a brilliant storyline and set up their WM match that year. It was funny, and it was sad, all thanks to Jericho, who was in top form that night.
- Pillman’s Got a Gun Nov 4, 1996
It was the moment that the WWE, maybe went to far, but I will be god damned, if that wasn’t one of the most shocking and memorable moments in WWE history. Austin had broken Brain Pillman’s leg the weeks before and making it so that Pillman, couldn’t be at the arena for that Raw. So, they decided to send a camera crew over to Pillman’s house, to record an interview. During the interview, you hear a concerned voice, yell out, he is here! The he is being Stone Cold, who had made his way to Pillman’s house and was trying to break in. We go to a shot of the back door and Austin trying to push his way through, followed by a quick shot back to Pillman, who is now pointing a gun at Austin! There is a struggle and we hear a gun shot and the camera drops its feed. This was the moment that got the WWE a ton of heat and backlash. They had to apologize for it and pay a fine. However, like myself, any wrestling fan watching live that week, thought it was one of the best Raw moments of all time.
- Bret Screws Bret Nov 17, 1997
The Montreal Screwjob, is one of the most infamous moments in wrestling history. It was where Vince McMahon, with the help of Triple H and HBK, had decided to legit screw Bret Hart over, at the Survivor Series PPV, to make sure the WCW bound Bret, didn’t take the title with him, when he left. This lead to Bret punching Vince in the face, for real in the back after the incident. Jim Ross had a sit down interview with Vince lined up to discus this incident, on this edition of Raw. Vince, with the shiner on his eye still very visible, discussed what happened. He would then say the now infamous line, that many believe was the official start of both the Mr. McMahon character and the attitude era. “ Bret screwed Bret”. It was brilliant in its simplicity, a line that would live on forever and be quoted by wrestling fans forever, including myself.
- Occupy Raw March 10, 2014
Daniel Bryan was one of the few, wrestlers who worked in the indies, who I was aware of. So, when he came to WWE, I was excited as could be. I was even more excited, when he finally started getting over with the crowds. Of, course the WWE had to not listen and shove something we were not interested in, down our throats. Well the fans had, had enough and decided to fight back. We started hijacking WWE shows, chanting Bryan’s YES chant at every show, crapping all over Batista winning the Rumble when we wanted Bryan and even forcing Bryan to turn back face, after a misguided heel turn (see below). So, on this Raw, the WWE used this popularity to right a wrong. Daniel Bryan came to the ring and refused to leave until he was giving a match with Triple H at WM. He even brought in a bunch of fans, where Bryan’s shirt, to cover the ring. Finally, a brilliant Triple H comes out and expects the match. Bryan says, well that is not good enough, and demands that if he beats Triple H at WM, he gets inserted into the main event later that night. A furious Triple H, tries to rush the ring but is stopped by security and accepts Bryan’s offer. This was one of the most perfect moments in WWE history. Triple as I said was just top notch here and Bryan was every bit as good. Seeing, the image of all those Bryan fans in the ring, was one of the few moments I can honestly say I was jealous, of not being a part of.
- Nexus Debut June 7 2010
By the time, 2010 had come around, I had been a wrestling fan for almost 30 years and it truly took a lot to really getting me excited for something, happening on Raw. So, on this raw, there was a main even match between CM Punk (during his mask wearing gimmick) and John Cena. As the match was about to end, Wade Barrett, the winner of NXT, started to come down the ramp. Next thing you know, the ring is being surrounded by the rest of the NXT cast, which included Daniel Bryan, Ryback and Heath Slater. The NXT group jumped in the ring and started to destroy Cena and Punk. They then destroyed the ring, beat up the ring announcers (an act that would get Daniel Bryan fired, temporarily) and just cause havoc everywhere. It was one of the biggest holy shit moments, in Raw history! Even I, a hardened veteran fan, was in total shock and thinking, wow that was one hell of a brilliant moment.
