source: Barclays Center
Throughout 25 years of historic storytelling, WWE Monday Night Raw has captivated millions of wrestling fans. With next week being the celebration of Raw’s 25th year on air, I felt it was only right to recall my personal favorite moments in Raw history.
25. Pillman’s Got a Gun!
On the cusp of the Attitude Era, WWE was eager to push the envelope as often as they could, and they sometimes went a little too far. When Steve Austin and Brian Pillman were in WCW, they were known as a tag team called the Hollywood Blondes. Austin left for WWE, where he established his own “Stone Cold” character, and when Pillman came to WWE shortly after, they entered into a brutal feud.
After feuding for weeks, Brian Pillman conducted an interview at his home while he recovered from a broken ankle. Austin showed up at his house and Pillman pulled a gun on him. The scene erupted into chaos and the camera feed cut out. It came back and Austin had to be pulled away from the house, but Pillman kept the gun in his hand and didn’t show any fear.
Shocking events like these were only beginning in the Attitude Era, but this one did get a little out of hand. Pillman and WWE later apologized for the sensitive angle.
24. The Higher Power is Revealed
When Shane McMahon’s Corporation joined the Undertaker’s Ministry of Darkness, they sought out to face their common enemies—Stone Cold Steve Austin, The Rock, and Mr. McMahon. The merged group praised a “higher power” that brought them together.
Shane demanded that the leader of the Higher Power remove his black hood and reveal himself to Austin. The hood came off and Vince McMahon revealed himself. McMahon said that there’s nothing he wouldn’t do to make Austin’s life a living hell. Angry that Vince was behind everything (including the kidnapping of Stephanie), Linda and Stephanie came out and revealed that they had given their ownership of the company to Stone Cold Steve Austin. This moment was a huge swerve and left fans in shock.
23. Randy Orton Gets A Thumbs Down
Following a successful title defense against Chris Benoit, Randy Orton was hoisted onto Batista’s shoulders as the members of Evolution—Batista, Triple H, and Ric Flair—celebrated his victory. However, the celebration was short-lived: when Triple H gave Orton a thumbs up, he turned it to a thumbs down, prompting Batista to drop Orton on his back.
The entire group beat up Orton, bloodied his face, and embarrassed him, and then Triple H held up his World Heavyweight Championship. Triple H admitted his jealousy of Orton having the title, launching Orton into a feud with his former allies.
Evolution made Orton a household name just a year after his debut, and when he split from the group, he was put into a storyline with Triple H, one of the top guys in the company. This turn was completely unexpected and helped Orton become one of the main eventers in WWE.
22. Festival of Friendship
It is likely that Chris Jericho did some of his best work just last year. In 2017, he hilariously created the “List of Jericho” and coined “drink it in, man”, as well as worked alongside his best friend, Kevin Owens, who seemed significantly less excited about their relationship, but used it to his advantage.
The Festival of Friendship was built up for weeks, as Jericho wanted to celebrate his friendship with Owens and show him how much he meant to him. Jericho gave him a strange minimalist sculpture, a painting of the two, “Friendship the Magician”, and even brought out Gillberg just for Kevin Owens. In return, Owens gave Jericho a brand new list—with his name on it. He attacked Jericho and destroyed the Festival of Friendship set.
This segment just further proved how brutal Owens can be and helped establish him as one of the greatest heels in wrestling. The Festival was perfectly executed, from Jericho’s enthusiasm to Kevin’s lack of enthusiasm and his brutal beat down.
21. Dolph Ziggler Cashes In
As soon as his music hit, the crowd went wild. Dolph Ziggler took his Money in the Bank briefcase as the prime opportunity to challenge a hurting Alberto Del Rio for the World Heavyweight Championship. This match was full of intensity and unpredictability—people loved it so much that WWE had no choice but to turn heel Ziggler into a babyface.
He received one of the biggest ovations in WWE history. WWE fans can always recall those special moments when a wrestler becomes a star, and this was Ziggler’s moment. This moment has defined him as a superstar and can be considered the greatest cash-in in Money in the Bank history.
20. Daniel Bryan Retires
In one of the saddest, most unexpected retirements in WWE, fans were extremely saddened to watch Daniel Bryan’s career come to an end. In a tear-jerking segment in Bryan’s home state of Washington, he tells the crowd that he’s been wrestling since he was 18 and that within 5 months of his career, he had already had 3 concussions. Over 16 years, he had suffered too many concussions and he was unable to wrestle anymore.
He says that he’s so grateful to wrestling for making him happy for 16 years and for meeting his wife. He receives arguably the loudest “Yes” chant ever, and Brie comes out to the ring to celebrate with him.
Bryan’s passion for wrestling was contagious and is the main reason why it was so hard for everyone to see him walk away. Even with his work now as Smackdown general manager, his passion for the sport shines through.
