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F*ckin' sanity effects...
Watching the Mario 3 warpless record yesterday, thought of how maddening it must be when a hand pulls you down in the last world...so close to the end. Another contender for me is the Grunty questions near the end of a Banjo-Kazooie run.

What's the most blood-boiling, controller-snapping, break-your-fist-when-you-punch-the-wall RNG ever?
Thread title:  
Waldo subway.
Mega Man X7, midboss that can waste ~40 seconds, a boss that can go far away from you, another boss that can do attack which is behind the fight area, and much more
Edit history:
I have no name: 2016-02-12 02:14:52 pm
I have no name: 2016-02-12 02:14:26 pm
Obscure games ftw

(skip to 52:40ish, the forum isn't letting me link to a time)

This takes the cake for me. The final boss of Ape Escape can only be damaged after one of his 4 attacks, and takes 4 hits. He won't use the same attack twice in a row but if the attack requires a destroyed arm, then you can get multiple arm lasers in a row. From this, 5 attacks is optimal.

After the best run I'll likely ever have, I got 28 attacks and lost 2 minutes.
Get over here!
Risk of Rain is a pure RNG fest.

Broforce with all Bros which has a completely dumb RNG script to screw you over on purpose (they have a tier list for the bros and you're more likely to get useless ones before the god tier).

The Ship: Murder Party starting RNG i.e. if you don't get remote detonated purse you can reset.
Intruding N313 and F014
Anything that is a coin flip, where getting the bad RNG costs a significant amount of time.  NES Metal Gear has plenty of those, especially the guard that captures Solid Snake because there are 2 of them in a row, and the bad RNG for each costs 3.2 seconds.
may use a few too many Kappas
Pokemon Puzzle League's S-Hard mode is a sub-20-minute run through 16 stages of gameplay if done really well at a really high level. However, even mistake-free play can result in MULTIPLE MINUTES of time loss through seemingly no fault of your own because the opponent has the right combination of colors of blocks to clear all of the garbage you send. Remember, the colors of the blocks on each stage are RNG and not reasonable to manipulate in real time. This can happen on EVERY SINGLE STAGE. It is not uncommon for even the top runners to have trouble finishing a run in under 40 minutes.
NowOwnsAFreaking Plane
Quote from CardsOfTheHeart:
Pokemon Puzzle League's S-Hard mode is a sub-20-minute run through 16 stages of gameplay if done really well at a really high level. However, even mistake-free play can result in MULTIPLE MINUTES of time loss through seemingly no fault of your own because the opponent has the right combination of colors of blocks to clear all of the garbage you send. Remember, the colors of the blocks on each stage are RNG and not reasonable to manipulate in real time. This can happen on EVERY SINGLE STAGE. It is not uncommon for even the top runners to have trouble finishing a run in under 40 minutes.

This whole thing so much.  Speedrunning puzzle games are terrible for RNG in general (I mean, it's totally different every singe run), but out of all the puzzle games, PPL really takes the cake.
Borderlands 2 Glitch Hunter/ router.
Borderlands 2 from start to finish 2:20:00~ of pure RNG, Bioshock Infinite HRH, Rainbow Six Vegas 1 and 2 - not so much RNG as such but the AI are so ... Brutal that you will be killed if the game wants you dead and when some missions are 15 - 20 minutes long that can really fuck you off in a big way.
The worst rng I've encountered so far has been Ikari Warriors for the nes. The character is slow-moving and the fire power has limitations, so a lot of possible enemy spawns/movements are undodgeable.

You also need to rely on lucky drops twice. Without the drops, the attempt is invariably over. The first is at around half-way into the run (total run time ~30 min). The drop rate there is ~50%. I played nothing else than this game for more than 6 months and arrived at this point 20 or so times. That included a streak of 8 or 9 times in a row without the drop. That was pretty discouraging. The same drop is needed a few minutes before the end. The drop rate there is something like 10-20%. I've been there twice on proper attempts, but didn't get the drop. I'm currently finishing up something else, but will then prepare myself for another 6 months (or more) of Ikari warriors until I manage to brute-force the needed drops...
0-10
http://www.hitbox.tv/video/890341

The whole game is RNG. Sad While you can work your way to mitigate the RNG, it is still very strong and determines everything.
In Final Fantasy XII, you do a farm for levels and money a little over an hour into the game that lasts about 20 minutes and is very boring.  About 15 minutes later you get to find out if you got enough money.  There's a good chance you will be too poor.

