Nice list. I don't think "Working the Land" from Red Faction is that bad though. The flags from Assassin's Creed 1 are far worse. :P

I highly approve of this list.  It's a really nice concept and I'd love to see more added.  Maybe some people will give you some more suggestions.
 
Ditto about the AC1 flags btw.  I mean I never really tried for that achievement, but then there was a very good reason that that never even entered my mind as a realistic possibility.

Add Halo 3's 7 on 7.

Seriously? Working the Land? If anything, Revolutionary is the most difficult achievement in Red Faction: Guerrilla. I had to play through the game to completion three times before getting the achievement.

You need to include one of the laughably easy achievements from the Ultimate Mega Drive Collection. Like beating the first level of Shinobi III without using a continue- a normal player can do it without getting hit yet alone without losing a bunch of lives first.

 
That outrageous number of zombie kills in Dead Rising was pretty ridiculous too. 
 
EDIT: Also, The Simpsons Game with its easiest achievement ever deserves a nod.  Come to think of it, that's one of the few achievements from that game I actually bothered with.  Hm.

Batman: AA  Freeflow Perfection,  that drove me to the brink of insanity. Borderlands has 2 good ones, the Mario-esque style one were you have you to jump on something to kill them or the Sucka Born Every Minute in which you spend a ton of money...for NOTHING!? Or the legendary Bejeweled 2 in which you have to play Endless mode for about 400 hours for 10 gamerscore

Quake 4 (Xbox 360) must be on this list, for the same reason GRAW is. Check it out!

What about that Alan Wake achievement  for viewing an in-game advert?  http://bit.ly/d4dmFE

I got all the Agility Orbs in Crackdown without a guide and had fun doing it.

I am proud to say that I collected all agility orbs without any help.

 Going to suggest adding the achievement for getting all the tech orbs in Enslaved to this. There are hundreds of the fucking things scattered around, many of them intentionally hidden. Getting every single orb in every chapter is a ridiculous thing to ask a player to do. I have some chapters where I've collected 99% of the orbs and the idea of going back in looking for the 1 or 2 I missed is cringe-inducing.     

What about the old GTA series? 
G-G-G-GARUNGA!!!

Got at least 5 of these, for better or for worse.

The Red Dead Redemption achievement is one of the best.