19. Shawn Michaels Loses His Smile
Looking back, this may be one of the most ridiculous promos in WWF history. Due to an alleged knee injury, Shawn Michaels is forced to vacate the WWF Championship. However, Michaels comes off as pathetic. He said he felt like he couldn’t say no, so he took on a harder work schedule. He says he’s gonna go home and “see what’s left for him”. He had lost a few lot of things over the last several months, including his smile. “I don’t care if people wanna make fun of me because I’m an emotional guy.”
The interview was so weird and sparked even more controversy because it was believed that Shawn was vacating the title because he refused to lose to Bret Hart at Wrestlemania 13. Hart even stated that he thought Michaels was faking the injury to get out of the match, intensifying their feud even more.
18. Vince’s Limo Explodes
In one of the most insane moments in Raw history, Vince McMahon entered a limo at the end of the show and as soon as he shut the door, the limo exploded. Many fans were left in awe and shock, as WWE reported that McMahon was presumed dead, sending out a press release within a few hours. The incident was so realistic that even Donald Trump, who had worked in a storyline with McMahon at Wrestlemania two months before, called to see if Vince was actually dead.
Nobody expected “Mr. McMahon Appreciation Night” to end in his death. Unfortunately, the storyline was cut short and Vince had to appear two weeks later to address the real death of Chris Benoit. It was then reported that Vince faked his death to see what people really thought.
17. The Ultimate Warrior’s Final Appearance
Two days after entering the WWE Hall of Fame and less than 24 hours before his unexpected death, the Ultimate Warrior comes out to the ring and gives a bone-chilling speech. “Every man’s heart one day beats his final beat and his lungs breathe their final breath. And if that man did in his life makes the blood pulse through the bodies of others, it makes them believe deeper in something larger than life, then his essence, his spirit, will be immortalized.”
Warrior speaks about his legacy and about how the fans made him a legend and even talks about his heart beating its final beat and his spirit living forever less than a day before he passes away. As one of the most legendary superstars in WWE history, fans will never forget his final appearance before his untimely passing.
16. Sasha and Charlotte Main Event
For the first time in twelve years, a women’s match would main event Raw. Two of the top women’s wrestlers in WWE history went face-to-face once again on October 3, 2016 as Charlotte defended her Women’s Championship against Sasha Banks.
These two put on one hell of a match that left fans in awe of their athletic prowess, from suicide dives to hurricanranas to top rope moves to a brutal corkscrew moonsault on the outside of the ring. Sasha won her second Women’s Championship in this match, leading to a rematch that would co-main event Hell In A Cell in the first ever women’s Hell In A Cell match. This match was one of the landmark moments in the Women’s Evolution.
15. DX Invades WCW
This moment is that really sparked the Monday Night Wars, as WWE and WCW competed every Monday for better TV ratings. When Raw and Nitro were in the same state on April 27, 1998, DX decided to take a military Jeep to the arena that WCW was taping Nitro.
DX rode around the arena in the Jeep with a megaphone, shouting outside the building about how WCW sucks and Eric Bischoff sucks. They made lewd jokes as only DX can, and even tried to drive the Jeep into the arena, but the gates were shut and they weren’t allowed in. Although these sorts of antics were’t surprising, it was cool to see WWF superstars come close to an actual war with WCW.
14. WWE Draft
The draft marks a crucial turning point in WWE history. The first ever brand extension moved WWE into uncharted territory—they’d never done something like this before, but the risk was successful, as they would be able to showcase more superstars across two shows instead of having the same few main event stars on just one show. With the acquisition of WCW and ECW, WWE received an influx of superstars to fill both shows, and to switch up storylines, they would hold a draft yearly (except 2003 and 2005) until 2011.
The brand split sparked interbrand competition and allowed for more pay per views to be made, each one specific to either Raw or Smackdown. The split also separated some of the championships and made them exclusive to one brand. This moment on Raw was huge for the entire company as it would change the company forever.
13. Shane McMahon Returns
No one was expecting Shane McMahon to return when Vince presented his daughter with the Vincent James McMahon Legacy of Excellence Award. As she was accepting the award, his music hit and the crowd went nuts—this was one of the biggest surprise returns in WWE history.
Shane told Stephanie that she and Triple H were running the company into the ground: stock and ratings were low and there was a plethora of superstar injuries. He also revealed that Vince owed him for a mistake that he made years ago, and Stephanie was only in control because Shane let her be in control. Shane ordered to be in control of Raw, and Vince agreed, under one condition—he must beat the Undertaker in Hell in a Cell at Wrestlemania.
If Shane hadn’t returned last year, it’s possible that Smackdown wouldn’t even be competing with Raw, let alone thriving. Not only was his return a crazy shock, but it also gave us a Wrestlemania moment (see Shane jumping off the cell onto the announce table), as well as a successful Smackdown brand.
