WWE is celebrating Raw’s 25th anniversary tonight in a stacked show. A couple of Daily DDT’s writers share their favorite moments.
How crazy is it that Monday Night Raw has been on air for twenty five years!? It really does seem like the time just passes by in an instant when I think of Raw and everything that has transpired over WWE’s flagship show.
And in that span of 25 years, the show has damn near seen it all. There have been great moments, bad moments and some ugly moments in between. These are moments that defined careers, legacies and the tenure of what Raw is today. The Miz cashing in his Money in the Bank to win the WWE Championship would be one moment. Those such as Mick Foley benefitted tremendously thanks to Raw.
Controversy peeped in time and time again from Attitude Era moments to present time. There have been moments such as Jerry Lawler suffering a heart attack that fans were in fear of wondering if he would make it through the night. Who could forget Edge’s and Daniel Bryan’s emotional retirement speeches? There were tribute shows for talents like Owen Hart and Eddie Guerrero. There was a live sex celebration (that a lot of us would like to forget…), contests that were less than stellar for today’s WWE, a few “This is Your Life’s”. Raw has been the cornerstone of all of things entertainment.
Debuts have been instant moment makers for the flagship show. Many talents over the years have announced their arrival on Raw. Chris Jericho had one of the most impressive Raw debuts in history. In the last few years, the Raw after WrestleMania is one of the most anticipated Raws due to a possible debut from other stars, mainly from NXT. Those such as Paige, The Revival, and Enzo and Cass made their main roster debuts the night after WrestleMania.
Whether it was a match, backstage segment, or in-ring segment one thing is for sure that it all went hand in hand to make Raw’s legacy stand strong. While most of us long for the days where Raw was non-stop fun, there’s something to be said for a show to remain on the air this long. As I worked on this piece, I am reminded that Raw still is the place to be. Raw still has that “it” factor despite its former glory days. Many of us have said that if there is a better creative team in place, Raw can achieve that consistent fun factor again.
Raw 25 is tonight, and it is sure a night that we won’t forget anytime soon. There is a lot of promise to see even more great moments and perhaps once in a lifetime ones. The show is stacked from top to bottom. One has to wonder how everything will fit in on the show.
Photo courtesy of wwe.com
To get hyped up for the show, I decided to come up with a roundtable of sorts to talk about some of our favorite Raw moments. This isn’t your “Top moments in history” or a countdown. This is us recollecting our thoughts and memories of moments that stood out to us. We aren’t just writers, we are fans first.
I was in high school during the Attitude Era, and those years are filled with memories of hanging out with my brother and cousin watching Raw by ourselves while our parents went to dinner. Or in college during the Ruthless Aggression Era, my girlfriends and I would order pizza and buy junk food while watching Raw. Raw is huge part of my life as I’m sure it is for others too. Again, we all bitch and moan about what could be better, etc. but deep down we all want Raw to go on forever. Then, now, and forever, right?
Let’s stroll down memory lane and relive some great Raw moments, shall we?
Credit WWE.com
Mankind Wins His First WWE Championship: January 4, 1999
By Trace Johnson
The career of Mick Foley was growing faster each year heading into 1999, but nobody saw what was coming for the often-overlooked superstar. No matter which persona Foley was using, he always made things interesting and it always worked.
But heading into 1999, his Mankind persona was on a collision course with the top heel in the company, The Rock. After turning heel at Survivor Series 1998 and aligning himself with The Corporation, The Rock was the WWE Champion heading into a battle against Mankind for the championship on the January 4, 1999 edition of Raw.
With The Corporation and D-Generation X ringside, The Rock and Mankind would take part in a match and night that changed wrestling forever. The deck was stacked against Mankind from the start, but after DX thwarted off The Corporation, Stone Cold Steve Austin’s presence would be felt in what can be described as the loudest pop in WWE history.
Austin took out The Rock with a chair and put Mankind on top off The Corporate Champion to get the win amidst a frenzy in the crowd. Foley had won his first WWE Championship in unbelievable fashion, but the night would be slightly tainted due to WCW revealing the results of the title change. However, that move would cost WCW over half a million viewers and, in turn, the WWE’s arch rival lost the ratings that night.
Whoever laughs last laughs best, and the WWE was laughing best thanks to a monumental night for Foley and the company as a whole in their battle against WCW.
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CM Punk’s Pipe Bomb: June 27, 2011
By Trace Johnson
The summer of 2011 saw the emergence of an angle never before seen in the WWE thanks to the services of CM Punk. There was no denying Punk had star quality, but his star quality would reach a historic level following a promo that changed the WWE forever.
