That One Level/Boss

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Xaldin can actually be cheesed with reflect magic. As far as nasty bosses go "The Binding of Isaac" may as well be that one boss the game. Along with The Bloat which was mentioned above here's some of the more cheap bosses you can encounter:

Pink Haunt: Has a brimstone laser that bounces off of walls.

Dingle and Dangle: Have a multi-charge that is very fast and has an uncanny homing ability which can catch you off guard. They also spawn minions.

Peep: Basically the kinder, gentler version of The Bloat which isn't saying much. The creep it spews out and the eyes are a major pain to deal with.

Brownie: This thing spawns massive amounts of minions including cluster bomb piles and turns into a Dangle when its health gets low enough.

Hush: First off, before you even fight the true boss you have to fight another boss with a number of annoying attacks. This thing is basically the Isaac equivalent of a Touhou boss with complex bullet patterns some of which you have very little chance of dodging unless you get lucky, very fast eye beams that follow you everywhere, it can spawn clusters of minions, has huge amounts of health, and finally it can crouch into the ground where it becomes invincible.

Mega Satan: Has two forms with the first having several stages between which it summons other bosses that you have to kill. It will summon all of the four horsemen, the super versions of the sin minibosses, and the two angels. It also has some insane shockwave and bullet patterns.

Gurdy Jr: This piece of crap has a very fast bouncing charge that it pretty much does not telegraph. It can also spawn minions and bullets and the game loves to stick you in small rooms with it.

They actually "fixed" the Lost in the Afterbirth expansion, but you have to go through Greed Mode to do it. If you donate 879 coins to the Greed donation machine the Lost will always start with the Holy Mantle. As far as Hush's continuum tears are concerned the problem is you have no idea where they are going to start raining down from so you can easily get hit when they first start.

Actually there are a number of ways to really cheese the Keeper. Swallowed Penny and Wooden Nickel being two of the most obvious ones. The Lost also has spectral tears now so that makes cheesing with him more doable plus they added more items that synergize well with Gnawed Leaf like Succubus.

Chapter 19 Map
Game: Fire Emblem Fates Birthright [and there are those who say that this game isn't hard on Hard Mode...]
Reason: Normally, my best characters [Ryoma, Takumi, Setsuna, and Kaden] can defeat most enemies with little effort, but not on this map. Even Ryoma, my ace, can barely bring enemy units down to half health, when before he could easily solo entire maps. Argh! I still haven't beaten this map...

Boss:Yukiko's Shadow
Game: Shin Megami Tensei Persona 4
Reason: Chie has quite a weakness to Fire in this fight so keeping her alive is rather difficult.

Boss: Leena's Father
Game: Chrono Cross
Reason: Leena's Father is basically death incarnate without casting Diminish

Boss: Commander Deko, Stage 7
Game: Sin and Punishment: Star Successor
Reason: Bullet hell! I probably died 100 times to him, not exaggerating.

Boss: Megaman Battle Network 3
Game: Megaman Battle Network 3
Reason: Every boss in this game is hard, except Flashman who is a pushover. First three that come to mind are FlameMan and his torches, BeastMan, and BubbleMan and his annoying screen-filling projectiles.

Chapter 27 Map
Game: Fire Emblem Fates: Birthright
Reason: There's enemies surrounding you with powerful weapons, and as such most of your army are fragile speedsters and can barely even do scratch damage, and the final boss has half damage from everything, and he [unlike other bosses] can move and attack you.

Turok Evolution - Every Pterodactyl flying chapter. Those controls, man. I just made it to chapter 3 for the first time. I had cheats on, but fall damage and crashing into stuff can still kill you and inf. ammo does not work on Pterodactyl missiles.

Serious Sam - Ugh-Zan III - I HATE this guy.

Serious Sam 3 - Ugh-Zan IV - As if III wasn't bad enough. Just like III, I got through the game without cheating until I met this guy.

Serious sam 2 - Kleerofski - He starts off invincible and what you have to do to make him vulnerable is really annoying and tedious if you're not fast enough.

Destroy All Humans! 2 - Every Natalya escort mission. Some aren't so bad, but there's one in Tunguska, where she has lower health than usual.

Borderlands - Crawmerax - I'm almost finished with the General Knoxx DLC and I'm not looking forward to fighting this guy anytime soon.

Mass Effect 2: The Suicide Mission. Although I managed to get through the first time without a hitch and all squad mates surviving, it was nerve-wracking.

God of War games. Not bosses fights, but certain traps and obstacles that proved so frustrating to get around. So much that I don't want to play anymore

Mass Effect 2: Archangel Dossier mission, especially the Blood Pack segment. For a mission from the beginning of the game, it is hard and can be frustrating.

That bloody perpetually upper cutting wrestler jerk off in Streets of Rage 2, his rhythm is hard to get down, man is he a fountain of fury!

In tales of symphonia where that surly redhead Kratos turned on me I pretty much spent about fifteen minutes surviving until I succumbed and found out I was meant to get steamrolled by him for the sake of the story lol.

The whole of Silver Surfer, I find it excruciating to complete a single level!

The final battle in Bioshock Infinite.

Wesker in Resident Evil 5.

Azazel in Tekken 6's Arcade mode.

Ornstein and Smough.
Sans.

OKAY I've freaking got some:

Mario Maker, the "official" level set (not the 10-mario challenge ones), ANY of the Bowser levels. Any of them.

I'll just put it this way: the next time someone I know starts going on about how Nintendo ONLY ever makes "casual" stuff, I'm going to sit them down in front of that, and force them to play those until they either A: beat one of them, or B: start crying blood. Either way, they wont say that too much anymore.