12. Nexus Takes Over
The introduction of the Nexus faction was like something we have never seen before. About 10 minutes into the John Cena’s match with CM Punk in the main event, Wade Barrett walks out to the ring. He gets to ringside and all of the members of the first class of NXT (back when it was a competition show) emerged from the crowd.
The group of eight ransacked the arena, sparing no one. They tortured John Cena, CM Punk and the Straight Edge Society, and even Jerry Lawler, Matt Striker, Michael Cole, and Justin Roberts (Daniel Bryan choked the man with his own tie, causing his release). Nexus tore the ring apart, ripping out the middle rope, peeling back the canvas, destroying the barricades, throwing chairs, and flipping the announce table.
While the Nexus seemed to fizzle out a bit eventually, their initial impact was definitely felt by WWE and the fans. People would remember this moment for years to come, and it can be argued as one of the most effective debuts for a group (or any superstar) in history.
11. Chris Jericho Debuts
In anticipation of the new millennium, Chris Jericho makes his awaited WWF debut, vowing to “save” the fans. He talks about how WWF is a “boring snoozefest that is in dire need of a knight in shining armor” and that no one cares about any of the superstars.
He cuts a fantastic promo for his debut, but then gets verbally destroyed by the Rock. As Jericho is being put in his place by the Rock, he gets more and more visibly angry. However, this was peak Dwayne Johnson, so even while he was burying Jericho, he made him look good. Jericho’s debut is arguably one of the most memorable in WWF/WWE history.
10. Mike Tyson Comes Face to Face with Stone Cold Steve Austin
When the WCW vs. WWE ratings war was fully underway was when Raw was at its most unpredictable and exciting. Mike Tyson was appearing on Raw just six months after one of the most controversial moments in sports history—when Tyson bit off part of Evander Holyfield’s ear. The Baddest Man on the Planet announced that he would make an appearance at Wrestlemania XIV.
Austin came out to the ring and calls out Tyson. He says he could beat Iron Mike any day of the week and flipped him off, causing Tyson to shove him. Tyson then became the “special enforcer” (whatever that means) for Austin’s match against Shawn Michaels at Wrestlemania XIV.
When Austin showed no fear in the face of Mike Tyson, he proved that he is the toughest SOB in wrestling. This moment is one of the best in all of the Attitude Era, helping to shape Steve Austin’s career at the top of the company.
9. Daniel Bryan Occupies Raw
This segment might as well have redefined Daniel Bryan’s career. Bryan led the “Yes Movement” to occupy Raw until he got a match with Triple H at Wrestlemania. Daniel Bryan’s supporters and members of the “Yes Movement” got into the ring and they chanted in and around the ring until Triple H and Stephanie came out.
The Authority tries to put a stop to it, but Bryan and the fans won’t budge. Triple H is forced to give in and the match is created. Bryan also bargains for himself to be entered into the triple threat match for the WWE World Heavyweight Championship if he beats Triple H.
This moment cemented Daniel Bryan as a WWE Legend. Throughout his WWE career, Bryan campaigned for the people in power to listen to the fans. He was the underdog and everyone was rooting for him. His resistance and determination made him the most popular in the company in the eye of the fans, but he continuously had to prove himself to the Authority. This segment proved that Daniel Bryan is one of the most popular and influential stars in WWE history.
8. Shane Buys WCW
Vince comes out to the ring and condemns WCW, saying that it is “buried” and is going nowhere, just like anyone who gets in his way, including his son Shane. Shane’s music hits and he doesn’t come out to the WWF ring in Cleveland. Instead, he comes out to a WCW ring in Panama City, Florida.
Vince is shocked to see him, but even more shocked when Shane reveals that he purchased WCW (cue exaggerated Vince gulp). Shane teams up with Stephanie, who owns WCW, to take on their father.
This battle, dubbed the Invasion, would’ve shaped up to be one of the greatest storylines of all time (if they didn’t mess it up). However, this moment marked the transition of WCW into WWE as WWE had officially purchased WCW.
7. Paige’s Debut
In a surprise debut at the Raw after Wrestlemania, Paige comes out to the ring to congratulate AJ Lee on her Wrestlemania victory. AJ slaps her and prompts Paige for her first match, putting her title on the line. Paige pulled off the upset and won the title on her first night on the main roster.
AJ’s title reign was built on the concept that she wasn’t like all the other divas, that she didn’t care about being on a reality show and that she was the only real woman who deserved the title. Paige proved that not only can she hang with the main roster women, but that women’s wrestling was becoming more and more prominent.
This moment is very important, both for NXT and for women’s wrestling. Paige was the one of the first female NXT call-ups and one of the first NXT call-ups since NXT was branded WWE’s developmental territory.
