In honor of the 25th anniversary of Monday Night Raw, The Wrestling Estate is counting down the 25 greatest moments in the history of WWE’s flagship show.
25. Batista’s Thumbs Down, February 21, 2005
After winning the Royal Rumble, Batista had a life-changing decision to make: face JBL and John Cena for Smackdown’s richest prize or break up Evolution and challenge its leader, Triple H. The Animal’s actions spoke louder than any words, catapulting him into superstardom.
24. Milan Miracle, April 16, 2007
Mr. McMahon invited anybody out of the Milan, Italy crowd to challenge Umaga for the Intercontinental Championship. In one of the most exciting debuts in WWE history, Santino Marella answered the challenge and became the unlikeliest titleholder ever.
23. Vader Time, January 22, 1996
One night after debuting at the Royal Rumble, Vader squashed Savio Vega, dropping multiple Vader Bombs after the match. Officials tried to intervene, but the Mastodon simply swatted them away. WWE President Gorilla Monsoon then entered the ring to restore order, a grave mistake for the grandfatherly figure.
22. Here To Show The World, April 8, 2013
In one fleeting moment, Dolph Ziggler was on top of the world. Twenty-four hours after WrestleMania 29, he cashed in his Money in the Bank contract and won the World Heavyweight Championship from Alberto Del Rio. Just listen to that pop and wonder how it all went wrong.
21. Da Man Arrives, March 31, 2003
WCW’s only homegrown star finally landed on McMahon soil. Just like Chris Jericho did four years earlier, Goldberg made his presence felt by interrupting The Great One.
20. One Last Strut, March 31, 2008
At the time, Ric Flair had the greatest sendoff of any pro wrestler ever, surrounded by the loving embrace of his peers, proteges and fans. Unfortunately, the Nature Boy just couldn’t leave the memories alone.
19. This Is Your Life, September 27, 1999
Sometimes imitated, never duplicated (poor Alexa and Bayley), Mankind’s tribute to The Rock remains one of the highest-rated segments in Raw history. It was wacky, raunchy and instantly quotable, hilariously illustrating the love-hate relationship of the Rock n Sock Connection.
18. Zamboni 3:16, September 28, 1998
After McMahon’s master plan to screw Steve Austin out of the WWE Championship came to fruition, the boss held a ceremony filled with police and officials to crown either Kane or Undertaker with the title. Of course, a barricade has never stopped the Texas Rattlesnake from crashing the party. “I ain’t through with ya, Vince. I ain’t through with ya by a longshot.”
17. Festival of Friendship, February 13, 2017
All good things must come to an end – Chris Jericho found that out the hard way. Y2J celebrated his relationship with Kevin Owens in over-the-top, glitz and glamourous Las Vegas fashion. With his ridiculous bedazzled outfit, hilarious dancing and absurd gifts (plus Gillberg and Friendship the Magician), Jericho annihilated the friendship bracelet market and demonstrated why he’s the most sincere, thoughtful and generous man alive.
Unfortunately, Owens is the antithesis.
16. Icon vs. Icon, February 18, 2002
As Hulk Hogan proclaimed himself the biggest star in wrestling history, The Rock interrupted and challenged the Immortal One to a dream match at WrestleMania. Time stood still as the goatee and the eyebrow soaked in the dueling chants. The moment is even cooler in retrospect as Rock has surpassed Hogan in terms of mainstream appeal.
15. The Beast Returns, April 2, 2012
“Holy Shit” chants echoed throughout the American Airlines Arena as Brock Lesnar returned to WWE after eight years away. The Beast wasted little time in targeting his prey, delivering a thunderous F-5 to John Cena.
14. Milk-O-Mania, August 20, 2001
What better way to celebrate Austin Appreciation Night than putting a new spin on Austin’s classic beer truck moment? This gave way to my favorite J.R. line: “The Billion Dollar Princess has become the Dairy Queen!”
