10 Most Iconic Moments in WWE Raw History

Since first hitting our screens in 1993, Monday Night Raw has been an intrinsic part of professional wrestling. The show changed the face of the business, carrying more detailed, weekly storylines to a much wider audience.

Of course, a lot has changed in almost 30 years. At the time of the first Raw, ‘I Will Always Love You’ by Whitney Houston was number one. Bret Hart was WWF Champion. We’d never heard of things like ‘TikTok’ or ’Netflix’ or ‘Chad Gable’.

Some things, however, stay the same. Whitney Houston’s song may no longer rule the charts, but we will always love Monday Night Raw...well, sometimes.

Today is the anniversary of one of Raw's most famous segments, 'Stone Cold' Steve Austin rode the Beer Truck into the arena.

In honour of that momentous occasion, here’s a look back at the 10 Most Iconic Moments in Raw History!

10: This Is Your Life

Where better to begin than with the highest-rated segment in Raw history? Actually, The Rock and Mankind’s famous ‘This Is Your Life’ segment wasn’t the highest-rated Raw segment of all time - that’s a common misconception popularised by the forces of chaos. By which I mean Vince Russo.

The segment saw Mankind host a 20-minute This Is Your Life show in honour of The Rock, his tag team partner in 'The Rock And Sock Connection'. Foley introduced various figures from the Brahma Bull’s past - an old girlfriend, his high school football coach, and so on - only for The Rock to basically be a little bit mean to them.

It was hardly ground-breaking stuff, but it remains a prime example of the wonderful chemistry between loveable loser Mankind and arrogant superstar Rock. It was certainly better than Alexa Bliss and Bayley’s 2017 homage to the segment - the one where it was implied that Bayley had never kissed anyone and was a total big loser.

Despite not actually being Raw’s highest rated segment, Rock and Mankind’s promo entered wrestling folklore. Strangely, the actual highest-rated segment did not - but then it only featured Stone Cold winning the title back from The Undertaker. Nothing important, really.

10: This Is Your Life

Where better to begin than with the highest-rated segment in Raw history? Actually, The Rock and Mankind’s famous ‘This Is Your Life’ segment wasn’t the highest-rated Raw segment of all time - that’s a common misconception popularised by the forces of chaos. By which I mean Vince Russo.

The segment saw Mankind host a 20-minute This Is Your Life show in honour of The Rock, his tag team partner in 'The Rock And Sock Connection'. Foley introduced various figures from the Brahma Bull’s past - an old girlfriend, his high school football coach, and so on - only for The Rock to basically be a little bit mean to them.

It was hardly ground-breaking stuff, but it remains a prime example of the wonderful chemistry between loveable loser Mankind and arrogant superstar Rock. It was certainly better than Alexa Bliss and Bayley’s 2017 homage to the segment - the one where it was implied that Bayley had never kissed anyone and was a total big loser.

Despite not actually being Raw’s highest rated segment, Rock and Mankind’s promo entered wrestling folklore. Strangely, the actual highest-rated segment did not - but then it only featured Stone Cold winning the title back from The Undertaker. Nothing important, really.

9: The Pipebomb

It’s safe to say that without CM Punk’s legendary 2011 pipebomb promo, the current WWE landscape would look a hell of a lot different. We probably wouldn’t have seen Daniel Bryan triumph at WrestleMania 30, or AJ Styles as WWE Champion.

On a straightforward level, Punk’s promo aired the various grievances that he had since leaving the independent scene for WWE. But that doesn’t tell the whole story. It also aired our grievances - the cynical, entitled internet fans who take wrestling far too seriously.

We all do it, don’t pretend you’re better than the rest of us.

Punk’s promo was almost like an anti-WWE message-board rant, but with the benefit of airing on live television. Also, it was being delivered by one of the most charismatic wrestlers in the world, rather than a 15-year-old teenager hyped up on energy drinks.

Punk utterly laid into his employers, and broke several company taboos. He name-dropped other promotions, called out backstage figures like John Laurinaitis, and even referred to Triple H as Vince’s ‘doofus son-in-law’.

Quite simply, it was music to our smarky ears.

9: The Pipebomb

It’s safe to say that without CM Punk’s legendary 2011 pipebomb promo, the current WWE landscape would look a hell of a lot different. We probably wouldn’t have seen Daniel Bryan triumph at WrestleMania 30, or AJ Styles as WWE Champion.

On a straightforward level, Punk’s promo aired the various grievances that he had since leaving the independent scene for WWE. But that doesn’t tell the whole story. It also aired our grievances - the cynical, entitled internet fans who take wrestling far too seriously.

