History ThatOneLevel / WideOpenSandbox

** The ambulance optional mission is also ridiculously difficult. You have to collect all 78 patients necessary for the infinite run unlock in one go. You cannot fail after so many patients and build up to a total, as you can with the fire truck, police car or taxi optional missions. The ambulance is also one of the crappiest vehicles in the game: it handles like a brick, can take very little damage, and tips if you so much as turn a corner at half-speed. Accidentally running over any patient forces you to restart, and the cops refuse to give you even this much free reign--ding a cop car and you are still fair game, humanitarian mission or not. Sure, it is optional, but that infinite run is very, ''very'' useful, even if you are not after HundredPercentCompletion. Expect to spend lots of time on it.

** "All we had to do was follow the damn train, CJ!"

** The ambulance optional mission is also ridiculously difficult for forcing you to collect all the 78 patients needed to get the infinite run in one go. You cannot fail after so many patients and build up to a total, as you can with the fire truck, police car or taxi optional missions. The ambulance also handles and takes damage quite poorly, accidentally running over any patient forces you to restart, and the cops refuse to give you even this much free reign--ding a cop car and you are still fair game, humanitarian mission or not. Sure, it is optional, but that infinite run is very useful, even if you are not after HundredPercentCompletion. Expect to spend lots of time on it.

** Any of the missions where you were forced to chase someone on a motorcycle, ''especially'' "I Need Your Clothes, Your Boots, and Your Motorcycle." You're chasing a guy down on a motorcycle, and due to the mechanics, if you're going more than about 15 miles an hour, and so much as ''bump'' into anything while on a motorcycle, Niko goes flying 50 feet, and you have to go back and get back on the bike, meanwhile your target is jetting away at 60 miles an hour, avoiding every traffic obstacle with superhuman skill. Did we mention that during this chase, the game throws literally every obstacle in the book at you? There's random explosions that go off in your path, absurdly narrow tunnels and alleyways, an ''18 wheeler that flips over and spills stuff everywhere'', random car crashes, and an incredibly long underground tunnel that you've got to navigate. And unlike some chase missions, where you've simply got to keep up with him for a while, after which he goes off on foot, where you can easily gun him down, you've got to kill him on the bike, using the crappy targeting system, all while trying to keep up with him, and not get thrown off your bike and lose him.

*** Optional? If you don't beat Hilary, you can't unlock the final mission.

*** Pffh. Even on the PS2, those levels had migraine inducing controls. It's a wonder that ''anyone'' completed those levels without wanting to break the game disc. You think the developers learned from their misfire, and decided NOT to create MORE annoying and [[NintendoHard ungodly difficult]] flying missions for San Andreas...[[WallBanger NOPE]].

** SaintsRow one has several, but the two that stand out are the last missions for Los Carnales and the Vice Kings. In the Carnales mission you and Dex have to drive to the airport and kill their leader before he escapes in his plane. Sounds straightforward right? Well, one you arrive you'll notice two things. One, there are about 20 mooks with rocket launchers that can kill you in about three hits. Two, your vehicle is on a set path. This means that unless you am perfectly you'll get blown away before you can even get close to the plane. Even better, you'll have about two or three cars shooting up your ass as you try to avoid geting blow away by the RPG's. The cherry on top? YOU HAVE TO RESTART FROM THE BEGINNING OF THE MISSION AND WASTE TWO MINUTES DRIVING BACK TO THE AIRPORT EVERY. TIME. YOU. DIE. But that's just the first mission. The Vice King's mission? You have to drive King's car (it HAS to be King's car, no switching out if it gets too damaged) to Impressions and interrogate Stefan by driving while King holds him outside the window. The whole time more and more police show up to clusterfuck you into a corner where they will blow your car up and force you to start over. But wait! The mission isn't over after you interrogate Stefan, oh no. You then have to store the Vice King stronghold. If you die during the fight? Back to the very start for you! Have fun listening to Stefan whine for the 5th time. Thankfully, SaintsRow 2 has checkpoints in missions.

* Ohhhhhh, the race against Hilary in ''[[GrandTheftAutoViceCity Grand Theft Auto: Vice City]]''. ''Imagine racing against a supercharged muscle car with a puny little family sedan, with the cops on your tail.'' This one little mission has spawned ''countless'' pages of text on {{GameFAQs}} explaining every theory and method in this world to beat it.
** Not to mention the fact that the police only pursue you and leave Hillary alone. Even worse, the game inadvertently punishes you for getting too far behind or too far ahead of Hillary, because your main obstacle, traffic, only appears within 100 meters or so of your car. If the distance between your car and Hillary's is great enough, you get bogged down in traffic while he has a clear road with no such obstacles, either allowing him to catch up (if he's behind you) or get yet further ahead (if he's in front of you). Either way, much hair was torn out.

