Well, a few games to list:
Painkiller - try getting all those secrets, I ended up screaming in rage so hard, it was actually something similar to the Pantera song "The Great Southern Trendkill".
Super Meat Boy - this game magically couldn't piss me off like, at all. I could only complete the Kid's warp zone in 3 hours (that's a clusterfucking 1 hour per screen...) and it felt so glorious when I completed it that I was emotionally moved. However, when a friend asked me to complete that christmas achievement (Golden Gift - complete "The kid's christmas in one go"), it kinda killed me. Not only couldn't I finish it despite already having it at home, the fucking PC crashed on the last level. I've got it in 15 minutes on my next try though.
Beating Seth with Dhalsim in Street Fighter 4 - NNNNNNNNNNNOooooooooooooooooooooooooo. That slow twat can expand all he wants, he's still a miserable piece of slow crap against the hyper-speedy last boss. Fuck it.
Limbo - it's meh. I've got all the achievement (wasn't easy) only to not get the 100% game icon on my XBLA profile. Shite.
Trials HD - just try and get that last level. If you got it, I hate you cause I'll never be able to do it.
The Binding of Isaac - it's one of the few games I'm fairly good at. I only played 60 hours, and have all achievements except for 2. Golden God (all items, missing only 2 at the moment) and Dark Boy (complete the Depths without getting hit). I mean, I got the womb alright, but the depths seemed to be freaking impossible. Then I reached Mom without getting hit, only to get trolled by her stupid hand that reaches out from a door when I was hiding from one of her spammed critters. She was down to like 5 or 6 hits.
And my winner is....
Need For Speed: High Stakes. Just that game in itself. It has overly long and timewasting races with usually 8 laps to speak of (8 VERY, VEEEERRRRYY long laps, mind you), and then there's the fact that you have to constantly repair your car for money, which costs so much that you'll end up wasting all your hard-earned bucks on the same car without being able to buy a better one. Oh, but there's always the easier levels where you can grind on, right? Yeah, they're equally as hard and they'll eat up your money anyway, as you'll keep crashing your car; your very hard to control car. It's a neverending circle, and I believe it doesn't matter how skilled or pro you are at it, you only need some luck to proceed. Sometime I got totally broke and had no money and a few wasted cars to race with, so when I fired up an early level to get some money, I kept losing so hard, I ended up punching my keyboard which resulted in some buttons flying out of it. It was totally like some clerk flippin' out at mildly stupid costumers, after having to deal with the same type for years. NEVER play this game if you are easily angered. Never. I warned you.
HONORABLE MENTION: Aladdin in Nasira's Revenge.
The game's alright for a movie tie-in, but then there's that snowy-slidey part in that one particular dungeon... Disney's only fix for that level was a way to get past it without trying, as it was so hard that only a few people were actually able to finish it. Me? challengeaccepted.jpg (SPOILER: it's fucking impossible)