Monday Night Raw has been WWE’s flagship program since 1993 and is currently the longest running episodic television program in history, as WWE often likes to point out. Raw has come a long way since the first episode aired on January 11, 1993 and left us many indelible moments over the years.
From Stone Cold crashing The Corporations party with a beer bath to any one of Stephanie’s on-air weddings to Mick Foley winning his first WWE Championship, some of my fondest childhood memories are related to watching wrestling and especially Raw, since PPV’s weren’t broadcast on Indian television in those days.
Going through all the epic moments from Raw over the years, combing through them with a fine comb and selecting just the 10 best moments was one of the hardest things I’ve had to do in a long time. I looked at various factors while making my final list like the surprise factor and impact and most importantly, how memorable the moment was while looking back.
With that out of the way, here are the top 15 moments in the history of Monday Night Raw.
15: Pillman’s got a gun
Brian Pillman and Steve Austin were good friends since their days at WCW, but in 1996 they were in the middle of an intense blood feud in the WWF which led to one of the most memorable and controversial moments in the history of Monday Night Raw.
At the time, Pillman was at home recovering from a legitimate broken ankle so WWE sent over cameras to do an interview on Raw. Unbeknownst to everyone involved, Stone Cold Steve Austin had gotten wind of the cameras heading to Pillman’s house and decided to drop in unexpectedly himself.
Austin showed up and beat up a whole load of Pillman’s friends who’d tried to stop him. The segment had a level of realism that wasn’t common for television at the time and especially not professional wrestling programming. After taking care of Pillman’s friends Austin moved on to try and break into the house. At the same time, cameras inside the house showed Pillman brandishing a gun to protect himself and his wife.
When Austin finally broke in the screen went black as Pillman pointed the gun at Austin while screaming as Austin was being restrained by other WWE officials, with Kevin Kelly yelling “Call the police!” behind him and Pillman’s wife crying on the sofa.
The whole scene had an air of chaos and a shock factor which was unique to wrestling at the time and can be seen as an early precursor to the Attitude Era that started around a year and a half later. WWE created shockwaves with the segment with many parents groups complaining and many individual parents writing in saying that their kids would never watch WWE programming again.
However, ratings only went up after the segment.
14: Evolution forms
One of the iconic moments in the history of Monday Night Raw was the night of 20th January, 2003 when Evolution formed.
Triple H had just been taken to the brink by Scott Steiner at the Royal Rumble the night before, only escaping with his title with a little help from Ric Flair and a lot of luck. The night started with Triple H backing out of his rematch with Scott Steiner claiming he wasn’t medically cleared with Ric Flair nominating Batista, who had just been drafted from SmackDown, to face Steiner instead.
Batista and Steiner squared off in the ring later in the night with Flair at ringside. However, a young Randy Orton interfered during the match to attack Scott Steiner with Triple H joining in later too. The foursome gave Scott Steiner a fierce beating and one of the most popular factions in the modern era of the WWE was formed. Evolution had arrived.
13: Triple H takes over DX
30th March, 1998 was a very important date in Triple H’s career. Shawn Michaels had just lost to Stone Cold Steve Austin at Wrestlemania 15 before going on hiatus due to injury.
Triple H came out on Raw accompanied by Chyna and the fired up HHH called out Michaels for failing to win at ‘Mania and for failing DX. Triple H declared himself as the leader of a new DX army before introducing the new members. The first person out was X-Pac who was back in the WWE after a stint at WCW as Syxx.
This happened at the height of the Monday Night Wars between WWE and WCW and Vince let the returning X-Pac have a free go at the live mic with a chance to clear out all his grievances about WCW.X-Pac called out the Eric Bischoff, Hulk Hogan and others in WCW live on international television for the way he’d been treated in his last few days with that company.
He followed this by saying that Triple H had called him on the phone and asked for his help to reform a new version of DX, even going far as saying that Kevin Nash and Scott Hall would have joined them if they hadn’t been contractually obligated to WCW.
The question on everyone’s mind that night was whether Triple H would be able to carry DX without Shawn Michaels there. As wrestling history has taught us, the answer was a resounding yes.
12: Seth Rollins turns on The Shield
The Shield are the most dominant faction in the current era of the WWE. They ran roughshod through the entire WWE roster following their debut and plowed through both midcarders and veterans alike, remaining undefeated in six-man tags for almost six months following their debut. The trio worked like a well-oiled machine and they took on whatever opponent was put in front of them and eventually started feuding with Triple H who brought in Randy Orton and Batista to reform Evolution to take on The Shield.