Punk had been successful in the WWE over the previous few years, but his success would reach another level in his feud with John Cena in the summer of 2011. Following a match featuring Cena, Punk went on a verbal tirade that is now known as the Pipe Bomb promo that blurred the lines between reality and storyline like no promo had done before.
The Straight Edge Superstar went off on Cena, the WWE as a whole, the McMahons, and everything else to the point where everyone watching believed it was a shoot promo instead of a scripted one. It even got to the point where Punk’s mic was cut off and there were actually reports that he had been fired following the promo as his contract was set to expire following the Money in the Bank pay-per-view.
It was arguably the most well-done, realistic promo in WWE history and helped launch the career of Punk. He went on to defeat Cena at Money in the Bank for the WWE Championship and appeared to have walked out with the title. Punk would go on to have a lot more success over the next couple years or so before his exit in early-2014.
No matter how his time ended in the WWE, Punk’s Pipe Bomb promo was a legendary moment in the annals of WWE history and will live on forever among the WWE universe.
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Stone Cold Douses The Corporation In Beer: March 22, 1999
By Trace Johnson
The year 1998 saw the emergence of the single biggest star in WWE history in Stone Cold Steve Austin. The Texas Rattlesnake’s momentum kept growing from there as 1999 began and Austin’s path would cross with The Rock at WrestleMania 15.
Austin had been butting heads with the McMahons for the better part of a year by the March 22, 1999 edition of Raw, but what he would do on this Raw is still considered arguably the best moment in the show’s now 25-year history. With Vince and Shane McMahon in the ring along with The Rock, Austin had a big surprise for The Corporation.
With The Corporate Champion cutting a promo, Austin’s music hit and out came The Texas Rattlesnake, in a beer truck. The truck went all the way down the ramp in front of the ring and Austin cut a brief, yet awesome, promo of his own. The live crowd popped as you might imagine, but nothing like what was next.
Stone Cold doused both McMahons and The Rock with beer and pure chaos took place. The sight was something to be seen and Vince selling the beer attack by swimming in the ring was pure brilliance. And at WrestleMania 15, Austin defeated The Rock for the WWE Championship and the two would go on to define the biggest era in WWE history.
Out of all of Austin’s antics, the beer truck is arguably the best of the bunch in a long line of unforgettable moments.
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The Bedpan Incident: October 5, 1998
By Trace Johnson
The Stone Cold Steve Austin vs. Vince McMahon feud throughout much of 1998 went on to be arguably the most important and profitable feud in WWE history. But on an early-October night, Austin took his hatred of The Chairman to another level.
Weeks of antics towards McMahon led Austin to another all-time great moment on the October 5, 1998 edition of Raw. McMahon was hospitalized after being attacked by The Undertaker and Kane and hilariousness would ensue. Mankind paid McMahon a visit to try and brighten his day, and thus Mr. Socko was born.
The chemistry between Mankind and McMahon in this segment was outstanding, but what was still to come was even better. McMahon was being checked on by a nurse before the “doctor” would give The Chairman a checkup he’ll never forget. Austin, dressed in doctor’s clothing, attacked McMahon in his hospital bed.
The attack would reach its peak when Austin took a bedpan and clocked McMahon over the head with it. Everything about this segment was perfect and this is quite possibly the funniest moment in the history of Raw. And the craziest part is this feud would still improve in the coming months.
Austin attacking McMahon in the hospital room with a bedpan perfectly sums up what made the Attitude Era great.
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D-Generation X Invades WCW Monday Nitro: April 27, 1998
By Trace Johnson
The Monday Night War between WWE and WCW in the late 1990’s was unlike anything the television or pro wrestling world has ever seen before. Raw and Nitro battled it out for ratings supremacy each and every week, but by the beginning of 1998, WCW had all the momentum.
Raw finally broke through with its first ratings win over Nitro in nearly two years on April 13, 1998, but just two weeks later, the WWE would fire and even bigger shot at WCW with the help of its rebellious group D-Generation X. What would ensue shocked everybody and showed just how serious the real-life rivalry was between WWE and WCW.
The April 27, 1998 edition of Raw saw several segments of DX invading WCW’s Nitro in Norfolk, Virginia when WWE’s Raw was in Hampton, Virginia. The members of DX drove a tank up to the building in which Nitro was taking place and got WCW fans to chant how much Eric Bischoff sucks and that they got their tickets to Nitro for free.
It was absolutely incredible, even more so when DX approached the gate to get in the arena before the gate was closed. In hindsight, WCW probably should have let DX in the building because it could have resulted in a huge ratings getter for Nitro. Regardless, it was an epic moment that truly signaled the war was on and that WWE was taking the reigns back atop the business.