- Kurt Angle Milk Truck Aug 20, 2001
We all know that the Austin Beer truck, was one of the most classic and best Raw moments of all time (just look below!), so it was a stroke of complete genius, when the WWE, had Kurt Angle remake the moment, only this time, with his signature drink of choice, milk! Angle was feuding with the then heel Austin. While, in the ring with his Alliance members, Kurt Angle came driving down the ramp in a milk truck! He started to throw milk cartons at them, the way Austin would toss around beers. Then he grabbed a hose and started to spray everyone with milk! The complete the brilliance Angle then stood a top of the milk truck and started to chug milk, the way Austin chugs beers. It was funny and a complete act of brilliance. I wasn’t even watching live at this stage, but as soon as I heard about it, I had to look it up!
- Bret Hart and HBK bury the Hatchet Jan 4, 2010
The long time feud between bitter rivals Bret Hart and HBK, was one that really had a lot of personal meaning to me. It was the basis of a real life feud between one of my best friends Talha and I. He was a massive Bret fan and I was a massive HBK fan, and even though we each respected the others favorite, it was still awkward at times for us to talk about. So, when it was announced that Bret Hart would be returning to the Jan. 4, 2010 Monday night Raw (my birthday), it was must watch TV. Bret comes out and the first thing he does is call out HBK! I was like OMG, just going insane and texting Talha! When they both got into the ring and finally shook hands and then hugged, I got the biggest chill down my spine! It felt like the weight of the world had been lifted off my shoulders, let alone Bret and HBK’s! It was a moment that both Talha and myself had dreamed off for years and there it was finally happening! A moment I can never ever forget!
- 1-2-3 Kid beats Razor May 17, 1993
In what would be the first brilliant moment of Monday Night Raw history, we saw the unthinkable happen. Razor Roman, one of the WWE’s top heels at the time was having a match, with one of the WWE’s jobbers of the time, named the 1-2-3 Kid, a skinny high flyer, wearing blue tights. Razor was being cocky during the match, dusting his hands, and taking his time to make pin covers. Razor tosses the Kid into the ring post and goes in for an elbow smash but misses. The Kid jumps up on the top rope and does a moonsault right onto Razor, pinning him for the 1-2-3! This was a great holy shit moment for everyone watching. I was watching this live with a friend and we were marking out like crazy! It was just a memorable moment that has stood the test of time.
- Austin Beer Truck March 22, 1999
Considered by many to be the best moment in the history of Monday Night Raw, I have a ton of love for it as well, as you can see, but there are 4 moments I simply love more. This was epic for its time though and watching live as a young teenager, I thought this was the coolest thing ever! The Rock, Vince and Shane are all in the ring cutting a promo. We had see before the commercial break, Austin talking to the beer truck driver, so we knew something was up. Mid way through Rock’s promo, the glass breaks and out comes Austin driving the beer truck! The truck damn near, collapses the Titan Tron! Austin gets on top of the Beer truck and starts cutting a promo on The Rock. Suddenly, Austin has a hose and starts to spray everyone in the ring with beer! This leading to the classic moment of Vince McMahon swimming in the beer! This was at the peek of my Stone Cold obsession and this moment was just a classic for me.
- Daniel Bryan turns on the Wyatt Family Jan 13, 2014
This moment has an image that is forever burned into my head, making it one of my favourite moments in WWE history. The WWE was doing everything it could to cool the popularity of Daniel Bryan, even forcing him to join the Wyatt Family. Yet it didn’t matter, because the audience wanted to cheer for Bryan and that is what they did. So, on this Raw after a steel cage match that Wyatt lost, he was in the ring trying to humiliate Bryan. He goes to put Bryan in the Sister Abagail and Bryan pushes Wyatt away. The crowd is going INSANE! Chanting YES and Daniel Bryan. Wyatt goes to attack Bryan and he moves out the way and hits Bray with a series of flying drop kicks. The crowd is just losing their mind at this point! Bryan does a bunch of YES kicks and takes care of Harper and Rowan, the other Wyatt members on the outside. He then goes into the corner and starts a YES chant…. every single person in the crowd, is doing it in unison! Bryan finishes off Bray and goes to the top of the cage and does the YES chant some more with the crowd right there with him. It was just an epic moment! I literally had goosebumps watching it then and I had goosebumps watching it again for this list.