The Shield vanquished Evolution in two pay-per-view matches including a six-man elimination tag team match at Payback 2014 in which The Shield won without any of its members eliminated. The night after, Triple H came out on Raw to address The Shield and told them that since he couldn’t defeat them, he had to activate plan B.
At this point, Seth Rollins took out his brothers from behind with a steel chair, to the audible gasp of the audience present. Rollins turned his back on Dean Ambrose and Roman Reigns to align with Triple H and The Authority, effectively ending The Shield.
Will The Shield reunite ever again against a common enemy? I sure hope so.
11:
Jeff Hardy fails to win the WWE Championship but wins The Undertaker’s respect
On the 24th June, 2002 episode of Raw, Jeff Hardy found himself in the unlikely position of challenging The Undertaker for the WWE Undisputed Championship in a ladder match. The Undertaker was in the middle of his ‘American badass’ character at the time and was playing the part of the big dog in the yard who was playing with his food i.e. Jeff Hardy.
When Jeff Hardy walked into the arena that night, neither The Undertaker nor the fans in attendance had expected Hardy to put on the fight he did. Jeff Hardy took The Undertaker to the brink and came within inches of grabbing the belt on quite a few occasions. An iconic moment of the match was when Jeff laid out Taker with a chair and while he was climbing the ladder J.R. on commentary screamed “Climb the ladder kid! Make yourself famous!”.
Jeff earned everyone’s respect that night even though he’d failed to win the title. After the match, even though he’d just lost and could barely stand, Jeff called out The Undertaker on the mic as he was walking away saying that Taker had failed to destroy him. Taker walked back into the ring and instead of pounding the helpless Hardy into the ground, Taker lifted his hand as a sign of respect.
10: Shane McMahon buys WCW/Raw and Nitro simulcast
March 26, 2001 was a historic date in the history of the WWE, professional wrestling and television itself. It was the date of the Raw and Nitro simulcast and the date of the final episode of WCW Monday Nitro. WWE had finalized their purchase of WCW earlier and Raw started off with the iconic moment with Vince looking at two separate television screens, one broadcasting Raw and one broadcasting Nitro with Vince announcing his purchase of WCW.
Vince came out later in the evening to cut a promo in the ring, that was shown on both Raw on TNN and Nitro on TNT which was a historic moment in television history. As Vince announced his purchase, Shane showed up on Nitro to tell Vince that even though a McMahon had purchased WWE, it wasn’t Vince, it was Shane.
The segment was historic, with North America having only one major wrestling promotion at the end of it, the last promotion standing was the WWE.
9: Vince McMahon is revealed to be the higher power
In the middle of 1999, The Undertaker began terrorizing Mr. McMahon and his family in a bid to take over the World Wrestling Federation. Before the beginning of this classic storyline, Mr. McMahon had been the biggest heel in the world of professional wrestling during his various feuds with Steve Austin. However, the storyline with the Undertaker and his Ministry of Darkness showed Vince in a completely different light as the sympathetic father and family man trying to protect his family and young daughter from evil.
During the Ministry of Darkness’ reign of terror, Undertaker had repeatedly pledged loyalty to a ‘higher power’. On the June 7, 1999 episode of Raw, Undertaker announced that the ‘higher power’ would finally reveal himself. To everyone’s surprise, in one of the most nonsensical storyline twists in WWE history, the ‘higher power’ was revealed as Mr. McMahon himself.
Even though Mr. McMahon being the ‘higher power’ ruined one of the best storylines in the Attitude Era, the moment where Mr. McMahon took off his hood and revealed himself with the iconic line “It was me, Austin, it was me all along” is one of the most memorable Raw moments.
8: Bret screwed Bret
Which pro wrestling fan doesn’t remember the Montreal Screwjob at Survivor Series 97? Bret Hart lost his title in front of a full house in Montreal after being screwed by Mr. McMahon for refusing to drop the WWE Championship to Shawn Michaels with his contract expiring within a week. With Bret about to sign for WCW, it’s easy to understand why Vince had to stoop to the level of actually screwing Bret Hart. If Bret had shown up on WCW with the WWE’s top title it might have led to WCW winning the Monday night war.
