In its heyday, MTV was a bastion for all that was right and wrong with music at the time. Many artists embraced the new medium with open arms, while others shunned the idea as grotesque and superficial, believing that their work should be heard and not seen. It was no small wonder that most of those artists looked like something you’d find in a live bait shop.  Right or wrong, making videos became an essential way of connecting with audiences. Some were great…some were excrescent. The clips below exemplify the worst of the worst…or should I say – the most cringeworthy videos of all time!

“Say, Say, Say” – Paul McCartney and Michael Jackson
Maximum cringe-osity at 3:00 into the video.

“Just look at my face these tears ain’t dryin’,” damn straight, tears of laughter. This video is replete with cringe, but the little moment when Paul playfully dabs a bit of cream on MJ’s cheeks is the cringe-iest. The gloved one just gets this look of rapture on his face, as if he’s thinking, ‘Ohhh… if only that was ANOTHER kind of cream’.

“Party All the Time” – Eddie Murphy 
Maximum cringe-osity at 2:49 into the video

Eddie Murphy proves beyond the shadow of a doubt that he’s not a five tool player in this horrific display of inept warbling. The whole song almost seems like a parody, but unfortunately Murphy’s serious as a heart attack. The final cringe-y blow comes when Rick James wills Eddie to hit the final high note in the song, it’s just so dramatic, cracks me up every time!

“You’re a Friend of Mine” – Clarence Clemons featuring Jackson Browne
Maximum douchosity at 3:32 into the video

GET A ROOM ALREADY!! Seriously, watching these two make goo goo eyes at each other like a couple of lovesick klutzes is positively barf inducing. To tell you the truth, the whole video is mega cringe, between Daryl Hannah lounging around like a tool, making her ‘art’ and Browne and Clemons’ practically sodomizing each other on camera, it’s very tough to choose the ‘cringe de grace’, but if I had to pick it would be the little ‘hen pecking’ dance they do together. I think this video effectively ended the ‘big man’s’ solo aspirations.

“Too Late for Goodbyes” – Julian Lennon
Maximum cringe-osity at 1:34 into the video

This mess is just so actively WRONG. Sam Peckinpah (yes you heard me correctly, legendary director of Bring me the Head of Alfredo Garcia and The Wild Bunch) shot the video for this jaunty little pop gem and inexplicably creeped it up to cringe factor five by casting a seeming mental patient dancing an avant garde jig in the periphery. Every scene he’s in is total cringe-o-rama, but the one I chose is the cringe-iest.

“Mmmm Mmmm Mmmm Mmmm” – The Crash Test Dummies
Maximum cringe-osity at 2:42 into the video

This song was one of the major atrocities to come out of the grunge era. Featuring ponderous lyrics and one of the most annoying choruses of all time, I remember wanting to kick my TV in every time it came on. The video just kind of awkwardly ambles forth, drenched in that ubiquitous ‘90s mood lighting that was so popular back then. The cringe was mostly perpetrated by the lead singer, Brad Roberts, whose rubber-faced mugging just makes you want to sock him in the kisser. Seriously, I just wanna clop him in the nuts with a sack full of quarters to raise that retching baritone of his up a few octaves. The moment I chose, he contorts his punim into a particularly irritating permutation.

“Telephone” – Lady Gaga featuring Beyonce
Maximum cringe-osity at 5:00 into the video

This pretentious, masturbatory, whack-fest is filled to the brim with cringe. Whether it be Gaga’s clucky dancing, performed with all the grace of an arthritic duck, or the insufferably lame Tarantino/Thelma and Louise aping, you could analyze this for months and still find fresh cringe at every turn. I personally chose the part when Beyonce picks Gaga up at the prison in the ‘pussy wagon’. When the Gagster starts in with that whole ‘Honey bee’ business, I literally vomit in my mouth a little.

“Dancing in the Street” – Mick Jagger and David Bowie
Maximum cringe-osity at 2:49 into the video

It’s pretty well known that back in the day Jagger and Bowie had a little thing with each other, and this video confirmed that the sexual chemistry between the two had not diminished one iota with the passing of time… unfortunately, their COOLNESS had. These two bumble about like two skeletons doing the Halloween shuffle, copping feels off each other like a couple of giggling school boys. Moreover, their drape-y, neon, leopard printed ‘80s finery would make Elton John go….BLECCCHHH! The cringe-iest point comes at the very end however, when they both bend over and shake their bony butts in unison. Ah the ‘80s…that era could lame up the coolest of cats!

“Wake me up before you Go-Go” – Wham!
Maximum cringe-osity at 3:29 into the video

This video is so cringe-tastic that merely watching it instantly turns you into a total douchebag for 45 minutes. The only way to properly view it is to construct one of those pin-hole boxes you use to witness a solar eclipse. George Michael looks like Richard Simmons‘ younger Greek cousin in this thing, as he minces about like a muldoon in his shorty shorts, threatening to expose his tanned butt cheeks to the Universe. It’s practically impossible to isolate one pristine moment of ultimate ridiculousness here, but when they all do the monkey dance at the end, my anus hairs tend to singe from the blue flame of cringe-osity.

“Don’t Cry” – Guns n Roses
Maximum cringe-osity at 3:49 into the video

Axl Rose is an intolerable dipsydoodle, thus, every video Guns n Roses produced has an inherent cringe-y quality to it. This thing however perfectly encapsulates Rose’s untenable cringe-iness into one giant horse pill of cringe-osity. Apparently it was all based on a short story, but I can’t really suss out any semblance of a discernable plot, All I can say is the writer must have been a talentless hack, not to mention a colossal douchenozzle. The highlight for me is the scene where Axl unburdens himself to is shrink (or more accurately, the porn star dressed up like a shrink) and he starts freaking out, making these odd gesticulations. I guess we’re supposed to be witnessing some sort of psychological breakthrough here, but in point of fact, all we’re bearing witness to is a mega-shmuck spazzily preparing an imaginary cobb salad with his hands.

“Rock me Tonite” – Billy Squire
Maximum cringe-osity at 1:31 into the video

Okay, this one really needs no explanation at all. From beginning to end, it’s non-stop cringe. Squire prances around like Ed Grimley on crystal meth, screeching like a capon (that’s a castrated rooster folks). Needless to say, this video completely ruined his career. It’s impossible to understand what his possible motivation was for making this, I can only imagine it was his way of ‘coming out of the closet’ to his fans. It was an admirable intent, but a colossal miss on the execution. I think the crowning cringe blow comes when he tears off his shirt to a freeze frame only to replace it with a pink tank top. I’m telling you the guy was sending a message!!

About Author

I'm a writer/editor with a penchant for saddle shoes, pontification and fried pork rinds. Equal parts gadfly, cut-up, provocateur, philosopher, and silly-willy. My personal heroes include Reggie Jackson, Elvis Costello and Philip Roth.

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