Trophies and Achievements that are seriously silly or extremely and almost impossible.

[Drops a Sweet Katana]

I find mulitplayer achievements to be a particular pain in my ass, the Overkill and Two for One achievements in Halo 3 in particular. The act of getting an Overkill medal or killing two people with one shot from a Spartan Laser in most gamemodes isn't too difficult or frustrating, but when you have to do it in a ranked free-for-all lobby (a 6 player lobby), shit gets ridiculous. Overkill requires that you kill everyone bar one within 4 seconds of each other. What makes this a right ass is that you will rarely have all players concentrated enough to be able to this outside of a KotH match, and when you do, chances are they'll kill each other before you can kill enough for an Overkill. Two for One is easily the worst. You have the same sort of problem as Overkill in that you'll rarely find the right concentration of enemies to be able to pull it off, but add to that the Spartan Laser's 3 second charge time AND having to line to enemies up while they are most likely fighting. In that 3 seconds, you'll either be killed or one of your targets will kill the other. Add to this the fact that the SL can only be found on 1 FFA map and you've got an achievement that requires more luck (or cheating) than skill to achieve, thereby defeating the whole point of achievements.

 

[chaser5000]

Sly Cooper: Thieves in Time
Sparrow Approves: Use the compass many times to navigate.

Except... "many times" means 500 times. This does NOT include the automatic compasses that appear with each new objective. And being a veteran Sly 2 player, I'm far more accustomed to looking through my Binocucom to find my objective, should I ever need a refresher.

I cannot fathom what Sanzaru was thinking when crafting this Trophy. The game isn't very long, and its audience, surely, is mostly fans of the games. Nobody playing it is going to be so bad or so forgetful that they'd use the compass 500 times in a single playthrough.

Kingdom Hearts: Re:Chain of Memories HD
Moogle Mogul: Get over 10,000 Moogle Points.
Regular Customer: Use over 20,000 Moogle Points at Moogle Shops.
Expert Deck Builder: Edit a deck 500 times.
Card Master Sora:Collect all Card Collection entries in Jiminy's Journal.

Moogle Mogul requires one to be holding 10K MP at once. This meant that I had to forego Moogle Shops for the entire first playthrough, and then grind Moogle Points (a random overworld drop) to reach 10K. Your average playthrough just plain won't hit that number naturally. So obviously you'll see the problem with Regular Customer as well.

Card Master Sora is effectively 100%ing the game. But this includes enemy cards, which are a an incredibly rare drop. For reference's sake, I would grind through enemies for around three hours at a time, and get maybe one or two enemy cards in that time. And this was in the rooms which increased the drop rate.

And as for Expert Deck Builder... well.
There's also the problem that in Kingdom Hearts HD 1.5 ReMIX, difficulty Trophies don't stack. Meaning I needed to play Kingdom Hearts Final Mix three times for Platinum, and will need to play through Re:CoM six times in total (three playthroughs for Sora and Riku each).

Feel your pain man, I've taken a break from going after the platinum for final mix for now just need to do all the gummi missions and do two more play throughs and after I read about needing six play throughs for chain of memories i just said fuck that.

 

[AusGamer44]

The Little Rocket Man achievement in Half Life 2 Episode 2.
You have to cart around a little ceramic garden gnome FOR THE ENTIRE GAME and then stick him in a rocket at the end and close the door and send him into orbit. Seriously,I don't know how anyone could have the patience to get it to stay in the car or park it somewhere when fighting off hunters or other beasties. Although one guy did,and made a pretty amusing walkthrough for it.
http://www.pentadact.com/2007-10-15-gnome-quest/
Another guy even wrote a blog AS THE GNOME with screenshots. Just hilarious.
http://treygnome.blogspot.com.au/

 

[AusGamer44]

The unachievable achievement from The Stanley Parable. The achievement description is literally "It is impossible to get this achievement." Really, all of the achievements in that game are rather silly, such as the one where you don't play the Stanley Parable for five years, or another one where you play The Stanley Parable for the entirety of a Tuesday.

I actually got that achievement. I have no idea how,though.