June 12, 2024

The Best Moments in WWE Monday Night Raw History

Tonight, WWE’s Monday Night Raw will celebrate its 25th anniversary. Over the course of that quarter century, viewers have been treated to some unforgettable moments, both good and bad (Mae Young’s birthing of a hand, anyone?). It’s clear, though, that WWE’s flagship show was a groundbreaking achievement in television, wrestling or otherwise.

To help celebrate Raw’s 25th anniversary, the Tailgate Society has once again brought together their pro wrestling contributors to discuss the Top 5 Moments in Raw History. From the Attitude Era to present day, Jason Mitchell, Brad LaFratte and J.T. Nutt come together to give their own personal highlights from the show that helped shape the wrestling landscape.

Jason Mitchell (@JMitchellTGS)

1. DX Invades WCW Monday Nitro

April 27, 1998

When I think back to the Attitude Era of the WWE, this is the moment that is crystallized in my brain. At the height of the Monday Night Wars between Raw and Nitro, the most bombastic blow was struck when, in a move that us basically unrivaled in pro wrestling history, Degeneration X stormed enemy territory. This was a time when fans were on the edge of their seat waiting to see who the next superstar to jump promotions would be. But to see Triple H and X-Pac driving a jeep and holding assault rifles right outside of the arena where Nitro was being held yelling “Let my people go” (referring to their friends Hall and Nash) was insane. Maybe the boldest move by either company during the Monday Night Wars. While not the blow that killed WCW, it was certainly a defining one nonetheless.

2. Chris Jericho Debuts (finally)

August 9, 1999

I’m an admitted Chris Jericho slappy, but this truly was an unforgettable moment. After being the best thing on WCW Nitro on a consistent basis yet still being buried, fans were truly excited to see what Jericho would be able to do in the WWE. Based on the Y2J countdown clock that had been running on WWE programming for weeks before his debut, it was clear that Jericho was finally going to get the push he deserved. When he finally walked out on August 9, 1999, the crowd popped accordingly. That he was interrupting one of The Rock’s promos immediately established Jericho was a bona fide superstar. Even after getting verbally bested by The Rock, it was still clear that “Raw is Jericho.”

3. Nitro/Raw Simulcast

March 26, 2001

If the DX invasion of Nitro was insane, seing Nitro simulcast on the airwaves of WWE Raw was surreal. That’s exactly what happened, though, on the very last episode of WCW Monday Nitro. At that point, every wrestling fan knew that WWE was buying WCW, and it was referenced throughout that episode of Nitro. In the simulcast, Vince reveals that he has killed Nitro by buying WCW. Then, in the mother of all twists, Shane McMahon appears on-screen at Nitro in Panama City. He reveals that, “The deal with WCW has been finalized, and the name on the contract does say McMahon. However, the name reads SHANE MCMAHON!” Cue the stunned Vince face. Of course, this angle could have been truly revolutionary. In the end, though, for as great as it started, the “Invasion” angle would be one of the great disappointments of the modern era in professional wrestling.

4. Stone Cold and Mike Tyson

January 19, 1998

When it comes to bad ass sports figures in the 1990s, two names immediately come to mind: Mike Tyson and “Stone Cold” Steve Austin. In 1998, Mike Tyson, fresh off biting Holyfield’s ear and a prison sentence for rape, was probably the most terrifying and unhinged athlete in the world. Thus, Tyson made the perfect celebrity to pair with the WWE’s Attitude Era. In this storyline, Tyson had been present at the 1998 Royal Rumble as a guest and was teased to have a big announcement the next night on Raw. That next night, Tyson stood in the ring with Vince McMahon. As McMahon begins talking about Tyson’s role in the upcoming WrestleMania, Austin’s glass-shattering music hits, and “Stone Cold” walks to the ring. What follows is one of Austin’s greatest promos ever. Austin acknowledges that even though Tyson calls himself the “baddest man on the planet,” Tyson’s got his “beady little eyes locked on the eyes of the world’s Toughest Son of a Bitch!” After throwing up a little bit of sign language for Tyson (the double bird, btw), an epic shoving match begins and the crowd absolutely explodes. This is something that would never be on WWE television today but was absolutely awesome back in 1998.

5. Mick Foley Wins the WWE World Title

January 4, 1999

If you’re looking for a moment that truly signaled the death of WCW, it would have to be Mick Foley winning the WWE championship on Raw. That, in and of itself, wouldn’t have been that big of a deal and certainly wouldn’t have killed WCW. It was the context of the situation and WCW’s boneheaded decision-making that makes this one of the truly defining moments in Raw history. After being trounced by WCW in the ratings for years due to the NWO angle, WWE had finally made some headway. Raw had pulled ahead of Nitro at this point, but the war was still raging. At this point, Nitro was being broadcast live, while Raw was pre-taped days ahead of time. This allowed WCW to, in an effort to regain ratings control, give away finishes of the pre-taped matches on Raw. Ultimately, this backfired in the worst way possible on January 4, 1999.

