Top 20 Monday Night Raw Moments Ever
Stone Cold Steve Austin
20. Ric Flair’s Emotional Retirement Speech (March 31, 2008)
One night after losing to Shawn Michaels at WrestleMania XXIV, Ric Flair delivered a tearful farewell on Raw. The entire WWE roster filled the stage as Flair thanked the fans for his 36-year career. Superstars like The Undertaker, Triple H, and Chris Jericho embraced him in a powerful send-off. The crowd chanted “Thank you, Flair!” for several minutes uninterrupted. It remains one of the most heartfelt and dignified goodbyes in WWE television history.
19. 1-2-3 Kid Upsets Razor Ramon (May 17, 1993)
A little-known newcomer named The Kid faced Razor Ramon on Monday Night Raw in what seemed a squash match. In a shocking finish, The Kid dodged a move and rolled Ramon up for a quick three-count. The audience erupted, witnessing an authentic underdog victory. The upset launched The Kid — later known as X-Pac — into stardom. It showed that Raw could deliver real surprises and make new stars instantly.
18. Braun Strowman Flips Ambulance with Roman Reigns Inside (April 10, 2017)
In a backstage assault, Braun Strowman brutally attacked Roman Reigns, throwing him off a stretcher and into walls. The assault culminated in Strowman tipping over an entire ambulance with Reigns inside, using only his strength. The segment was executed with minimal CGI, shocking fans with its realism. It elevated Strowman’s “Monster Among Men” persona overnight. The spectacle became a viral highlight across social media and sports outlets.
17. Mankind Attacks Jim Ross during Interview (April 1, 1996)
In a pre-taped segment, Jim Ross interviewed newcomer Mankind to introduce him to WWE audiences. The conversation turned dark as Mankind spoke about pain and rejection before violently attacking Ross with the Mandible Claw. The disturbing scene showcased Foley’s psychological complexity and unpredictability. It marked a shift toward more serious, character-driven storytelling on Raw. The moment cemented Mankind as a legitimate and unsettling presence.
16. Test’s Wedding to Stephanie McMahon Interrupted by Triple H (November 29, 1999)
During the live televised wedding of Test and Stephanie McMahon, Triple H interrupted to reveal shocking footage of a Vegas drive-thru wedding. The clip showed him marrying an unconscious Stephanie after drugging her earlier that night. The revelation instantly turned the McMahon family storyline upside down. Stephanie aligned with Triple H, forming the infamous McMahon-Helmsley Regime. It became one of Raw’s most pivotal soap-opera-style twists.
15. Daniel Bryan Occupies Raw (March 10, 2014)
In Memphis, Daniel Bryan led a ring full of fans chanting “Yes!” to protest The Authority’s refusal to give him a WrestleMania opportunity. The “Occupy Raw” movement saw hundreds fill the ring, forcing Triple H and Stephanie McMahon to back down. The crowd’s energy was deafening, symbolizing true fan power. WWE had no choice but to insert Bryan into the WrestleMania XXX main event. The segment perfectly captured the modern era’s audience-driven influence on storylines.
14. Vince McMahon’s Limousine Explosion (June 11, 2007)
At the end of a strange, silent episode of Raw, Vince McMahon entered his limousine — which suddenly exploded seconds later. The shocking visual left fans believing the chairman had been killed off on television. Though the storyline was abandoned due to real-life events, it remains one of WWE’s most elaborate staged moments. The explosion marked WWE’s experimentation with cinematic finales and scripted shock value during the 2000s. Even years later, it’s remembered as one of the show’s boldest cliffhangers.
13. The Nexus Debuts (June 7, 2010)
Led by Wade Barrett, eight NXT rookies invaded Raw during John Cena’s main event match. They destroyed the ring, announcers, and several wrestlers, leaving chaos everywhere. Their coordinated attack on Cena and CM Punk stunned the live audience and disrupted the show completely. The debut established The Nexus as a dominant rogue faction and introduced names like Daniel Bryan and Ryback to the main roster. It was one of WWE’s most impactful debuts of the decade.
12. Stone Cold Throws the Intercontinental Title Into the River (December 15, 1997)
Following his feud with The Rock, Stone Cold rejected his Intercontinental Championship by tossing it into the San Antonio River. He declared he didn’t need the title and was focused on bigger goals, especially the WWE Championship. The act captured his defiant character perfectly. The Rock’s attempt to retrieve the title later became another comedic highlight. It showcased WWE’s growing investment in cinematic storytelling and character-driven moments on Raw.
11. Kurt Angle Blasts The Alliance with Milk (August 20, 2001)
Kurt Angle parodied Austin’s iconic beer truck moment during the Invasion storyline. Driving a milk truck to the ring, he sprayed The Alliance members, including Steve Austin, with cartons and hoses of milk. The crowd erupted as Angle celebrated with a milk toast atop the truck. The segment mixed comedy with nostalgia, showing Angle’s unique charisma. It remains one of the funniest and most replayed moments in Raw’s history.
