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[TempAcc]

Here's a low hanging fruit I think nobody mentioned so far:

Spoiler (click to show/hide)

Ah yes, night trap, that one game in which you have to save some people from conspicious robot ninja zombies by controlling cameras and activating traps, and that was controversial for no reason because the helicopter parent media interpreted one really tame scene involving a girl being kidnapped while she was getting ready for a shower as a "rape scene".

The box art depicts the game's antagonistic family as vampires and a half naked girl going "wtf" at all this, justifiably so.

Additionaly, for a more recent example:

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The worst depiction of sumo wrestling I've ever seen outside of the realm of porn. The fact that this is apparently based on a cartoon series makes it all the more disturbing.

Spoiler (click to show/hide)

Ok, elemental master doesnt look THAT bad, but its still pretty hard to take it seriously since it involves some cheap stage magician making an odd dramatic pose as massive ghostly hands try to grope him out of existence.

[spoiler]
WEREWOLVES WITH METAL HORNS FOR CLAWS FOR NO REASON. You'd think this is some cheesy altered beast knockoff from this cover art, and it probably is.

Spoiler (click to show/hide)

Yes, this is Mario, the Mario, facing old style Donkey Kong with mjolnir and the power of his mullet.

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I'm not sure if this is bad or just way too cool for me to apreciate. Platinum abs will always be a most ambigous sight.

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I always loved Stallone, but he could've at least tried to look a bit more enthusiastic about this whole dramatic cliffhanger thing.

A blast from the past for me:

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I played this during my youth. Its a pretty bad game overall, but it had some interesting ideas. Plot wise, its rather interesting, since it follows the plot of a certain setting in one of the many universes of Magic: The Gathering. Whats baffling is that, despite the actual game having some pretty great art and MTG being know for its awesome card art, the best cover art they managed to come up with was a barely plot relevant minotaur wizard with super furry legs about to smite you with a spell.

But truly, none can compare to this:

Spoiler (click to show/hide)

I'm... Actualy pretty baffled at this one. Its so bad that I think it crossed the threshold from so bad its good to its actualy pretty bad after all. It holds so many mysteries though. Why is one of the half naked barbarians stepped on a cat's tail? What is oozing out of the other guy's horn? Why is barbarian guy holding his axe like that? So many mysteries in only one image.

[Neonivek]

I am sad to say but...

Super Duper Sumo box art... Freakishly enough was probably the best you were going to get.

It makes more sense if you know the show. So it falls under "Good Cover art of a terrible thing"

I'm not sure if this is bad or just way too cool for me to apreciate

It is bad, but what you have to do to know it is bad is look at how the head is positioned compared to the rest of the body. Seriously just TRY to do the same pose as that Platinum cyborg.

It is actually incredibly difficult. What with the bow legs, leaning forward puffed up chest with his right side slightly leaned back... and his Head just completely straight.

Honestly a cookie to anyone who does the Turrigan pose.

[Bouchart]

The PS1 version of X-Com could've used some work.  It looks more like Attack of the 50 Foot Sectoid.

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[Mech#4]

It does show actual things from the game but the composition is a bit off.

Hey... there's that alien navigator again. You don't see that in game except on the "Alien Navigation" research topic. The one on the right, blue with the cybernetic eye thingy.

I'd like to see the full picture of that blue back artwork, there's what looks like a Snakeman in the middle right, just above the coloured picture.

[wobbly]

Spoiler (click to show/hide)

I always loved Stallone, but he could've at least tried to look a bit more enthusiastic about this whole dramatic cliffhanger thing.

Pretty sure Stallone is actually afraid of heights, so may be his real expression there...

[Bouchart]

I'm really not a big fan of Stonekeep's box art either.

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If they did away with that off-center skeleton in the pickelhaube and just made the whole cover that blackish stone texture it would have worked better.

[That Wolf]

But truly, none can compare to this:

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I'm... Actualy pretty baffled at this one. Its so bad that I think it crossed the threshold from so bad its good to its actualy pretty bad after all. It holds so many mysteries though. Why is one of the half naked barbarians stepped on a cat's tail? What is oozing out of the other guy's horn? Why is barbarian guy holding his axe like that? So many mysteries in only one image.

Oh wow a guy standing on a cats tail. A massive slab with blood n guts (secrets of life and death) written on it. A drinking horn. Multiracial cast. Axes held inapropriatly, partial nudity
Oh armok all its missing is dwarves!

Just look at the cats expression, classic

[MonkeyHead]

I found some more.

Spoiler: Super Duper Sumos (click to show/hide)

... yeah, they are rubbing butts.

Spoiler: Final Fight (click to show/hide)

Now, kiss.

Spoiler: Bill Laimbeers Combat Basketball (click to show/hide)

Nothing says "futuresport" like chrome body armour.

Spoiler: Dinocity (click to show/hide)

1992 called. It wants its dinosaur back.

Spoiler: Bomberman (click to show/hide)

Look at those cold, dead eyes. LOOK AT THEM!

Spoiler: Streetfighter 2010 (click to show/hide)

Its the future. You can tell because chrome armour.

Spoiler: Megaman 2 (click to show/hide)

Somehow worse than its predecessor. More chrome armour, too.

Spoiler: Ghost Lion (click to show/hide)

80's workout attire, swords, boots, and a lion. Epic combo.

Spoiler: Kid Kool (click to show/hide)

Floating castle island, green dog thing, brown shoulder bird, bubble hurling giant semi invisible wizard, and 80s fashion. What's not to love?

BONUS EDIT!

Spoiler:  The Great Giana Sisters (click to show/hide)

This is wrong in so many ways. So, so many ways.

Spoiler: E-SWAT (click to show/hide)

Chrome armour = future, again.

Spoiler: TransBot (click to show/hide)

All Master System box art is horrible. But this is more horrible than most.

[Levi]

I remember playing Dino Eggs as a kid. 

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Also Jumpman was the shit.

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Not all C64 games had bad art though.  Telengard's box was awesome.

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In game it was a little less awesome.

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[Bohandas]

Spoiler: Aaarghhh! (click to show/hide)

Satan wrestling a dragon. Nuff said.

For some reason to me it looks more like they're about to have rough sex.

[Neonivek]

Its the future. You can tell because chrome armour

If you played the game... That guy actually does wear that in the game.

Also it is a bad game.

[motorbitch]

hu, whats wrong with  that giana sisters cover?
call me nuts , but i think its kind of cool.

[Nick K]

Yeah, the Great Giana Sisters definitely have better nipples than the Super Mario Brothers, so it makes sense to put them right there centre-stage in the box art.

[birdy51]

I owned Combat Basketball once upon a time. It was actually kind of fun.

[Tawa]

Spoiler (click to show/hide)

It's immature of me, but I giggled when I noticed that it looked like you were "Ass Level 1".