We all do it, don’t pretend you’re better than the rest of us.

Punk’s promo was almost like an anti-WWE message-board rant, but with the benefit of airing on live television. Also, it was being delivered by one of the most charismatic wrestlers in the world, rather than a 15-year-old teenager hyped up on energy drinks.

Punk utterly laid into his employers, and broke several company taboos. He name-dropped other promotions, called out backstage figures like John Laurinaitis, and even referred to Triple H as Vince’s ‘doofus son-in-law’.

Quite simply, it was music to our smarky ears.

8: DX Invades WCW

In all honesty, DX’s ‘invasion’ of WCW wasn’t too outrageous.

It was more like a gang of children hanging around outside the gates of a rival school on their BMXs, occasionally shouting at a teacher and running away into the bushes.

Symbolically, however, the prank meant a great deal. This came in the midst of the Monday Night Wars, and portrayed WWF as a far cooler, edgier product. Triple H and friends rode around outside WCW’s Virginia show on a little tank, shouting about freeing their Kliq buddies from their contracts.

They even convinced several WCW fans to say that WWF was the superior promotion, and generally caused a bit of a nuisance.

It was schoolyard stuff, but that didn’t stop it from becoming a memorable and significant moment. It also featured DX members dressed up as army dudes, and who doesn’t want to see that?

Road Dogg in particular looked really happy, bless his heart.

8: DX Invades WCW

In all honesty, DX’s ‘invasion’ of WCW wasn’t too outrageous.

It was more like a gang of children hanging around outside the gates of a rival school on their BMXs, occasionally shouting at a teacher and running away into the bushes.

Symbolically, however, the prank meant a great deal. This came in the midst of the Monday Night Wars, and portrayed WWF as a far cooler, edgier product. Triple H and friends rode around outside WCW’s Virginia show on a little tank, shouting about freeing their Kliq buddies from their contracts.

They even convinced several WCW fans to say that WWF was the superior promotion, and generally caused a bit of a nuisance.

It was schoolyard stuff, but that didn’t stop it from becoming a memorable and significant moment. It also featured DX members dressed up as army dudes, and who doesn’t want to see that?

Road Dogg in particular looked really happy, bless his heart.

7. Chris Jericho's Debut

1999 saw one of the best debuts ever, as under-appreciated WCW funny-man Chris Jericho strode out onto the Raw stage like an instant main-eventer.

Yes, he was still as obnoxious and hilarious as ever, but it was clear from the segment’s presentation that WWF intended to treat him like the star he deserved to be.

Why was this so apparent?

Well, first of all, Y2J interrupted The Rock. That’s a pretty big deal, considering the Brahma Bull was one of Vince McMahon’s most beloved stars. Maybe second to Austin, but he was about to take time off after being SAVAGELY RUN DOWN by Rikishi at Survivor Series.

Secondly, it’s important to consider the unparalleled charisma of Jericho himself. The newcomer proclaimed himself our saviour, our party host, and implored us to put our “fat little fists” in the air and cheer for him.

The Rock ultimately got the last word, but Jericho had certainly made a huge impact. ‘Raw is Jericho’ indeed.

Not that WWE will admit that anymore...wonder why....

7. Chris Jericho's Debut

1999 saw one of the best debuts ever, as under-appreciated WCW funny-man Chris Jericho strode out onto the Raw stage like an instant main-eventer.

Yes, he was still as obnoxious and hilarious as ever, but it was clear from the segment’s presentation that WWF intended to treat him like the star he deserved to be.

Why was this so apparent?

Well, first of all, Y2J interrupted The Rock. That’s a pretty big deal, considering the Brahma Bull was one of Vince McMahon’s most beloved stars. Maybe second to Austin, but he was about to take time off after being SAVAGELY RUN DOWN by Rikishi at Survivor Series.

Secondly, it’s important to consider the unparalleled charisma of Jericho himself. The newcomer proclaimed himself our saviour, our party host, and implored us to put our “fat little fists” in the air and cheer for him.

The Rock ultimately got the last word, but Jericho had certainly made a huge impact. ‘Raw is Jericho’ indeed.

Not that WWE will admit that anymore...wonder why....

6: Pillman’s Got A Gun

WWE

Without a doubt, Steve Austin’s home invasion of Brian Pillman is one of the most controversial - but also iconic - moments in Monday Night Raw history.

Why? Because Pillman had a gun.

Brian Pillman’s tragic death brought an end to one of the most underrated, compelling careers in professional wrestling. The Cincinnati native bounced between WCW, ECW, and WWF, causing mayhem with his personal brand of loose-cannon anarchy.