On that night, The Rock was facing Mankind (Mick Foley) in a No Disqualification match for the WWE Championship. There were DX run-ins, Vince was at ringside, and all hell was breaking loose. As this was going on, WCW announcer Tony Schiavone (under orders from Eric Bischoff) told Nitro viewers, and I quote, “If you’re even thinking of changing the channel to our competition, fans, do not. We understand that Mick Foley, who wrestled here at one time as Cactus Jack, is gonna win their world title. Ugh. That’ll put butts in seats.” With those words, roughly 600,000 (!) viewers turned the channel to watch “Stone Cold” Steve Austin make his return, smoke The Rock in the head with a steel chair, and drag Foley’s carcass on top of The Rock for the 1-2-3. And if you’ve ever wanted to hear what it sounds like when every single person in a crowd loses their damn minds, watch and see what happens when Austin’s music hits during that match. Unbelievable reaction.

This was on the same night as the dreaded “Fingerpoke of Doom” match between Hollywood Hogan and Kevin Nash over on Nitro. That disaster, coupled with the Foley win, set the ball rolling on the death of WCW.


Brad LaFratte (@BradLaFratte)

1. Mrs. Foley’s Baby Boy Dream is Realized

January 4, 1999

Mick Foley winning his first WWE Championship encapsulates everything that makes a top Raw moment. High drama and unpredictability. Legendary characters at the height of their popularity. A loud and energetic crowd. A compelling story with a feel-good ending. And a turning point in history. The importance of this occasion cannot be overstated. As a 13-year-old kid growing up in central Iowa, I was entranced by the bright colors and larger than life characters popping off the TV screen. It was truly a feel good moment.

The match itself was an epic No Disqualification brawl. The gutsy Hardcore Legend Mick Foley (wrestling as Mankind) went toe-to-toe with the WWE Champion The Rock. In true Attitude Era fashion, chaos quickly ensued, as members of The Corporation and DX made their way to ringside. The Corporation tried to cost Foley the match, but DX jumped in with the save, and the two factions came to blows on the outside of the ring. Then in the midst of the melee, Stone Cold Steve Austin made his triumphant return, he cracked The Rock in the skull with a steel chair and dragged Foley’s limp body atop the Corporate Champ for the victory. The noise of the crowd was thunderous. It was the perfect fairytale ending for the ultimate underdog who was told he would never make it in the WWE. There have been tons of great Raw moments, many of which appear on this list, but this moment more than any other sums up why us wrestling fans love wrestling and why Monday Night Raw is the most successful prime time episodic primetime show in history.
2. This is Your Life
September 27, 1999

I don’t think anybody watching Raw in the Attitude Era can forget “This is Your Life” hosted by Mick Foley (as Mankind) as a tribute to The Rock. It was a nearly 30-segment promo, which is unheard of with no interruptions on live television. They were probably given some guidelines to it, but clearly they went off on their own and took it on a unique path.

Rock was greeted by people from his path, including an old football coach and a high school girlfriend with Rock firing off some memorable one-liners like “Poontang pie your ass outta here!”

The whole thing was done to try to have Foley suck up to The Rock because The Rock was cool and Foley was awkward. Even though Foley was being nice, The Rock was a jerk to him and the fans still loved him for it. This was my favorite line: “The Rock’s birthday is May 2nd, you stupid son of a bitch!”

3. Pipebomb

June, 27, 2011

CM Punk’s “Pipebomb” promo ended Raw in a unique way as he sat on the stage in a Stone Cold shirt. Punk was given the chance to speak his mind about how he hates the idea that John Cena is the best because Punk believed that he was the best in the world. Punk talked about Cena being better than him at kissing Vince McMahon’s ass, just like Hulk Hogan and Dwayne (The Rock). It was funny when Punk said he was breaking the fourth wall and waved to the camera.

The promo was about Punk believing in himself. Punk coined the phrase “I’m a Paul Heyman Guy” that night while mentioning Brock Lesnar left while Punk claimed he would leave with the WWE Championship. He said he was the best in the ring, on the microphone and even on commentary. Punk admitted that it made him sick that The Rock was main eventing WrestleMania the next year and that made it feel really real. When Punk mentioned New Japan Pro Wrestling and Ring of Honor, it was really unique. Punk even said hello to his friend Colt Cabana.

Punk trashed Vince McMahon, John Laurinaitis, Vince’s idiotic daughter Stephanie, and doofus son-in-law Triple H and shortly after that, Punk’s microphone turned off. It was the end of Raw for that night. I can remember jumping on Twitter and people were amazed by that promo. It’s been seven years. I’m still amazed by it.

A few weeks later, Punk had a five-star match where he beat Cena for the WWE Championship and left the company. That was only just an angle, though, because Punk signed a new deal. But Punk did legitimately quit in 2014 because of some of the same things he whined about in this promo.

4. DX Invades WCW

April 27, 1998

The great thing about DX invading WCW, at least in theory, was that WWE had the guts to even do something like that. Raw was in Hampton, Virginia, that night. Nitro was in Norfolk, so WWE decided to take advantage of it by having the DX group of Triple H, Billy Gunn, Road Dogg, X-Pac and Chyna head to Nitro to try to cause a distraction while rallying the fans there to support WWE instead of Nitro. It featured a tank and a bullhorn with Triple H talking about starting a war with WCW.