** 'Checkpoint Charlie' from the same game. A checkpoint race where you need every single second to do the course... and you have to do it in a boat, which means that you can never predict how you'll come off of a wave, or how you'll land after a jump. Not something you'd ever want to do again.
** The worst thing about this mission is that it doesn't even make sense. Hilary is supposed to be the best driver around, that's why you want him. So why would you have to race him first? If he only works for people that can beat him, he's obviously NOT the best driver. If you hire a plumber, you also don't have to prove to him that you're better at plumbing than he is, because if you were, you wouldn't need him.
*** The whole point of that mission was to show Hillary he could trust you and that you would not leave him. He has abandonment issues according to one of the characters.
*** The real insult to that mission is that, despite the effort you go through trying to recruit him,[[spoiler: Hilary ultimately proves to be completely useless for the Heist. He's there to drive your getaway car, but all he ends up doing is getting shot and killed, so you have to make the escape yourself.]]

** The races in ''GrandTheftAutoIV'' were pretty awful too, especially "No. 1" since you couldn't cheat your way out of it (calling Brucie to cancel a race before crossing the yellow arrow yourself guarantees you first place).
** I'm not sure how how entirely fair calling the Sentinel a puny little sedan is, but I don't get why he got a Sabre GT. I mean, if he was going to be using a taxi, he should have raced with it! And the fact you have to drive there and [[spoiler: and he has to kill himself]] are some of the lowest points of the game. But, what can you expect from an optional mission in a 2003 game.
* ''GrandTheftAutoIII'' has a mission in which you're given the crappiest, slowest, worst handling car in the entire game and told to go to another island and shoot up dozens of members of an enemy faction. Anyone who's ever played a ''GTA'' game can tell you it's hard to even '''get to your destination''' without wrecking the car you're currently driving; now imagine having to get there, deal with a good amount of armed gang members and get back to where you started, all with a car that's ridiculously easy to flip over (flipping over a car in ''GTA'' irretrievably destroys it) and with the police relentlessly chasing you all the time. Oh, did I mention you cannot under any circumstance leave the car? And to top it all off, when (not if) you wreck the car, the goon that's traveling with you is revealed to be its owner, and he and his pal get pissed and proceed to shoot you full of holes.
** The ambulance optional mission is also ridiculously difficult for forcing you to collect all the 78 patients needed to get the infinite run in one go. You cannot fail after so many patients and build up to a total, as you can with the fire truck, police car or taxi optional missions. The ambulance also handles and takes damage quite poorly, accidentally running over any patient forces you to restart, and the cops refuse to give you even this much free reign--ding a cop car and you are still fair game, humanitarian mission or not. Sure, it is optional, but that infinite run is very useful, even if you are not after HundredPercentCompletion. Expect to spend lots of time on it.

** Speaking of Ruff Rider, the mission right after that, Undress to Kill, can be extremely annoying for beginners, especially if you don't know tricks like knifing the first strip club manager. Not to mention it's possible to, as happened to ThisTroper, get a GameBreakingBug where Playboy won't open up the next mandatory mission, The Holland Play, after completing Undress to Kill, making the story unwinnable. Fun!

* The final mission on ''Driver: Parallel Lines'' It's pretty reasonable until you have to chase down Corrigan, first you have a strict time limit to escape from a tunnel after Corrigan blows it up, not only do you go very fast while narrowly avoiding falling debris, but seemingly every single car is actively trying to drive right into your path to slow you down. Then you have to chase after and shoot down Corrigan's helicopter, which isn't a problem if you have plenty of SMG ammo(it also helps if you max RPG ammo, but it's pretty tricky to time it just right so that the rockets hit him) but the heavy traffic can really slow you down, and you'll fail if you take too long to catch up, and later on Corrigan flies over areas with lots of bumps and hills where it's real easy to accidentally flip your car over and fail the mission, so you basically have to fire RPGs and SMGs at him nonstop, hoping that you'll get lucky and be able to finish him off quickly before he flies over the rough terrain areas.

----
<<|ThatOneLevel|>>

* All of the Oblivion gates from ''TheElderScrollsFour''. They're filled with junk, hard to navigate, and populated by some of the most annoying enemies in the game. The best way to deal with these is to ignore everything until the very end and grab the one useful item that ends the level.
** "Filled with junk"? In addition to the expensive loot carried by the legions of Daedra you fight (especially the 800 coin rings carried by the Dremora), the final room contains 2-3 leveled treasure chests carrying a vast amount of money and enchanted equipment.