- HBK’s Montreal Promo Aug 15, 2005
Shawn Michaels is without question the greatest in ring performer in the history of WWE. However, what most people don’t remember about HBK, is how good he was on the mic. There is no better example of this, then when HBK was in Montreal. This was during the brief stint, where HBK turned heel to face Hulk Hogan, at the Summer Slam 05 event. Being that it was Montreal and the Canadian fans had still not forgiven HBK, for his involvement in the Montreal Screw Job, the crowd was RED HOT that night, booing HBK out of the building. However, HBK was in full control of that crowd and having them eat out of the palm of his hand. HBK starts singing his own version of the Canadian National Anthem, egging them on about Bret and the Screw Job. Then Bret’s music hits!!! HBK looked terrified! The building was going insane!!! I was watching at home and I was losing my mind! Then nobody comes out and HBK starts laughing at the crowd! It was as stroke of brilliance! He then goes on to trash Hogan and then Hogan’s music plays, who we know was in the building. But once again HBK was playing with our hearts. The promo goes on with Shawn being booed worst than anyone in history. At one point he sits in the ring and waits for the crowd to calm down. It was just all around brilliant and one of the Top 3 greatest promo’s in WWE history.
- CM Punk drops a Pipe Bomb June 27, 2011
Speaking of all time great promo’s in WWE history, here is what I consider to be the all time best. John Cena had just had a match and lost thanks to CM Punk interfering. Punk, wearing a Stone Cold shirt, then sits on top of the ramp and starts to let lose. At first, he starts talking about why he dislikes John Cena so much. Then Punk just starts to let lose. He starts telling it exactly how he feels, in real life, including how he is tired of not being pushed because of guys like Cena, who just kiss Vince’s ass. He then talks about how much he hates Dwayne (The Rock), breaking the 4th Wall, being the best in the world, being a Paul Heyman guy, imagery brass rings, how he isn’t on any merchandise, not headlining WM, the fans selling autographed stuff on Ebay, New Japan, ROH, how Vince isn’t a billionaire because he hangs around “yes” man, how Vince’s idiotic daughter and doofus son in law are the reason why this company will still suck when Vince dies. His mic is then cut off. My jaw was on the floor! We had never heard a promo like this ever! It was totally shocking and brilliant beyond words. The fact that Punk did this all, while sitting on the top of the ramp, with his legs crossed. The reactions from other wrestlers and fans, was off the charts. This was a moment that was an instant classic moment, and everybody knew it.
- Brock Lesnar Returns April 2, 2012
I may be a bit biased, because I was there live for this moment, but there is no question in my mind, that this was my favourite moment in the 25 year history of Monday Night Raw. It was the Raw after WM 28 and the crowd was red hot, like no crowd I have ever been a part of before. We were busy putting Daniel Bryan over all night long, chanting YES! YES! YES! It was just electrifying being part of that crowd and by the time Cena had come out, I was already declaring it one of the best live events I have ever attended. Cena who had just lost to The Rock the night before, was cutting a promo on him and he finally calls him out. We get a pause, waiting for someone other then the Rock to come out, because we all knew he wasn’t there. We were expecting Cena’s next feud, from one of the boys in the back. Then came the familiar sound, we hadn’t heard in 7 years. Brock Lesnar comes out! I am telling you and I am getting goosebumps just typing this, that crowd reaction was one of the loudest things I have ever heard! It was massive! Everyone, including me was losing their minds! Brock then comes down and takes out Cena and my god, what a moment it was. As a fan, that is my all time fav moment, because I was there live, and it was so damn brilliant! No moment from Raw can even come close to touching that for me.