While browsing my youtube feed this morning, I noticed that this year for Christmas, the AVGN is doing a special series about bad game covers art because well, sometimes it was really fucked up (the Megaman series being a famous one). Like the vlogcembers, there is one new video per day until Christmas:
https://www.youtube.com/user/JamesNintendoNerd/videos

As he will only talk about console games, have you got any examples of some bad covers for PC games (preferably for good games)? Some examples on GOG?

Earlier this year, PCGamer made a short slideshow on the subject.

Of course, there's much, much more to exhume. ^^

I always found the US box art for Carmageddon to be tremendously ugly.
Quite amusing image, though.

I can't think of a really terrible one. Gobliins box art is pretty messed up though:
wat...: http://www.mobygames.com/game/gobliiins/cover-art/gameCoverId,7568/
cheesy smile and crotch grabbing: http://www.mobygames.com/game/dos/gobliiins-1-gobliins-2/cover-art/gameCoverId,47425/

Also, your link to the video series looks broken. :P

Ah, it's the pleasure of having woken up at 3AM, today is gonna be long...... :o)

I think that Jill of the Jungle cover won this thread. :D

This one wins the prize for me.

I mean, Kain is supposed to be a badass, like in this picture, right?

This is definitely one of the biggest discrepancies between game quality and cover quality.

Also, check out this video by LGR.