The night in which DX invaded WCW Nitro was a historic night and it remains that some 20 years later.
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Eric Bischoff Named General Manager
July 15, 2002
By Sarah Hirsch
The 2000s was a huge decade for pro wrestling. WCW was long gone and WWF had transitioned into WWE. It was a major adjustment for fans that were used to seeing the best of both worlds so to speak. On top of all of that, WWE was split into two brands for the first time. With the shows on its own, there was a need for “authority figures” to run their respective shows.
Ric Flair was named “Co-Owner” of Raw, ending the Alliance storyline that took place over the summer. He would remain in that position until he lost a match against Mr. McMahon that was on the spot due to Austin’s infamous walk out. So with that left a void for someone to come take Flair’s place. This was in 2002, so the Ruthless Aggression Era was in its infancy while the company was still adjusting to major changes. But none of that compared to the man who would take Flair’s place on Raw.
This would start the general manager angles that are prevalent on both Raw and Smackdown today. McMahon would introduce former WCW foe, Eric Bischoff, to the WWE Universe as Raw’s new General Manager. The two embraced in a hug, which fans were floored at what just happened. There was no other way to describe this moment as “hell freezing over”. That was the first words I said to my best friends when I saw that on TV. What else could it have been? Considering the Monday Night Wars the two men waged against one another, it was such a surreal moment, almost like it was a dream. It was one of those moments that you thought you would never see in a million years.
Bischoff wasted no time in getting started. He would rule Raw for over three years before abusing his power got the best of him. McMahon ordered a trial before firing him in grand fashion, followed with Bischoff getting carted off by a garbage truck.
Because of Bischoff, there was the Elimination Chamber and Raw Roulette, with Elimination Chamber still around today. Who could forget his “nephew” Eugene? Bischoff on Raw was shocking but turned out pretty good for the Ruthless Aggression Era. He still remains one of the longest tenured General Managers in WWE history.
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Austin Confronts Iron Mike Tyson
January 19, 1998
By Sarah Hirsch
I cannot even begin to tell you what an amazing time it was to be a wrestling fan in the Attitude Era. The excitement and awe plagued the hallways at school often in regards to something happening in WWF or WCW. This moment for me was one of my top moments in Raw’s history. I was a freshman in high school and even though it has been twenty years (telling age here) since this moment, I remember the moment vividly and the reaction afterwards.
Mike Tyson was brought onto Raw in January of 1998 to hype up WrestleMania XIV. McMahon named Tyson as the Special Guest Referee in the WWF Championship match at WrestleMania XIV. As McMahon was conducting his interview with Tyson, Austin would make a thunderous appearance. What he did next would change WWE forever.
Confronting Tyson, Austin would belittle him before throwing his middle fingers in Tyson’s face. Tyson shoved Austin and a brawl ensued. Back then, the Internet was still growing and many fans didn’t even see the confrontation coming. The moment hit big overnight, making it on newspapers all over in addition to making broadcasts the next morning. It caught like wildfire and everyone was on board with Austin and Tyson.
Austin would win the Royal Rumble, earning his ticket to the main event of WrestleMania. At that time, Shawn Michaels was holding the WWF Championship as one of the ringleaders of Degeneration X. During the build, Tyson would join DX and assist them in attacking Austin. When WrestleMania arrived, Tyson would betray his allegiance to DX and assist Austin in his first WWF Championship victory. Afterwards, Tyson knocked Michaels out cold when he was confronted.
Perhaps this moment led to more celebrities appearing on Raw over the years. While some are rather forgetful, there were other moments that stood out in Raw’s 25 year history including Michael Straham, Jon Stewart and Hugh Jackman. But no other moment comes close to this outstanding confrontation that would shock the world.
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Divas Revolution
July 13, 2015
By Sarah Hirsch
The evolution of women in wrestling was a great slow burn that continues to build flames by the day. Up until the “revolution”, NXT was gaining momentum thanks to their Four Horsewomen in Sasha Banks, Charlotte Flair, Bayley, and Becky Lynch. They were breaking barriers and making waves in NXT while those such as AJ Lee and Paige were fighting to bring that same kind of recognition to the main roster.
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Lee shook the division to its core with her infamous “Pipebombshell” in 2013 that targeted the cast of Total Divas. She and Paige would battle throughout 2014 before Lee would be dethroned by Nikki Bella to much disappointment. One has to think that this went hand in hand with the emergence of talent in NXT and the need for refreshment in the Divas Division. Unfortunately, Lee would retire after WrestleMania 31, three months before the fruits of her labor would be realized.
