Note that I’m not saying these are the best or most memorable moments of the year but rather the ones that I remember for one reason or another.
1993 – May 17 – The Kid b. Razor Ramon
We’re starting with a big one here as the show gave us a reason to buy the “anything can happen in the World Wrestling Federation” line. The Kid had wrestled a few squash losses under different names but came back here and beat a much bigger star completely clean with a moonsault press. This was the big shocking moment that made Raw feel like an important show, which hadn’t been the case up to this point. It was a game changer and the kind of match the show needed to really get going.
1994 – July 11 – Bret Hart b. 1-2-3 Kid
Again with the Kid. This one has been on a few home video releases over the years and it’s no surprise as to why. People were starting to get that the Kid was a rather talented wrestler and who better than to put him against that Hart himself? They had a great match and showed off how awesome they really could be. It was long, it was full of good action and for a split second I bought the Kid could win the title. Well done again here and a near classic match.
1995 – November 20 – Shawn Michaels vs. Owen Hart
You might be seeing Michaels’ name on here a lot and there’s good reason for that. Michaels and Hart had some crazy great chemistry together but this was much more about the ending. This was the match where Michaels collapsed near the end, which was shown on highlight reels for years. It set up Michaels’ return at the Royal Rumble and ultimately the boyhood dream coming true at “Wrestlemania XII”. Not bad for a twelve minute match which happened to be great at the same time.
1996 – January 1 – Raw Bowl
You don’t often see WWE mention football because it’s not going to be able to hang with “Monday Night Football”, but this time around WWE just went straight into a football themed match, complete with time outs and penalty flags. Sure it was stupid, but it was certainly memorable and that’s about all you’re going to get in 1996.
Yes this really happened.
1997 – September 22 – Cactus Jack b. HHH, Falls Count Anywhere
This is one of the best episodes the show has ever had with the show making its debut in Madison Square Garden and the first Stunner to Vince. However, there was another match on the show that had some long reaching implications of its own. Jack defeated HHH in one of the best brawls in the history of the show, which became the basis for a lot of the story at “Royal Rumble 2000”. Check this one out and then watch the rematch in 2000 as a bonus.
1998 – October 12, 1998 – Steve Austin Destroys Vince McMahon’s Corvette
Really, you could pick almost anything from Austin on this list (or the show after “Wrestlemania XIV” on its own with the debut of the new titles, the formation of the new DX and Austin vs. McMahon cranking into high gear) but I’ll take a personal favorite here. There’s something really cool about Austin driving some big piece of machinery and HE DESTROYED AN ACTUAL CORVETTE. That’s one of those things that you just don’t see them do (if nothing else for the cost) but this was Austin vs. McMahon at some of its craziest.
1999 – June 7 – Higher Power Revealed.
I remember watching this live and having my mind blown. Then I watched it again over fifteen years later and it was actually even better. The tension build up in the whole thing and the pacing at which everything came together was absolutely perfect with the first thirty minutes of that show being outstanding. The rest of the show is completely inconsequential but that first half hour is as compelling of a single segment as WWE has ever put together.
2000 – February 7 – HHH/Radicalz vs. Too Cool/Rikishi/Rock/Cactus Jack
This one isn’t so much about the wrestling because there’s very little wrestling to be seen. The majority of the match is pure chaos with a bunch of stories being thrown together for the sake of a huge match. The thing more than delivers and is a great spectacle with all ten guys working as hard as they could have. It’s a lot of fun and a great example of everything working so well at this point.
2001 – July 9 – The Alliance is Formed
Now this is one of those moments that was part of a horrible story but it blew my mind at the time. WCW going out of business was a big enough deal but then all of a sudden we have ECW joining in. Sure the ECW lineup was terrible but who cared? You had Vince vs. Shane and Stephanie with all three companies together at once. The reveal was amazing and all of this happened in one night, making it one of the most eventful episodes of the show ever. Again not good, but really entertaining.
2002 – February 18 – The Rock Challenges Hulk Hogan
I mean….what more do you want? This was one of the biggest dream matches in the history of wrestling and the match wound up delivering. However, the setup for the match was just amazing stuff with Rock squaring off with Hogan for the simple reason of he wanted to face the biggest name of all time. What more could you ask for? Well other than Hogan vs. Austin but take what you can get.
2003 – February 24 – The Rock Destroys Toronto
This should be played on a loop in promo class to show people how to work a crowd. Rock was the biggest face in the world coming in despite being a full on heel. Within about five minutes, he was about to be chased out of Canada with torches and pitchforks, all because he was one of the best talkers of all time. Rock mentioning Toronto, waiting a second for the face pop, and then ripping the fans apart for cheering their town being mentioned is nothing but glorious. It’s one of the best promos I’ve ever seen and pure mastery.
You need to see this.
2004 – December 6 – Lita b. Trish Stratus
Really, the match quality isn’t all that important here. It’s a good match for what it is, but this was the main event of the show. Not the last match and then the big segment or anything, but the match which was hyped up all night as the top story of the show. That was unthinkable for a women’s match until then and while it’s been topped since, this was the standard for a very long time. It really is the kind of trailblazing moment that paved the way for the future of the division, which you don’t get every day.
2005 – May 2 – Shawn Michaels b. Shelton Benjamin
It’s my favorite match of all time and one of the best free matches you’ll ever see. The idea here was very simple: take the former athletic freak and put him against the modern athletic freak with the idea that he’s facing himself from ten years ago. It made for one of the best matches in the history of “Monday Night Raw” and it still more than holds up to this day. If nothing else, Michaels superkicking him out of the air isn’t going to be forgotten for a long time.