His most infamous angle came in 1996, during a November edition of Raw. Having previously been injured by former tag partner Stone Cold Steve Austin, Pillman conducted an interview with Kevin Kelly from his home in Kentucky. Fearing a further attack from Austin, he had surrounded his house with friends.

That didn’t really work, as Austin quickly fought his way inside - only for Pillman to produce a gun and wave it at the Rattlesnake!

To make things more chaotic, the feed cut out, leaving us all wondering what the hell had just happened. When video later returned, Pillman was being subdued, but was clearly heard dropping an F-bomb in the commotion. On live television.

WWF and Pillman later apologised for the whole incident, but it still went down in history as an example of the Attitude Era at its Rawest.

Haha, Rawest. Because this is a list about Raw. Monday Night Raw, the wrestling show.

5: Shane Buys WCW

In 2001, the Monday Night Wars were over, as was wrestling’s time in the mainstream spotlight.

WCW had been bought out by Vince McMahon, and WWE are still yet to face competition on anywhere near a similar scale.

We’re not talking about real life here, though. We’re talking about lovely old kayfabe, where gigantic morticians and boiler-dwelling psychopaths are allowed to murder each other several times without dying.

In March, Raw and Nitro aired at the same time - a historical simulcast. Vince took to the ring in Cleveland, Ohio to gloat over his victory - only to be interrupted by Shane, who was in Florida.

Shane announced that he had bought WCW from under his father’s nose, kicking off the most infamous storyline in WWE history - the Invasion Angle.

Fast forward a few months, and we have WWF hero Steve Austin leading the invading forces, DDP stalking Undertaker’s wife, and Kurt Angle blasting everyone with milk because he’s Kurt Angle. But it all started during that simulcast.

5: Shane Buys WCW

In 2001, the Monday Night Wars were over, as was wrestling’s time in the mainstream spotlight.

WCW had been bought out by Vince McMahon, and WWE are still yet to face competition on anywhere near a similar scale.

We’re not talking about real life here, though. We’re talking about lovely old kayfabe, where gigantic morticians and boiler-dwelling psychopaths are allowed to murder each other several times without dying.

In March, Raw and Nitro aired at the same time - a historical simulcast. Vince took to the ring in Cleveland, Ohio to gloat over his victory - only to be interrupted by Shane, who was in Florida.

Shane announced that he had bought WCW from under his father’s nose, kicking off the most infamous storyline in WWE history - the Invasion Angle.

Fast forward a few months, and we have WWF hero Steve Austin leading the invading forces, DDP stalking Undertaker’s wife, and Kurt Angle blasting everyone with milk because he’s Kurt Angle. But it all started during that simulcast.

4: Vince Fakes His Own Death

This angle stems from Vince being sad that he’d lost the ECW Championship at One Night Stand - a sentence that sounds like it was written by one of those funny automated Twitter bots.

A subsequent episode of Raw was branded ‘Vince McMahon appreciation night’, a show where everybody was very unappreciative of Vince McMahon. Despondent, he left the ring and made the long walk to his limousine, passing numerous roster members along the way. It was very suspicious, almost like we were supposed to suspect that somebody had bad things in store for Vince).

Many speculated that it was Paul London, who smiled weirdly as Vince walked past - but apparently he just did that because he felt like it.

Finally Vince reached the limo, and it shockingly exploded - apparently killing the owner of WWE.

Unfortunately, we were never able to find out what happened next. The tragic and horrifying circumstances surrounding the death of Chris Benoit caused WWE to wisely call off the whole thing, revealing that the culprit was going to be Vince himself.

What? Why!? It doesn’t matter.

4: Vince Fakes His Own Death

This angle stems from Vince being sad that he’d lost the ECW Championship at One Night Stand - a sentence that sounds like it was written by one of those funny automated Twitter bots.

A subsequent episode of Raw was branded ‘Vince McMahon appreciation night’, a show where everybody was very unappreciative of Vince McMahon. Despondent, he left the ring and made the long walk to his limousine, passing numerous roster members along the way. It was very suspicious, almost like we were supposed to suspect that somebody had bad things in store for Vince).

Many speculated that it was Paul London, who smiled weirdly as Vince walked past - but apparently he just did that because he felt like it.

Finally Vince reached the limo, and it shockingly exploded - apparently killing the owner of WWE.

Unfortunately, we were never able to find out what happened next. The tragic and horrifying circumstances surrounding the death of Chris Benoit caused WWE to wisely call off the whole thing, revealing that the culprit was going to be Vince himself.