6. Ric Flair Retires
After over 35 years in the wrestling business, Ric Flair’s career came to an end at Wrestlemania 24. It would’ve been a bit sweeter if Flair actually meant it when he said he would never wrestle again (he wrestled in ROH and TNA for a few years after that), the nearly 20-minute segment was an amazing tribute to Flair’s legendary career.
With appearances from the Four Horsemen, Shawn Michaels, Ricky Steamboat, and even his entire family, this retirement was one of the most memorable in history. Raw closed with the entire roster emptying out onto the stage and at ringside to pay tribute to the wrestling legend.
5. Bret Screwed Bret
Just a week before at Survivor Series, Bret Hart had lost his WWF Championship to Shawn Michaels via a Sharpshooter he didn’t submit to. Vince McMahon conducted an interview with Jim Ross on why he told the referee to make that call.
In the segment, he admits that he will always own up to his actions and believes he makes more good decisions than bad, but insists that “Bret screwed Bret”. He says that Bret was disrespectful to fellow members of the company on his way out of WWE and if he was respectful like he should’ve been. He did it to himself.
This response to one of the most controversial moments in WWE history is what began to cement Vince McMahon as one of the greatest heels in wrestling.
4. Women’s Royal Rumble Announcement
Just last month, a huge step for women’s wrestling took place. It’s been a long time coming, but the women of WWE finally got a Royal Rumble match of their own. As Stephanie spoke to the Raw women’s roster, she recalled the key events in women’s wrestling in the past few years: first Hell in a Cell match, first Money in the Bank match, first women’s match in the Middle East. McMahon recognized how inspiring all of the women are, and vowed that they make history once again.
Every time I watch this announcement, I get goosebumps and tears in my eyes (and I’ve watched it plenty of times). This moment is another huge step for women’s equality in wrestling.
3. Rock, This is Your Life
After attacking the Rock the night before at Unforgiven, Mankind feels guilty and wants to make it up to him. He brought out Rock’s sixth grade home economics teacher, high school football coach, and high school sweetheart. Rock, however, was not having it. He had a problem with every one of these people, and in a last ditch effort, Mankind told Rock to open up his presents. He had been gifted a Rock’N’Sock Connection jacket and a Mr. Socko with his name on it, aptly named “Mr. Rocko”.
Foley then introduced Yurple the Clown and as a birthday cake rolled down to the ring, Mankind started singing happy birthday. The Rock stated that it wasn’t even his birthday, and then was interrupted by Triple H coming out to the ring with a sledgehammer in attempt to attack Rock, his opponent later that night.
This was the highest rated segment in Raw history. Rock was able to deliver greatness on the microphone (not unusual) and hit every catchphrase, and when you combine that with Mankind’s anxious excitement over all of these things he had prepared for this presentation, you get 20 minutes of greatness. This segment can be imitated (see Alexa Bliss and Bayley), but never duplicated.
2. CM Punk’s Pipe Bomb
During John Cena’s tables match with R-Truth, CM Punk interferes and causes R-Truth to send Cena through a table. What came next was one of the most jaw-dropping moments in WWE history.
The “Pipe Bomb” promo established CM Punk as one of the best guys in WWE history. He finally said what everyone in the locker room was too afraid to say, and his built up anger and frustration may have even taken it a bit too far. Watching this again made me wonder how he even was able to speak after calling out The Rock, Hulk Hogan, John Lauranitis, and Brock Lesnar by name. He mentioned that he may take the WWE Championship to New Japan or back to Ring of Honor, then gave a shoutout to his friend Colt Cabana.
They finally cut him off as he was telling a personal story about Vince McMahon. “You know the whole bullying campaign—“ His microphone was cut out at this moment, and you can just feel Punk’s intensity through your TV screen.
It’s no wonder we heard weekly “CM Punk” chants for years after he left the WWE. It’s toned down a bit, but fans may never stop clamoring for his return until it actually happens.
1. Rollins Betrays the Shield
The Shield was at the hottest point in their career—they had just defeated Evolution in a no Holds Barred elimination match and caused Batista two quit the WWE (for a second time). However, Dean Ambrose and Roman Reigns had no idea about Triple H’s plan B. Out of nowhere, Seth Rollins slams a chair into the back of Reigns. In shock, Ambrose just stares at his teammate before Rollins attacks him with a chair too. The arena is flooded with “you sold out” chants.
This moment was huge for all three Shield members, as it would skyrocket their careers. Fans were stunned and Rollins became one of the most hated guys on the roster, while fans sympathized with the Lunatic Fringe and the Big Dog (before they started to hate Roman).
Fans will always remember where they were at this moment and how shocking it was, and if it weren’t for Rollins’ betrayal, none of these three men would be at the star status that they all are today.
(below is a YouTube playlist of these top 25 moments)
https://www.youtube.com/playlist?list=PLqPcU6imlj9hpYWTZcwF7rNsL6dC0Q7F_
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