2006 – January 9 – Edge and Lita’s Live Sex Celebration
I mean….what? This is one of those things where you’re told what happens and then you don’t know what to say. It was such an out there moment (complete with some inadvertent nudity on camera) and drew monster ratings. This felt like something different for a change and that’s what Edge needed to bring to his title reign. Of course it was over by the end of the month but my goodness what a start.
2007 – April 23 – Shawn Michaels b. John Cena
It’s one of the longest televised matches in wrestling history at over fifty five matches long (about thirty seven taking out commercials) and it turns out to be an incredible match. Cena looked like a star here but wound up losing to Sweet Chin Music in a rematch from “Wrestlemania XXIII” earlier in the month. As a bonus, this was on Cena’s 30th birthday, making it quite a present for him.
That’s a long one.
2008 – March 31 – Ric Flair’s Retirement Ceremony
I know he kind of ruined it later on, but Flair saying goodbye after all those years was a sight to behold. From the levels of talent in the ring with him to everyone getting to show up and send him off to the perfect song, it wasn’t missing much. It even brought a tear to my eye, which I mentioned to a buddy of mine who hadn’t see it yet. He kind of brushed it off, but then a few days later I got a text saying “you were right about Raw. I was bawling”. Throw in Undertaker and Vince McMahon showing up after the show was over and it couldn’t have been much better.
2009 – November 16 – Kofi Kingston Snaps
I’ve been a big Kofi Kingston fan for a long time and this might have been his crowning moment as a singles wrestler. After feuding with Randy Orton for months, Kingston finally snapped and beat the fire out of Orton, including a great brawl around Madison Square Garden. This should have sent him into the main event scene for good but alas it didn’t quite happen that way due to one reason or another (which may have been Orton being a jerk). Still though, it was great while it lasted.
2010 – June 7 – Nexus Debuts
The morning after this took place, I was talking to someone who said they had turned “Raw” off before the ending because nothing ever happens. He asked me how the show ended and I told him about the NXT rookies showing up and destroying everyone in sight, plus wrecking the set in one of the coolest endings to the show in years. His response: “I hate my life.”
2011 – October 31 – The Muppets Guest Star
I think that one speaks for itself but in case you don’t care for the Muppets (and I question your sanity), this was a very nice lighthearted show with things like Sheamus and Beaker being cousins, Miss Piggy vs. Vickie Guerrero (the fight I never knew I wanted until it happened) and some other great cameos in one of the only good guest star appearances.
I’ll never get over this.
2012 – July 23 – Raw 1000
I know we’re coming up on the 25th anniversary and that’s a big deal, but having 1000 episodes is quite an accomplishment as well. WWE pulled out all the stops here with Steve Austin, the Rock, Fozzie Bear, a wedding, Slick, Sean Mooney (some of these things might not be like the others) and it was as good as you would have expected. Of course it marked the shift to three hour show every week but you can’t have everything.
2013 – March 4 – Old School Raw
This had been done before but it wasn’t quite good enough to beat the Nexus debuting in 2010. If there’s one thing that WWE knows how to do, it’s plug the heck out of their history. That’s what they were doing here, complete with everything from the red, white and blue ropes to Lord Alfred Hayes setting up the commercials. It was a very fun show and that’s exactly what they were shooting for here.
2014 – April 7 – Shield Turns Face
You knew this was going to happen at some point but that doesn’t make it any less awesome. Shield had been teasing turning for a long time but it took a slip of Kane’s tongue to explain that he had actually ordered a beatdown of the team a few weeks ago. Shield came out at the end of the show to save Daniel Bryan from having his newly won World Title stolen from him by HHH. It was exactly what the fans wanted and that’s the way things need to go sometimes.
2015 – May 18 – Kevin Owens Debuts
Back in 1999, Chris Jericho debuted in a legendary segment with the Rock, showing that the company had big plans for Jericho. That was the case for another Canadian when Owens made his main roster debut and got to trade barbs with Cena. Owens came off like a star (“No, you don’t get to give me advice. I’ve been doing this longer than you have”.) and then he even went on to beat Cena in their first match. It was a star making performance and for once WWE actually followed through on the thing.
A star is born.
2016 – April 4 – Wyatt Family Teases Face Turn
This wasn’t the best year for “Monday Night Raw” but you can almost always go to the show after Wrestlemania for a quick fix. There’s a lot going on there but the Wyatts teasing their first face turn ever was a heck of something to look forward to. Unfortunately it never went anywhere due to Wyatt getting injured (and there’s no way they could try it again) but my goodness I was thrilled with this one.
2017 – April 3 – Roman Reigns Promo
Sometimes, all it takes is five words. This was the fallout from Reigns defeating Undertaker the previous night at “Wrestlemania XXXIII” and all Reigns said was “this is my yard now” before leaving. The key to the whole thing was the nearly fifteen minutes of pure hatred from the crowd, who booed Reigns out of the building for the sake of seeming retiring the Undertaker. It was simple, it was quick, and it did everything it needed to do.
Simply put, there has been a lot of good (and very bad) moments in the history of “Monday Night Raw” and hopefully you’ve gotten the chance to go back and enjoy some of them here. With everything available on the WWE Network, there’s more than enough to go back and watch, just for the fun of seeing some of the stuff you’ve forgotten. It’s a fun show, and history has shown that to be the case no matter how long it keeps going.
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