The following night, Vince sat down for his infamous interview with Jim Ross the following night on Raw explaining the reasoning behind his actions. He said that even though many would say that Vince screwed Bret, Vince had no option. Bret’s refusal to do the job in Montreal before his contract ended had forced Vince’s hand. Bret had screwed Bret.
Here’s what Vince had to say in the interview- "Some would say I screwed Bret Hart. Bret Hart would definitely tell you I screwed him. I look at it from a different standpoint. I look at it from the standpoint of: the referee did not screw Bret Hart, Shawn Michaels certainly did not screw Bret Hart, nor did Vince McMahon screw Bret Hart. I truly believe that Bret Hart screwed Bret Hart. And he can look in the mirror and know that."
7: Triple H turns on Shawn Michaels
In 2002, Shawn Michaels returned to the WWE following a 4-year absence due to a career-threatening back injury. On the July 22nd episode of Raw, a week after the breakup of the NWO, Triple H convince the returning Michaels to reform DX. The duo came out later in the night to their old music, doing the crotch chops that were so emblematic of DX.
They made their way down to the ring and did their iconic pose in the middle of the squared circle. Then, to the shock of everyone in attendance and everyone at home, Triple H pedigreed Shawn Michaels in the middle of the squared circle.
Triple H later said that the DX reunion had been a ploy to lure Shawn Michaels into the ring and he had been tired of being Michaels’ lackey the last time DX was around. This led to the epic No Holds Barred match between Michaels and Triple H at SummerSlam 2002.
6: The Pipebomb
The June 27, 2011 episode of Raw will always be remembered for one thing and one thing only, CM Punk’s pipebomb.
The main event of the night was a tables match between John Cena and R-Truth. Near the end of the match, as John Cena was about to give Truth an AA through the table, Punk ran down the ramp and knocked over the table. As Cena and Punk brawled, R-Truth took advantage and speared Cena through a table.
After the match, Punk grabbed a mic from ringside and walked back up the ramp where he sat down and delivered one of the best promos in the history of the WWE. His promo hit really close to home and highlighted many issues with the WWE that fans had been complaining about for a long time.
He began by addressing the fallen John Cena saying that he didn’t hate or like Cena, but he just hated the idea that John Cena always had to be the best and that Cena was as good as Hogan at “kissing a**”. His rant continued with shots fired at The Rock, Vince McMahon, his “Idiotic daughter” Stephanie and his “doofus son-in-law” Triple H while he also namedropped NJPW and Ring of Honor which was a strict no-no on WWE programming while also breaking Vince’s beloved fourth wall and giving a shout out to Colt Cabana.
Punk only stopped his rant when his mic was cut.
That day CM Punk became the voice of every WWE fan disgruntled by Vince McMahon’s decisions. Punk’s promo made mainstream news and his feud with Cena heading into Money In The Bank was one of the hottest of this decade. However, what we remember more than the match is the promo on Raw itself. The promo was just so real and uncharacteristic of WWE’s watered down PG Era programming that it left an indelible mark on the minds of fans.
5: Test and Stephanie’s wedding
Test and Stephanie’s wedding in on the 29th November, 1999 edition of Monday Night Raw is arguably the most memorable and jaw-dropping wrestling wedding of all time.
Vince McMahon’s innocent young daughter was all set to get married to her sweetheart at the time, Test, after Test had finally managed to convince Vince, and especially Shane, that he was fit to marry her even though he was a wrestler. The whole episode centered on the wedding with JR and Jerry Lawler starting the episode by welcoming fans to the wedding which was the final segment of the night. Interspersed through the matches all night were vignettes of Stephanie’s bachelorette party in Vegas,
Everything was going according to plan with the wedding, with Test and Stephanie in the ring with Vince and others, until Triple H’s music hit. Triple H came out to the ramp and said that he had a tape that everyone needed to see before the wedding could go through.
The video on the titantron showed Triple H in his car driving around in Vegas. He drove up to a drive-thru wedding chapel. As he drove into the “Little White Chapel” the camera panned to show a passed out Stephanie McMahon in the seat next to Triple H. He somehow managed to convince the lady who worked there to let him get married to an unconscious Stephanie McMahon.
The cameraman turned out to be the bartender from Stephanie’s bachelorette party who’d probably drugged her and as Triple H drove away, we saw that his car had a ‘Just Married’ sign behind it.