13. The Pipebomb, June 27, 2011
Not since Austin 3:16 and Bash at the Beach 96 has a promo shook the wrestling world. CM Punk broke the fourth wall, tearing into sacred cows like the McMahon family and The Rock, venting universal frustrations felt within the WWE Universe.
12. McMahon’s First Stunner, September 27, 1997
They say you always remember your first. Well, nobody has forgotten the first time that Vince McMahon ate a Stone Cold stunner, in the middle of WWE’s Mecca, Madison Square Garden.
11. Forbidden Love, November 29, 1999
It was supposed to be the happiest day of Test and Stephanie McMahon’s lives. Unfortunately, Triple H had already struck, revealing that the Billion Dollar Princess had a new last name.
10. The Upset, May 17, 1993
Raw’s unpredictable atmosphere was established early on as a regular squash match turned into the biggest upset of all time.
9. Nexus Invades, June 7, 2010
Nobody saw it coming. As Cena faced Punk in the main event, NXT Season 1 winner Wade Barrett sauntered down the ramp. Suddenly, his fellow participants emerged at ringside, attacking everyone and everything in their path. It’s been edited out of the WWE Network, but Daniel Bryan choked out ring announcer Justin Roberts, prompting his two-month dismissal afterward.
8. Beer Truck, March 22, 1999
On the road to WrestleMania, Stone Cold stopped by Albany, New York with a Coors Light truck, hosing down The Rock and the McMahons in hilarious fashion.
7. Y2J Arrives, August 9, 1999
For months and months, a mysterious clock counted down to the millennium. When the clock finally struck zero, Chris Jericho debuted in WWE, interrupting The Rock and immediately elevating himself from his midcard WCW days. It’s one of those debuts people still talk about…
6. Hell Froze Over, July 15, 2002
…but it wasn’t as shocking as former WCW President Eric Bischoff being revealed as RAW’s first general manager. Criticize the hug with McMahon all you want, but just seeing Bischoff’s grin on WWE TV was enough for Booker T’s eyeballs to pop out.
5. Pillman’s Got A Gun, November 4, 1996
Perhaps the first time that Raw truly went over the line, Stone Cold invaded Brian Pillman’s home as his former partner sat on his couch clutching a 9 millimeter glock. An F-bomb was dropped and an explosion was heard as the USA Network shat its pants.
4. Austin vs. McMahon, April 13, 1998
An epic bait and switch led to Raw snapping Nitro’s 83-week winning streak in the ratings. The entire two hours were spent building up McMahon’s first match as his confidence grew to accepting Stone Cold’s challenge. WWE didn’t deliver, but it did introduce a new character into the equation and leave the fans salivating over the eventual encounter.
3. The Simulcast, March 26, 2001
It was a once-in-a-lifetime episode as segments of Raw and Nitro were broadcast over both TNN and TNT as McMahon finally conquered his competition and acquired WCW. But…which McMahon? Mwahahahaha!
2. Epic Confrontation, January 19, 1998
Before Mike Tyson became a comedic foil and celebrity cameo, he was the most controversial figure in sports, fresh off biting Evander Holyfield’s ear. In the meantime, Austin had risen as the anti-hero, the profane rebel who flipped off authority and just won the Royal Rumble. The earth shook as the world’s toughest SOB came face-to-face with the baddest man on the planet.
1. Butts In The Seats, January 4, 1999
While Hogan was fingerpoking Kevin Nash on Nitro, Mankind was battling The Rock over the WWE Championship on Raw. The episode was taped, and in an ultimately terrible move by Bischoff, he ordered announcer Tony Schiavone to give away the result along with a sarcastic line about “putting butts in the seats.” Well, that spoiler was enough to entice viewers to check out history in the making, as Mankind achieved his childhood dream of championship glory.
Of course, he had a little help from ol’ Stone Cold, whose arrival drew the biggest pop of all time.