10. Stone Cold Stuns Vince McMahon for the First Time (September 22, 1997)
At Madison Square Garden, Vince McMahon tried to calm Stone Cold Steve Austin during a segment regarding his neck injury. Austin responded by delivering the first-ever Stone Cold Stunner to the WWE Chairman. The stunned silence that followed quickly turned into chaos as security rushed the ring. That single act birthed one of the greatest rivalries in wrestling history. It set the stage for years of rebellion and redefined WWE’s creative direction in the Attitude Era.
9. Shane McMahon Buys WCW (March 26, 2001)
In a historic simulcast, Vince McMahon announced WWE’s purchase of WCW live from Cleveland while a Nitro broadcast aired from Panama City. In a twist, Shane McMahon appeared on the WCW broadcast to reveal he had bought the company instead. The storyline surprise merged the two rival promotions under one banner. It officially marked the end of the Monday Night Wars after six years of fierce competition. The moment was both symbolic and monumental for wrestling’s business history.
8. Mike Tyson and Stone Cold Steve Austin Brawl (January 19, 1998)
Mike Tyson’s guest appearance on Raw was meant to announce his WrestleMania involvement, but Stone Cold Steve Austin interrupted. Their confrontation quickly escalated into a chaotic brawl, with security and officials trying to separate them as Tyson shoved Austin. The segment drew massive mainstream attention, bridging sports and entertainment. It led to Tyson’s alignment with D-Generation X and Austin’s rise as WWE’s anti-hero. This crossover moment brought WWE back into pop culture relevance after years of WCW dominance.
7. DX Invades WCW (April 27, 1998)
D-Generation X, Triple H, X-Pac, Billy Gunn, Road Dogg, and Chyna, drove a camouflaged jeep with a mounted cannon to a WCW taping in Norfolk, Virginia. They confronted fans outside and mocked the rival promotion on live television. The risky stunt blurred real competition with entertainment, daring WCW to respond. WWE cameras captured everything, and the footage became iconic. The segment symbolized WWE’s defiant spirit during the Monday Night Wars and helped shift fan perception in their favor.
6. Chris Jericho’s WWE Debut (August 9, 1999)
A cryptic “Countdown to the Millennium” clock had been appearing on WWE screens for weeks, ending during a Rock promo in Chicago. When the countdown hit zero, Chris Jericho made his first WWE appearance, instantly confronting The Rock with his trademark arrogance. The debut mixed mystery, humor, and star presence, immediately setting Jericho apart. His promo was witty and confident, drawing a huge reaction from the crowd. It remains one of the most celebrated debuts in Raw history.
5. Seth Rollins Betrays The Shield (June 2, 2014)
After The Shield defeated Evolution at Payback 2014, no one expected their unity to collapse the next night on Raw. Triple H introduced Seth Rollins as “Plan B,” and Rollins attacked Roman Reigns and Dean Ambrose with a steel chair. The shocking betrayal ended one of WWE’s most dominant factions. It launched Rollins’ solo career and defined his character as “The Architect.” The turn was executed with perfect timing and remains one of the most memorable modern betrayals on Raw.
4. Mankind Wins the WWE Championship (January 4, 1999)
In a pre-taped Raw Is War episode from Worcester, Massachusetts, Mankind defeated The Rock to win his first WWE Championship. Stone Cold Steve Austin interfered in the closing moments, hitting The Rock with a chair and helping Foley secure the pin. WCW famously spoiled the result live on Nitro, causing hundreds of thousands to switch channels and witness Mankind’s victory. The moment not only crowned an unlikely champion but also shifted the balance in the Monday Night Wars. It marked the night WWE overtook WCW in ratings for good.
3. “This Is Your Life” Segment with The Rock and Mankind (September 27, 1999)
Mankind surprised The Rock with a “This Is Your Life” celebration, featuring cameos from The Rock’s old teachers, ex-girlfriend, and coach. The long, unpredictable segment mixed humor and nostalgia, with The Rock’s reactions adding to its charm. Despite running nearly 30 minutes, it achieved the highest rating in Raw history at 8.4. The segment highlighted the comedic chemistry between the two stars. It remains the benchmark for successful sports entertainment storytelling.
2. CM Punk’s “Pipe Bomb” Promo (June 27, 2011)
During a live episode of Raw in Las Vegas, CM Punk sat cross-legged on the stage and unleashed a brutally honest promo directed at WWE’s top brass. He called out Vince McMahon, Triple H, and even The Rock, expressing frustrations with how the company favored certain stars. The “Pipe Bomb” blurred lines between reality and storyline, catching viewers completely off guard. It reignited mainstream interest in WWE and made Punk the face of a new, outspoken generation. His mic work that night is still studied as one of the greatest promos in wrestling history.
1. Stone Cold Steve Austin’s Beer Bath on Vince McMahon (March 22, 1999)
On the road to WrestleMania XV, Stone Cold Steve Austin stormed into the arena driving a beer truck during a Corporation segment. He grabbed a hose and drenched Vince McMahon, Shane McMahon, and The Rock in front of a roaring crowd in Albany, New York. The moment was unscripted chaos at its best, highlighting Austin’s anti-authority persona. Fans erupted as McMahon visibly slipped and flailed, creating one of WWE’s defining visuals. It remains one of the most replayed moments in Raw history and a symbol of the Attitude Era’s rebellious energy.
