The Monkees - Pool It! (1987)

Somebody should have told the Monkees that they stopped being teen heartthrobs approximately 20 years before this album got made. Let's face it, there's nothing more depressing than a bunch of doughy, middle-aged men in swimming trunks trying to play like they're still cool. And jesus, what's with the painted-in water? Couldn't they afford to shoot this album cover in a real pool?

Cerys Matthews - Cockahoop (2003)

This album cover proves that no matter how disastrously bad your fashion sense is, you can always make it look that much more ridiculous if you portray yourself with some artwork as drawn by a 10 year old.

Velvett Fogg - Velvett Fogg (1969)

As much as I love bare breasts, and as much as I'm not opposed to the concept of the Summer of Love, this album cover manages to make both seem really unpalatable. Let's face it, any album cover that manages to make bare breasts seem like a terrible thing is committing some serious crimes against nature. And what's with the androgynous cowboy thing in the back? Or that ghostly guy? And what's with the feather boas? This cover is starting to make my head hurt. Curse you, 1960s!

Roger - The Many Facets of Roger (1981)

Among Roger's many facets are his inability to dress himself in clothing that isn't both ridiculous and extremely ugly, his inability to get a decent haircut, and his shameless mugging for the department store camera that undoubtedly was used to create these shots in the first place.

Violet Cohn - More from Violet Cohn

I'm not sure how to read Violet's facial expression here. Either she's been constipated for days and is waiting for her prunes to kick in, or she's completely forgotten that she was supposed to have a photo taken for her album cover and is wondering who in the hell these strange people with cameras are that came into her house and scared her cats. I'm thinking it might be the latter since she apparently took the time to pick out the dress that acted as the best camoflage against her floral print wallpaper.

(as the watermark states, this image also comes courtesy of Bizarre Records)

Christian Crusaders - Christian Crusaders with Al Davis

Given superpowers by the divine love of Jesus Christ, the Christian Crusaders are a crack team of superheroes designed to spread His love across the land! They are:
The Rotund Reverend: He loves Jesus almost as much as he loves food!
Miss Anorexia: She may be wiry, but she has nerves of steel hardened by her faith!
The Midget: A pint-sized soldier in His army, he's still no slouch when it comes to fighting in His name!
Featuring special guest star Emperor Palpatine!

Bay City Rollers - Rock 'n' Roll Love Letter (1976)

Featuring quite possibly the ugliest group of teen heartthrobs ever. Not only do I resent their horrible faces, I also resent that they attempted to do the 80s feathered hair look about four years before the 80s actually began. Their outfits, of course, are too horrible to even mention.

Tony Tee - Time to Get Physical (1988)

I really don't know what's more pathetic here; the fact that Tony clearly needs the two huge guys to hold up his barbell for him (which isn't even that heavy by the looks of it) or the fact that the woman in the weird spandex/technicolor diaper arrangement looks like she's about to kick Tony's ass.If rap is a game designed to make its participants seem as masculine as possible, Tony has lost. Big time.

Mylon LeFevre - Weak at the Knees (1977)

You know, the term "fashion disaster" doesn't seem nearly damning enough in this instance. This guy's outfit is so outrageously bad that it seems like it needs a new term to describe it. Maybe we should start calling extreme cases like this one "fashion holocausts." It's impossible to get too hyperbolic with this outfit, after all.

The Murk Family - Love for All Seasons

Mom had a shitload of floral print fabric on hand and, god damn it, she was going to use it all! I think even the dad's shirt is made out of the stuff. I guess it could've been worse and she could've similarly dressed up the brother (though she might've anyway since I can't get a good look on that shirt of his), horse, and dog, but I think she finally figured out that there's more important things to do after a nuclear holocaust has hit than making sure everybody's clothes match.

The Gospel Tidings - Get Away Satan

These people are so collectively ugly that I'm sure Satan wouldn't want anything to do with them in the first place. "Send these guys to hell? Are you nuts? These people think avocado green actually looks good on them! They're too stupid to be evil! And stop bothering me about tempting the McKeithens. They ain't cutting it either."

Billy May - Cha Cha! (1960)

OK, we get it, it's a fucking cha-cha album. You don't need to put "cha cha" at the end of every single fucking song title. Jesus christ this is almost as bad as any given polka record.

Aside from the irritating name scheme, I'm trying to figure out just what is up with that dress. If you cover her top half she looks like some sort of weird sea creature, one with a love of gold lamé and pink chiffon. This is to say nothing of Ali Balding and his confused ethnicity outfit. The dog is obviously trying to be the black version of Petey from Our Gang and thus looks the least stupid of everybody on this cover.

Sharlene Sharp - Rare and Well-Done

"Hello my dear, nice of you to drop by on my steed tonight. I know the doctors say you're not really there, but I can tell you are! You're just very crudely pasted onto this cover is all, kind of like how I think my horse is. But really, aren't we ALL just shoddy photo-collages in this great big world of ours? My flat pants leg thinks so! Anyway, have some booze, it might help you forget just how loud my suit is."

Y Kant Tori Read - Y Kant Tori Read (1988)

The album that Tori Amos would really like everyone to forget about. Given how horribly 80s her outfit looks on this cover, I think I can see part of the reason why, to say nothing of the 5th-grade level scribbles surrounding her. I'm seriously afraid her hair is going to come alive and eat me, if she doesn't use that cutlass first.

Robbie Basho - The Falconer's Arm I (1967)

Either this album cover features one of the only caucasian Native American asians in existence, or that's the dumbest fucking collection of fashion statements I've ever seen in my life.

Cerrone - Cerrone's Paradise (1976)

My personal paradise also involves nude women giving themselves back problems on ancient appliances and wearing a dorky leisure suit while some mysterious white substance congeals on the floor! It's like Cerrone and I are cut from the same swarthy, hairy cloth!

Vickie Hanson - Vickie Hanson's Aerobic Glow: Fitness in Action

Well the stripes on her shirt certainly make for an interesting optical illusion, until you realize that she's actually wearing those stripes seriously. Then it just becomes ugly.

(The above commentary was provided by my good friend Jeff!)

ABBA - Gracias por la Musica (1980)

This Spanish-language ABBA album poses the question: what is the dorkiest thing about it? Is it:

A) The matching jumpsuits for each couple, as it were.
B) Bjorn's ridiculous facial expression
C) Agnetha and Anni-Frid's mutual ridiculous facial expression
D) Benny's captivating UGG boots
E) The crayon scribbles around the exterior of the photograph
F) write-in

You, the readers, get to choose.

Rusty Warren - Sexplosion (1977)

OH DEAR GOD NO

(Apologies to Retrocrush for co-opting one of their images again.)

Max Bygraves - Viva! Congalongamax Vol. 10 (1975)

That a dorky, middle-aged white guy decided the best way to co-opt/pay tribute to the sounds of Latin America was to wear a hideously gaudy outfit and release a watered down, putrid version of said music is inevitable. That the British public would demand 10 volumes of this sort of thing is just confusing.