Everyone in the ring lost it, especially Test. Stephanie just cried and screamed “I hate you” at Triple H while Vince looked like he was on the verge of exploding. No one saw the twist at the end with Triple H interrupting the wedding, which makes this one of the best Raw moments of all time.
4: DX invades WCW
The late 1990’s in professional wrestling is known as being the most lucrative time in the business for everyone involved. Ratings were at an all-time high and WCW and WWE battled it out every Monday night to see who would come out on top. The rivalry was so heated that at one time, Eric Bischoff started giving away Raw results on WCW programming, with Raw being taped every other week and WCW live every week. Bischoff would berate Vince and the WWE week after week before WWE finally retaliated.
On April 27, 1998 WWE hit back when WCW and WWE were holding shows miles away from each other near Norfolk, Virginia. DX led by Triple H, put on camouflage, got into a jeep, and launched a full-scale assault on Monday Nitro, all of which was broadcast live on Monday Night Raw. It was an unforgettable moment in the history of professional wrestling with one of WWE’s top guys and his mates outside WCW’s venue with a loudspeaker.
WCW had no idea at how to deal with the DX Invasion and when DX tried to drive a truck into the stadium, WCW management decided to not let them enter the WCW venue which only made WCW look like a bunch of cowards. After spending years telling their fans that they wanted an all-out war with the WWE, WCW blinked, no matter what the reason was.
Road Dogg, Bad Ass Billy Gunn, X-Pac, Triple H, and Chyna spent the rest of the Raw in the streets with the fans getting them to swear alleigence to fans, some of whom even had WCW t-shirts on.
3: Stone Cold meets ‘Iron’ Mike Tyson
Mike Tyson was at the height of his fame in the late 90’s when WWE brought him in to be a guest enforcer at the Wrestlemania 14 match between Shawn Michaels and Stone Cold Steve Austin. Tyson was suspended at the time for biting off a part of Evander Holyfield’s ear during a match and people genuine thought Tyson was off his rocker.
On the January 19, 1998 edition of Raw, Mr. McMahon and Tyson were in the ring with Tyson’s entourage when Austin’s music hit. Austin interrupted to tell Tyson that he was sick of the attention he was getting and that Tyson was in Austin’s world now. Austin and Tyson squared off against each other as Vince’s face turned red at Austin interrupting such a significant moment.
Things got heated between Tyson and Austin leading Tyson to shove Stone Cold while led to a melee with almost 30 people trying to keep the two of them apart. As Austin left the ring McMahon yelled at Austin saying that he had ruined everything.
The chaos of the scene epitomized Raw’s cutting edge programming in those days. These are the kinds of moments that are still fresh in our minds so many years later.
2: Stone Cold drives a beer truck into Monday Night Raw
The Raw before Wrestlemania provided us one of the most memorable and iconic moments in Raw history.
Mr. McMahon, Shane and the WWF Champion The Rock were in the ring talking trash about Stone Cold, who was set to challenge The Rock at Wrestlemania 15 for his championship. Then, Stone Cold’s music hit and the crowd erupted as Stone Cold drove a freaking beer truck into the area. He got onto the roof of the truck to cut a promo before taking out a hose and dousing Vince, Shane and Rock with beer.
What made this moment even more memorable was the way that the trio reacted to getting the beer bath, with Vince doing a swimming motion in the middle of the ring while The Rock repeatedly tried to stand while Stone Cold’s beer assault took him off his feet time after time.
Moments like these are what made Raw and the WWE so special to our generation of kids, something that the kids of the PG Era won’t experience in the same way.
1: Mick Foley wins the WWF Championship
This was the moment where the WWE finally managed to turn the tide in the Monday Night Wars. It was the night remembered for WCW commentator Tony Schiavone “butts in seats” comment caused millions of household change channels over from Nitro to Raw to see the beloved Mick Foley (wrestling under the Mankind persona) win his first WWF championship from The Rock.
Mick Foley and Rock took on one another in a blockbuster main event with The Corporation helping The Rock and DX on the side of Foley. With the odds against him, Foley finally won with the help of Stone Cold who intervened to take out The Rock with a Stone Cold Stunner after which Foley pinned Rock to achieve his childhood dreams. Fans in attendance lost their minds and some even wept as DX lifted the victorious Foley on their shoulders and paraded him around the ring. Mick Foley was finally WWE Champion.
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