These are the achievments that should have been put in the what were they thinking category.  Here it is, the top five achievments/trophies that are just  frusterating, idiotic, and should not have been put in games.

Riddick: win 1000 matches.  Basic math, let's say the shortest a match can go for is five minutes, game mode, team deathmatch.  5 minutes/match * 1000 matches = 5000 minutes, with a probability of 2:1 of winning the match, if a person is smoking hot, they should clock it in in 5000 minutes, right?  No.

You see, Riddick also has a way of rebalancing teams too, the match goes great, your moping up the other side when suddenly people drop because they hate being pwned.  The game decides that since you were the uber pwner that you should go on the other team to even everything out when your 3/4ths of the way done through the match.  no chance of winning even though the majority of the other teams points came from you.  Right there i just said F*** it and put Riddick on the back burner.

GTAIV: Pidgeons.  200 pidgeons that you have to kill around liberty city, with just a little cash and an achievment to show.  Not as bad as Riddick but i don't want to waste time looking for things unless there is a massive weapon at the end of the sidequest.  I blame Zelda: Orcarina for this, the Gold Skultullas formed the bases of hidden packages, intel, pidgeons, and other find the crap side missions that we find today.

Ninja Gaiden II: Replay game with x weapon.  As much as i love Ryu Hyabusa, i just don't see playing a game over and over with a diferent weapon each time when there are other games i would like to play. 

Multiple Games: The viral tag achievment.  You have seen this one before, kill someone with this achievment to unlock this achievment.  at the begining of a game's life, this achievment is ok, but later, if you don't have it, you haven't played multiplayer yet.

Fable 2 Pub Games: Sync with player in Fable 2, 0 gs.  An achievment... with no points associated... Based on an arcade game where if you got it, chances are you would be getting Fable 2 anyways...  This is the anti-riddick here, where there is no work and no reward.

What I would like to say is Achievments and Trophies should be based on mostly skill and not wasting time.  Sides, who want's to win more than 1000 matches in any game other than CoD4.  On the other hand, make the achievments mean something too.  There is a fine line between skill and monotony.

Now, if you excuse me, I need to play some Contra. 

-NOTE-
Most of these achievments are on an xbox 360 perspective since i do not own a PS3. 

-EDIT-
Looks like i'm not the only person upset with the pidgeons in GTAIV, strongschwarts also has a similar rant on his blog, here's the link
http://www.giantbomb.com/profile/strongschwartz/achievement-unlocked-nothing-else-nothing-else/30-26852/