The 20 Most Legendary "Monday Night Raw" Moments

Celebrate the 25th anniversary of WWE's "Monday Night Raw" with this trip down memory lane.
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Earlier this week, SI.com celebrated the upcoming 25th anniversary edition of “Monday Night Raw” by revealing the seven most outrageous storylines in the show’s history

The show debuted Jan. 11, 1993 from New York City's Manhattan Center. This week's "Raw" will take place at both the Manhattan Center and Barclay's Arena, with a slew of Hall of Fame superstars making their return for the show.

We’re continuing the celebration today by looking back at the most legendary moments over “Raw’s” 25 years on the air.

1. May 17, 1993: 1-2-3 Kid beats Razor Ramon

Back in this era, a jobber never beat a superstar. That changed when the 1-2-3 Kid, better known later as X-Pac/Sean Waltman, pulled the upset against the Bad Guy.

2. Sept. 30, 1996: Jim Ross turns heel, brings back "Diesel" and "Razor Ramon" 

Kevin Nash/Diesel and Scott Hall/Razor Ramon leaving WWE for WCW is an iconic event in pro wrestling history since it led to the formation of the NWO. The WWE, reeling from the defections and the success WCW had with the duo, decided to turn broadcaster Jim Ross heel and have him announce the returns of Diesel and Razor since the characters were intellectual property of the WWE. This is notable not for being a success, but for the bizarre decision and huge flop the storyline turned out to be.

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3. Sept. 22, 1997: Stone Cold Steve Austin stuns Vince McMahon for first time

Perhaps the biggest feud in WWE history went to another level on this night when McMahon, who was then just an announcer, not the WWE owner, to many wrestling fans, took the first of many Stone Cold Stunners in Madison Square Garden.

4. Nov. 17, 1997: "Bret Screwed Bret"

Following the infamous Montreal Screwjob, McMahon explained why he did what he did and buried Hart for not agreeing to drop his title to Shawm Michaels before heading to WCW.

5. Jan. 19, 1998: Tyson and Austin!

This was a monumental moment for the WWE in terms of getting crossover appeal by having Tyson appear on "Raw." Having Austin confront Tyson took Austin to new heights in terms of being over. 

6. April 27, 1998: DX invades WCW

With "Raw" and "Nitro," taking place miles apart, HHH, the Road Dogg, Billy Gunn, X-Pac and Chyna drove a tank to the WCW arena looking for a confrontation.

7. Sept. 28, 1998: Austin beer truck

The image of Stone Cold driving a beer truck to ringside and spraying Vince and Shane is one of the most iconic in WWE history.

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8. Jan. 4, 1999: Mick Foley wins WWE title

Every wrestling fan knows the story. "Raw" was taped at this point and "Nitro," which was live gave away the result of the match. Immediately, 600,000 people flipped over from "Nitro" to "Raw" to watch Mrs. Foley's baby boy win his first WWE title. And the wrestling ratings game changed forever.

9. Aug. 9, 1999: Chris Jericho debuts on "Raw"

This was built up for weeks and then the Titantron finally unleashed the countdown and Jericho interrupted The Rock as the two engaged in one of the most memorable WWE promos ever.

10. Sept. 27, 1999: "This Is Your Life"

Mankind wanted to honor his "Rock-and-Sock Connection" partner, so he celebrated The Rock in one of the longest and highest-rated segments in "Raw" history.

11. March 26, 2001: "Raw"-"Nitro" simulcast

Vince McMahon won the war with WCW and purchased the company. The result was a surreal simulcast of both Monday night shows, which would be the last "Nitro" ever.

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12. May 21, 2001: Chris Jericho and Chris Benoit beat Steve Austin and Triple H for the Tag Team Titles

This is significant for many reasons: 1) At this point in the time, there was a perception that smaller wrestlers would never win over Vince McMahon. So having two of the smaller guys go over two of the top guys in the company was shocking; 2) HHH tore his quad during this match but kept going; 3) The crowd was as hot as any you'll see; 4) Jim Ross damn near lost his mind calling this match.

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13. July 15, 2002: Vince McMahon names Eric Bishoff "Raw" GM

Nobody would've ever expected McMahon to do business with his mortal enemy, but Vince is always full of surprises, as she showed here.

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14. Jan. 4, 2010: Bret Hart returns

Few thought it would ever happen after the "Montreal Screwjob," but the Hitman finally returned to the company more than 12 years after that event and buried the hatchet with Shawn Michaels, who admitted to being in on the plan, in the middle of the ring.

15. June 7, 2010: The Nexus invade "Raw"

The stable of NXT wrestlers crashed the main event between John Cena and CM Punk and took out both superstars, announcers, referees, officials and destroyed the ring, the set and everything else.

16. June 27, 2011: CM Punk pipebomb

When you cut a promo and some fans think it's legit and not scripted, you've done your job. Punk pulled back the curtain and unloaded on the WWE in such an honest way many people thought he was "shooting."

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17. Dec. 9, 2013: Daniel Bryan fans hijack "Raw"

HHH brought a bunch of former WWE champs to the ring, including Bryan, while he cut a promo. Bryan's presence led to the crowd continually chanting his name and taking over the show. Triple H was unable to continue his promo for about two straight minutes.

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18. March 10, 2014: YES movement takes over "Raw"

The previous incident saw the fans take over "Raw." On this night, it was Bryan who took over the show.

19. June 2, 2014: The Shield break up

Few expected Seth Rollins to be the Shield member to turn heel, so it was a huge surprise when he unleashed a vicious chair shot on Roman Reigns.

20. Feb. 22, 2016: Shane returns

It's pretty much impossible in this day and age of social media for the WWE to pull of a truly legitimate shocking moment. So when Shane McMahon appeared on "Raw" after a six-year absence, it was a real, "Wow," moment because nobody knew it was happening.


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Jimmy Traina
JIMMY TRAINA

Jimmy Traina is a staff writer and podcast host for Sports Illustrated. A 20-year veteran in the industry, he’s been covering the sports media landscape for seven years and writes a daily column, Traina Thoughts. Traina has hosted the Sports Illustrated Media Podcast since 2018, a show known for interviews with some of the most important and powerful people in sports media. He also was the creator and writer of SI’s Hot Clicks feature from 2007 to '13.