There was a memorable shot of the DX guys on the tank trying to get through some door, but the door closed as they got closer. What would have happened if they got through? Maybe some sort of altercation with some WCW talent. There are a lot of different stories from both sides when it comes to that. Then again, Road Dogg had brothers who worked there, so he probably would have enjoyed seeing them.

I think any WWE fan who saw that really believed in the company’s ability to do anything to entertain us.

5. Hospital Visit

October 5, 1998

This was a classic comedy segment. Vince was in the hospital after getting beat up by The Undertaker and Kane, so Mankind paid a visit. Vince was grumpy because he was hurt and in no mood for it, so Foley brought Yurple the Clown with him. That made Vince even more angry. Foley even had a sock puppet for Vince that he called Mr. Socko, which Vince hated even more.

Later in the hospital, Vince told a nurse he can’t wait to get out of there and she mentioned the doctor. It was Steve Austin dressed like a doctor and he destroyed Vince in the hospital room. Austin nailed Vince with a bedpan leading to the “Bedpan McMahon” name of this segment. It became another classic moment with Austin beating up Vince.


J.T. Nutt (@jtthenutt)

1. Daniel Bryan’s Retirement Speech

February 8, 2016

I cried. You’re damn right I cried. “Like a hungry angry baby” to steal a line from Serenity. Daniel Bryan got over the hard way. A huge “indy guy” that made it big. Did whatever he was asked and sometimes was able to make magic. Kane and Daniel Bryan looked horrendous at first, but they pulled it off and the Anger Management sessions became gold. Then Daniel had to beat the McMahons thanks to the “Yes!” movement. Years of wear and tear, and a bad bump in a match against Randy Orton (that Orton put a stop to) finally forced Daniel to retire. His speech was great. It was full of emotion and some laughs. I thought HBK had the best farewell speech but Daniel took his to another level. When wrestling and real life hit that magical blend, it’s deeply satisfying. (As long as it’s not the Pillman v Austin gun incident). When you are reminded that these superstars are human, it drives it home even more. Daniel never had “the look” but his persona, ability, and pure likeability as a human being got him over with the fans. Yes it’s fun to cheer for the underdog and that was one of the best underdog stories in pro wrestling history.
2.  The Pipe Bomb
 CM Punk got over faster than WWE pushing Braaaaaaaauuunnn. I remember Punk walking up to the ramp and sitting down. I didn’t know a ton about Punk other than you don’t spill his diet soda and he had slept with / dated pretty much every Diva at the time. To be honest, at that time, I was about ready to check out of the WWE. It had become stale, and I felt like I was watching out of duty, not because I liked the show. Then he dropped the pipe bomb and it was like “HOLY SHIT!” The shout out to Colt Cabana, the fact he dared to say “WRESTLER” and not “entertainer”.  It was so well executed. Punk was awesome and Cena always brings the best out of people.

3.  Nexus Debuts

June 7, 2010

How  do you get 8 guys over in one fell swoop? You have them surround the ring, beat down Cena, then destroy the ring and everything around it. It took me back to the days of the nWo where they would show up and destroy everything and leave. Daniel Bryan even got fired for this. They felt his choking out of Justin Roberts? with the cable was too far. But it was unexpected and well executed.  Something that the WWE struggles with but when they actually accomplish it, it’s awesome. It was also nice that they didn’t turn it into the nWo 2.0. Sucks that Wade Barrett got hurt because Nexus had a lot of potential. A lot more than the Corre ever did.

4. Y2J Debuts 

August 9, 1999

We had the clock countdown forever. Didn’t know what it was going to before, but boy was the payoff worth it (unlike the Anonymous Raw GM). Jericho was one of the better performers in WCW. He really carried the cruiser weights and was a dynamite heel. He interrupted the Rock and the crowd went insane. Much like the Miz now, he’s so good at being a heel, you love him, more than the faces. Jericho in the WWE helped the WWE more than it helped Jericho. He should go down as one of the best of all time and his debut was epic.

5. Sting is in the Ring at Raw

March 16, 2015


This happened in Des Moines and we were in the front row for it. Sting being involved with the WWE was something that was never going to happen, it was never supposed to happen, it was like the Cubs winning the World Series or Cleveland winning anything. There were things you never thought would happen. But Sting in a WWE ring? It happened. The Wells Fargo Arena went ballistic. Then Sting went ballistic.His run was cut short in the WWE. But he made his in ring debut in Des Moines, Iowa during an episode of Raw.


Agree with the guys? Disagree? Think that we missed something vital? Join the conversation in the comments or hit us up on Twitter.

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Jason Mitchell 65 Articles
Staff Writer

Jason grew up in Iowa but couldn't bring himself to like Iowa or Iowa State. Instead, he married a Cornhusker. Jason has taught junior high, high school, and college English but is now a stay-at-home dad to four kids. He also has an encyclopedic knowledge of reality shows and 1990s professional wrestling.

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