Top 10 Greatest WWE Monday Night Raw Moments

You can't celebrate the greatest moments of “Monday Night Raw” without going back to where it all began. On January 11, 1993, WWE (then WWF) aired the first-ever episode of Raw live from the Manhattan Center in New York City. This revolutionary broadcast introduced a fresh, intimate live format that greatly contrasted with the pre-taped wrestling programs of the era. With a combination of high-energy matches and iconic characters like Razor Ramon and The Undertaker, this inaugural episode set the tone for “Raw,” marking the beginning of a cultural phenomenon that would grow into the juggernaut it is today.

Mark this one under the column “Hell has frozen over.” You see, Eric Bischoff not only led rival WCW’s charge against WWE during the “Monday Night Wars,” but he came as close as anyone in putting the company out of business. So, when Eric smugly returned as the General Manager of “Raw,” fans couldn’t believe their eyes. Making his stunning debut with a big embrace with Vince McMahon no less, Bischoff’s shocking presence on WWE television represented a paradigm shift. He would go on to exude a sense of unpredictability that thrived throughout his tenure - adding a welcome new dimension to “Raw's” narrative.

By 2014, The Shield was the most dominant force in WWE. They were a trio of arguably the toughest men on the roster who routinely fought what they perceived as “injustices.” So, when Seth Rollins maliciously swung a steel chair at his partners Roman Reigns and Dean Ambrose and aligned himself with The Authority, fans were left speechless. This betrayal was one of those deftly executed moments that flipped the switch and cemented Seth Rollins as a cunning competitor. It still stands as one of the most shocking moments in “Raw” history, proving that anything can, and likely will, happen in WWE’s unpredictable world.

No episode of "Raw" has ever descended into as much chaos as the one that aired on June 7, 2010. The shocking emergence of the Nexus turned the wrestling world on its head, leaving serious carnage in their wake. The group of NXT rookies, led by Wade Barrett, stormed the ring and laid waste to everyone and everything in their path – including the WWE’s Superman equivalent, John Cena. Ripping apart the ring and assaulting commentators, the Nexus showcased their hunger for dominance in a big way. And while the promising angle fizzled in the weeks that followed, there’s no denying the air of pandemonium the group brought to “Raw” on this fateful night.

Speaking of monumental arrivals… Leading up to this iconic moment in August of 1999, weeks of mysterious “countdown clock teases” appeared on WWE programming. Interrupting The Rock during a promo, the countdown once again took center stage. This time however, it would hit zero, revealing the “Millennium Man” as none other than Chris Jericho. The former WCW mainstay had officially jumped ship to the competition, and in doing so, immediately established himself as a major player. The debut wasn’t just memorable – it was iconic. In fact, it reinforced the idea that “Raw” was the premier destination for star-making moments in sports entertainment.

Talk about a turning point. January 4, 1999 was a night of redemption and triumph, as this was the episode of “Raw” where Mick Foley defeated The Rock to win the WWE Championship. With more than a little help from Stone Cold Steve Austin, Foley’s victory was met with one of the loudest crowd reactions in “Raw” history – and that’s saying something. For WWE diehards, the moment was made even sweeter by WCW’s infamous blunder of spoiling the result - which backfired spectacularly and had their viewers switching the channel to see the big win on “Raw”. It was a feel-good moment that set the WWE back on the path of prominence.

To boost visibility and ratings during the infamous “Attitude Era,” WWE brought in boxing heavyweight Mike Tyson to shake things up. And so, on January 19, 1998, the “Baddest Man on the Planet” appeared on “Raw” - only to find himself in the middle of a head-to-head confrontation with Stone Cold Steve Austin. The explosive and chaotic brawl that followed set the stage for Tyson’s involvement at WrestleMania where he’d take on the role of a “special enforcer” in Austin’s match against Shawn Michaels. The segment on “Raw” however, drew interest (and eyeballs) from around the world to WWE's programming and solidified Austin as a must-see wrestling anti-hero.

A June 2011 episode of “Monday Night Raw” saw CM Punk grab a microphone and deliver one of the (ahem) rawest promos in professional wrestling history. Now known as the "Pipebomb heard round the world,” Punk expertly blurred the lines of what was real and not. He openly criticized his place within the WWE and called out the likes of Vince McMahon – all while sitting cross-legged on the stage. By airing his grievances, Punk managed to resonate with disenfranchised fans of the company. He also set a new standard for wrestlers breaking their silence. This moment wasn’t just a typical promo - it was a cultural phenomenon that still resonates to this day.

March 26, 2001, was a historic night in professional wrestling. It was the night that Vincent K McMahon revealed to the world that he had acquired his competition, WCW. However, during a simulcast between “Raw” and WCW’s final broadcast of “Nitro,” Vince’s relentless gloating was interrupted by his own son, Shane McMahon. In one of the most shocking moments of the “Monday Night Wars,” Shane proceeded to reveal that he had purchased WCW – right under his father’s nose. The moment, of course, marked the end of an era and the beginning of WWE’s dominance over the wrestling landscape.
Before we unveil our top pick, here are some honourable mentions.
The 1-2-3 Kid Upsets Razon Ramon
Serves as one of the earliest examples of “Raw’s” exciting unpredictability

A history-making first-ever women’s championship main event on “Raw”

WWE sends in the troops while the “Monday Night War” was at its boiling point

The “Billion-Dollar Princess” gets a most unexpected wedding surprise

For many years, WWE was defined by the legendary “boss VS employee” feud between Vince McMahon and Stone Cold Steve Austin. And while the pair took part in an assortment of entertaining segments, it was Austin’s “beer bath” to McMahon and his cronies that stands as the most iconic. On the March 22, 1999 episode of “Raw,” Austin interrupted Vince, Shane, and The Rock’s corporate celebration by driving a beer truck down to ringside. “The rattlesnake” then proceeded to hose them down with an abundance of ale. It was the perfect encapsulation of Austin’s rebellious spirit and remains one of the most entertaining segments in WWE history. Cheers to that!
How long have you been watching WWE’s flagship Monday night program? What is your all-time favorite match or moment from “Raw”? Share your thoughts in the comments below.