What? Why!? It doesn’t matter.

3. Vince's First Stunner

Everyone remembers their first, right?

For many years, it felt as though Stone Cold stunned Vince McMahon every other week - but the first ever Stunner to Vince was a monumental occurrence.

In September 1997, Raw was broadcast from Madison Square Garden for the first time ever. Something big was needed to mark the occasion, and that came in the form of one of the worst Stunners in recorded history.

Thankfully, despite Vince’s weird floppy fish sell, the enormous nature of the moment overshadowed its dodgy execution.

To prevent this list from being almost entirely Steve Austin, I’ve had to omit a few other legendary Stone Cold moments from Raw. Here they are very quickly:

Austin and Tyson, ‘it’s me Austin!’, jumping off the zamboni, Bang 3:16, crashing Undertaker’s wedding, and the time he took his ball and went home.

3. Vince's First Stunner

Everyone remembers their first, right?

For many years, it felt as though Stone Cold stunned Vince McMahon every other week - but the first ever Stunner to Vince was a monumental occurrence.

In September 1997, Raw was broadcast from Madison Square Garden for the first time ever. Something big was needed to mark the occasion, and that came in the form of one of the worst Stunners in recorded history.

Thankfully, despite Vince’s weird floppy fish sell, the enormous nature of the moment overshadowed its dodgy execution.

To prevent this list from being almost entirely Steve Austin, I’ve had to omit a few other legendary Stone Cold moments from Raw. Here they are very quickly:

Austin and Tyson, ‘it’s me Austin!’, jumping off the zamboni, Bang 3:16, crashing Undertaker’s wedding, and the time he took his ball and went home.

2: The Beer Truck

Okay, so there was one Stone Cold moment that probably does deserve a separate entry of its own - and that’s the Corporation’s beer bath.

Nothing sums up the anarchy and excitement of the Attitude Era quite like this classic Raw moment. With the evil collective of Vince, Shane, and WWF Champion The Rock gloating in the ring, a mischievous Austin drove a beer truck all the way down to ringside.

After arguing with the heels for a little while, Stone Cold created chaotic magic, unravelling a hose from the truck and dousing the Corporation in beer.

It was a silly moment, truth be told - but wrestling is silly, and this moment reminded us of that in the most entertaining way possible.

2: The Beer Truck

Okay, so there was one Stone Cold moment that probably does deserve a separate entry of its own - and that’s the Corporation’s beer bath.

Nothing sums up the anarchy and excitement of the Attitude Era quite like this classic Raw moment. With the evil collective of Vince, Shane, and WWF Champion The Rock gloating in the ring, a mischievous Austin drove a beer truck all the way down to ringside.

After arguing with the heels for a little while, Stone Cold created chaotic magic, unravelling a hose from the truck and dousing the Corporation in beer.

It was a silly moment, truth be told - but wrestling is silly, and this moment reminded us of that in the most entertaining way possible.

1: Mankind Wins The WWF Championship

It’s hard to argue against the notion that Mankind’s victory, broadcast on January 4, 1999, is one of the most iconic moments in wrestling history - let alone Raw history.

It wasn’t anything too out of the ordinary, in the grand scheme of things. With the help of a returning Steve Austin, Mankind was able to upset The Rock and win the WWF Championship - an exciting moment for sure, but that doesn’t explain why it was so ground-breaking.

Remember, this match is looked back on as the turning point in the Monday Night Wars.

Its iconic status has more to do with the poetic nature of the incident. Over on WCW Nitro, Tony Schiavone attempted to spoil the result of the pre-taped match, preventing fans from changing the channel. Instead, they did just that, turning over to Raw en masse to watch Foley’s unlikely triumph.

Oh Schiavone, you silly silly man.

1: Mankind Wins The WWF Championship

It’s hard to argue against the notion that Mankind’s victory, broadcast on January 4, 1999, is one of the most iconic moments in wrestling history - let alone Raw history.

It wasn’t anything too out of the ordinary, in the grand scheme of things. With the help of a returning Steve Austin, Mankind was able to upset The Rock and win the WWF Championship - an exciting moment for sure, but that doesn’t explain why it was so ground-breaking.

Remember, this match is looked back on as the turning point in the Monday Night Wars.

Its iconic status has more to do with the poetic nature of the incident. Over on WCW Nitro, Tony Schiavone attempted to spoil the result of the pre-taped match, preventing fans from changing the channel. Instead, they did just that, turning over to Raw en masse to watch Foley’s unlikely triumph.

Oh Schiavone, you silly silly man.