Bella was still the Divas Champion at the time, on course to being its longest-reigning Champion. The controversial reign would take a detour in the summer of 2015. She was set to make a statement of the Divas Division when Paige would interrupt her, followed with Stephanie McMahon. From there, McMahon would declare that it’s time for a revolution before introducing Lynch, Flair and then Banks.
Photo courtesy of Sarah Hirsch.
I was in attendance at that Raw, and that moment live was amazing. As an avid follower of the Women’s Division, it was rewarding to watch those debuts and see the Division change before my eyes. Philips Arena was rocking that night with a hot crowd and a great show to boot. It was the best show I attended because of that moment, and made the overpriced ticket bought on StubHub (I was in 3rd row) worth the cost.
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Trish Stratus vs. Lita Main Event for Women’s Championship
December 6th, 2004
By Sarah Hirsch
It is no doubt that Trish Stratus and Lita account for one of the greatest women’s rivalries in WWE history. Stratus and Lita had rivaled on and off until this point being best friends in between. After being brokenhearted by Chris Jericho and Christian, Stratus and Lita would team up against both men at Armageddon 2003 in a Battle of the Sexes match. They would lose in their efforts, though it was a start of something much bigger.
Stratus turned heel at WrestleMania XX, Chris Jericho a loss against Christian and revealing that they were having an affair. In true Trish fashion, she proved that she isn’t to be underestimated no matter the role she played. As for Lita, she would get “kidnapped” by Kane earlier that summer that would result in a storyline pregnancy (‘it’s not my fault!’). Stratus had taunted Lita from time to time, which lead to the two battling it out at Survivor Series. Lita earned a disqualification, thus resulting in Stratus wearing a nose guard and the two having a rematch on Raw.
Prior to the match, Stratus would call Lita a “walking kiss of death” given the tumultuous year she had. Lita responded by kissing Stratus, which much to her disbelief would work in Lita’s favor by the time the match was over. Both women delivered in a stellar main event that saw Lita nearly breaking herself in half with a suicide dive to the outside of the ring on Stratus. Lita would win the Championship for the second time that night in her home state of North Carolina.
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It would be almost twelve years later for another women’s main event to happen on WWE Raw. Sasha Banks and Charlotte Flair would continue to make their rivalry historic by following in Stratus and Lita’s footsteps with a great match of their own. The match saw Banks capture the Raw Women’s Championship for a third time via submission in the stands, as it was a Falls Count Anywhere match. With the success of women today, there has been more main events featuring the women of WWE with Banks and Flair headlining Hell in a Cell in 2016.
Stratus and Lita’s feud will stand the test of time and set the bar for those women today. The company has some of the best talent today who can carry on the great legacy of women’s wrestling and that when done right, they are more than capable of carrying the main event.
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John Cena is Drafted to Raw
June 6, 2005
By Sarah Hirsch
John Cena was the hottest WWE Superstar walking in 2005. He had just won his first WWE Championship at WrestleMania 21 and his rise to Superstardom was still en route. Until then he was exclusive to the Smackdown brand and had never made an appearance on WWE’s flagship program. That would change in 2005 and so would his legacy.
For those of you who don’t know, the struggle was too real back then. Smackdown wasn’t easily accessible at the time. It would go from UPN to CW over the years, which then those channels were hard to come by. I had DirectTV and still couldn’t get those channels! There was no YouTube and no social media to see Smackdown unless someone you knew had the channels and taped it. My best friend would tape Smackdown and then we would all get together to watch it. She was our YouTube to watch Cena, Edge and the Undertaker just to name a few.
It was a matter of time before WWE’s hot property would make his presence felt on Raw. And yes, this was when EVERYBODY loved Cena. So when the draft came around, fans waited anxiously to find out who the first draft pick was. Chris Jericho would open the show with the Highlight Reel to interview the draft pick.
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The reaction was deafening upon Cena’s music playing. It cemented Cena’s importance as a WWE Superstar and the years to follow. It was his first Raw moment, but certainly not his last. Cena has been a part of some major Raw moments, mainly with CM Punk’s PipeBomb and the Nexus destroying him and the Raw set in 2010. How about Bray Wyatt’s children’s choir spooking him singing “He’s Got the Whole World in His Hands”?
Next: WWE: Peter Rosenberg and the Difference Between Character and Personality
To this day, Cena continues to make an impact on Raw despite his part-time schedule. He will make his first WWE appearance in 2018 on the 25th anniversary show. Rumor has it that we could see his next feud start there. We shall see.

