As the “longest episodic weekly running drama,” Monday Night Raw has the arduous task of trying to outdo itself week after week. For over 25 years, the WWE has managed to walk that tightrope, too. While they might not always have the best segments, usually the company does have the best intentions - to entertain the fans. Much like the facts of life, WWE fans take the good with the bad. But the WWE Universe had some of the most die-hard fans of any genre.
Those fans have an elephant-like memory for a lot of terrible moments in Raw history and there are a whole bunch over the years, enough to fill several lists. But here are the 10 Cringiest Moments In WWE Raw History.
10 Katie Vick
You all knew this would be here, you all threw up in your mouth a little when you watched it, so might as well get it out of the way early. Once upon a time on Monday Night Raw, Triple H dressed up as Kane and proceeded to make it with a corpse, or a mannequin representing a corpse, or who the heck knows?! It was supposed to be a segment to drum up the drama between Triple H and Kane, and it fell horrifically and miserably flat.
9 Who Killed Mr. McMahon?
The original idea for “Mr. McMahon Appreciation Night” was to kick off a fairly long storyline ala Dallas’ “Who shot J.R.? Where fans would be guessing as to who was behind blowing up Vince’s limo.
Real-life tragedy completely ended this storyline abruptly, but this one night ended in an angle that had a lot of real-life first responders called to the fake explosion angle. It all seemed to appeal to the lowest denominator.
8 Mae Young Gives Birth
Sexual Chocolate Mark Henry and the indomitable Johnnie Mae Young seemed so mis-matched that the only way the pairing would have worked is if they both plunged in full steam ahead. Which is what they both did, even as Mae announced to the world “we’re pregnant!” If a septuagenarian getting knocked up wasn’t quirky enough, what exactly and how exactly would this angle actually end? Did anyone expect her to walk onstage at Raw with a little bundle of chocolate joy?! Nope, just an ooey, gooey gross hand.
7 Rosie Vs. Donald
Moments like this are proof positive that the WWE is all for an audience of one - Vince McMahon. He was front and center to watch two poor imitations of imitations of talk show host Rosie O’Donnell and then host of The Apprentice, Donald Trump. The real-life counterparts had been locked in a heated war of words all over the media. Naturally, the Chairman wanted to see a “match” between the two. This makes the mixed tag that featured Jackie Gayda look like a mat classic.
6 The “Outsiders” Return
With Hall and Nash firmly in WCW but were mimicking some of their old character’s respective mannerisms. WWE made a slick ploy to get them to cease and desist. They started promoting that both Diesel and Razor Ramon were gearing up for a big return. It all turned out to be a ruse orchestrated by JR turning heel and bringing in two fairly convincing lookalikes – Rick Bognar as Razor and Glen Jacobs as Diesel. The move helped WWE win a lawsuit against WCW but was met with immediate boos and jeers from the crowd.
5 Degrading Trish
What hasn’t been said about how tawdry and wrong this segment was? Trish was already running around with Vince McMahon. But one week on Raw, the Chairman decided that he was done playing with his toy and dumped her by pitting her against William Regal and dumping slop on her.
One week later, McMahon forced her to strip to her skivvies and bark like a dog. The segment is almost always thought of as not just one of the worst segments in Raw history, but WWE history in general.
4 This Is Your Life
While the This Is Your Life segment between Mankind and the Rock is generally regarded to as comedic gold, the WWE fell right on its face when they tried to do it again nearly twenty years later. When Alexa Bliss and Bayley were getting ready for their Extreme Rules match, Bliss presented the then-Hugger with a terrible and groan-inducing segment that had the fans in attendance chanting “boring” and “delete.”
3 Bobby, Lana, And Rusev, Oh My
The latest and greatest of WWE blunders on Raw is the sordid love triangle between Rusev, Lana, and Bobby Lashley. These segments have all been pretty abysmal and poorly received by plenty of fans and fellow wrestlers alike. Between this storyline and the martial troubles of the Kanellis,’ it seems that someone on the Raw writing crew likes to see marriages crumble in front of billions of TV viewers every week. Sure, they’re all playing characters, but when the storylines aren’t good, it’s no wonder a lot of these guys are asking for their releases.
2 “It’s Not My Fault”
The Kane and Lita storyline was ridiculous enough to begin with – he won the right to marry her after defeating her then-boyfriend, Matt Hardy in a “Til Death Do Us Part” match.
Now that she was forced to marry the Devil’s Favorite Demon, she got pregnant with his demon seed. Then Gene Snitsky unfortunately caused Lita to miscarriage. He then proceeded to declare that “it’s not my fault,” and punted a fake baby into the stands.
1 Dr. Heiney
While JR has always been ribbed on by the Chairman, this one seemed particularly insensitive. The man who worked tirelessly for you and your business to the point that he suffered Bell’s Palsy and needed an emergency colon surgery. The Boss’ twisted sense of humor came through in a pinch. Vince thought it was a hilarious to mock JR’s ordeal by becoming Dr. Heiney and proceeded to yank all kinds of things out of the other end of JR’s black hat, up to an including his BBQ Sauce, and his own head.