I was thinking about what kind of achievement related column I could do often. I have been playing Top Spin 2 now for over 14 days for a single achievement, so Achievement Hell was the first thing that popped into my head. Achievement Hell columns will contain my frustrations with a single achievement in a single game, though sometimes I might branch out and do more than one achievement from that game for the column. This week will contain 2 achievements from Top Spin 2.

Reach #1 World Rank in career 100
Reach the top of the World Rankings while playing Career Mode to receive this achievement.

End career with 1 000 points 250
Finish an entire career and score more than 1 000 career points to receive this achievement.
The thing that makes Top Spin 2 horrible is that it is a very quick game to get the full 1000 achievement points in if you don't suck at it. If you do suck, it is an agonizing hell of attempting to sim matches in Career and having to go back to the dashboard to re-sim it when you lose because of the autosave feature that you can't turn off. YAY! for forced autosaves. It is very unlikely that you can sim a win against the computers that are in the top 10 and damn near impossible against the ones in the top 3. The #1 in the World achievement becomes a game of not actually beating your opponents but trying to make sure you do better than the top players so you advance above them.
As I said, the #1 achievement is do-able with time because you don't have to win the tournaments. So with a solid week, you can get 750 points out of 1000 for this game. The kicker achievement is the 1000 Career points. For this achievement, you actually have to win tournaments! Oh noes! When I ended my Career the first time, I had only 842 out of the 1000 needed. Luckily I had a back-up save, and I am now currently reworking my way through the last of the 5 seasons. If I don't have the 1000 points after this season, I am going to have to create a new character and start all over again and at that point I think a bullet into the brainpan (squish) is a good idea.
Achievement Hell - That 10k achievement in GoW. Serious.. I think its called.
yea. That is a rough one, especially when I get like 2 kills a 30 minute match.
I just blasted the hell out of Need For Speed Most Wanted to get all 1000.... but it was Mass Effect that consumed my life. I ended up beating the whole game roughly 6 times to get evry last point.
Look, I love going for achievements probably a lot more than I should - hell, I participated in dvddesign's achievement contest from January through June. However, shouldn't you make sure the achievements you're going for are actually fun? Hell, shouldn't the game be fun? I can't see the point in torturing yourself like this.
That being said, if you're looking for crazy achievements to go for, try getting Transmissionary in Dead Rising. What's annoying is that you can go for the Saint achievement (save all 50 people), get that, and still not get Transmissionary because you missed one inconsequential call. Trying another run where you don't save anyone and only take the calls doesn't work either, since you have to save a certain number of people to get calls about refugee disputes later in the game.
The achievements in Sonic the Hedgehog 360 are also quite bad, considering how much they make you master a bad game.
If you're looking for something crazy to do though, try getting some of the achievements in Yaris. I've documented my struggles with that game, and let me say, it will destroy you as a person. Good luck if you go for all 200 like I did.