Later there's a boss that can block your magic.  If he blocks enough, you have to scramble to finish the fight.  The very next boss is five enemies that have mostly random movement patterns.  You want to get them all in a group to hit them with a move that requires step manipulation, and they don't always group up nicely enough for that.  Then, any you missed can hit you with tons of status effects.  The boss after that is also very trolly, in that it can hit you with several bad status effects, and/or just off characters.

Later on, there's a boss and summon duo that has a chance to just off your tank with their basic attacks with a critical shot and/or combo respectively.  If that happens, the rest of the fight is a mad scramble to not die.

The final boss block also has several things that can troll you harder than you might expect.  Most of these are fairly subtle, though and I've already said a fair bit here.  And I didn't even talk about Order of Ambrosia (100%)...
Edit history:
Efreeti: 2016-02-23 12:44:01 pm
Clear as a crisp spring morning!
On behalf of UltraJMan, allow me to nominate that damned lizardman that needs to walk in front of that damned light in the Confusion Gate area in La-Mulana's original version. He can literally jump around and climb wrong ladders for minutes, it's entirely random when he actually goes where he needs to go. I believe the remake fixed this slightly.
Castlevania (NES), stage 4 axe drop which is basically a coin flip and destroys WR pace runs. Stage 5 random drops can also screw you.
Edit history:
NewGamePlus: 2016-02-28 04:23:01 pm
NewGamePlus: 2016-02-28 04:22:31 pm
Su-Pah-Hu-Man! (#2-Run Refuser)
Quote from Uilnslcoap:
Watching the Mario 3 warpless record yesterday, thought of how maddening it must be when a hand pulls you down in the last world...so close to the end.


I don't think I've ever played that spot in SMB3 and NOT gotten pulled down by at least one hand.  If one hand doesn't pull me, I get a little giddy inside, and if 2 don't, it's a good day.  One always does though.  It's like one of the additional things that are certain in life... "Death, taxes, and that at least one hand will pull you down in SMB3".

In general, the worst for any run would be

(1) completely random things not determined by anything else BUT randomness
(2) that are
    (a) not foreseeable, and/or
    (b) that you can't do anything about
(3) that come at the end of runs after you've potentially pulled of many rare and difficult feats already

There's something like these for nearly every game, but in my most recent experience, I'd have to say mine would be with my most recent full-season stunt of NHL 99 (N64) where either my guys randomly get up on offense in the zone and don't get back enough (and when they do do this, they will tend to play an entire game with the same problem throughout, so it's like they've conversed in the locker room or something to decide which games they're going to screw me over), or when on defense when I switch to them after an opponent gets the puck, their first move will be to FLY RIGHT BY the puck carrier often just peeling off COMPLETELY THE F AWAY in the OPPOSITE F-ING DIRECTION for no reason at all.

And then, there are what I call "stat rating goals" where a guy will take a shot from either center ice, or approaching the blue line, or even I've seen from between THEIR blue line and the center red line, and just dump or shoot it in, and my goalie goes into a reaction graphic that puts the pads down in a wide open manner, sweeps the stick across in front, and lets it right through the 5-hole.

When it happens from a superstar like a Paul Kariya or any Detroit Red Wing (for that matter), I call it a "stat rating goal" because the only reason they got the goal was because the star players often have like 13-15 of 15 for their shooting categories, and so even if the shot sucks, the computer just says "Ok, that player's rating is high enough, so sometimes it's just going to go in nomatter what".  But when it's someone like 2nd line defenseman "#38 V. Malakhov" on the last place Montreal Canadiens, then it's no longer about the rating and the computer is just randomly letting them have it.

Worst case in this stunt is when you go the whole game with your Jennings Trophy candidate goalie (least goals allowed in minimum 25 games played) and you manage to play such a tight defense all game long to where the opponent gets NO shots on net the whole game... and then the ONE shot you allow is the one that makes it in... and it's like that... that's the most infuriating by far.

The whole idea of the stunt, btw, is to play a full 82 game season plus playoffs winning every end of season award (but not necessarily every single game), in ONE full 2-day long marathon session, and the hardest ones to get are the Byng and the Jennings.  So even though it's not absolute perfection since you have a considerable margin of error, the RNG-caused blunders all kind of "add up" over the duration.  Penalties behind the play are almost entirely RNG and they instantly destroy a players candidacy for the Byng since absolute 0 on PIM is a requirement UNLESS you're leading the league in points with a player who has like 2 minutes, and the next best person with 0 is really super duper far behind on the leaderboard.