History ThatOneLevel / WideOpenSandbox

[[folder:Grand Theft Auto]]
* ''VideoGame/GrandTheftAutoClassic'':
** Rasta Blasta (the second Vice City level) is notoriously difficult. Not only are the missions noticeably more difficult than the other five missions, you need to amass 5,000,000 points to complete it, the most in the game. It's both a MarathonLevel and CheckpointStarvation eventually kicks in.
** The ''London 1961'' expansion has a lot of its missions as this, because unlike its ''London 1969'' original, you have a lot of missions with strict timers with very little room for error.
* ''VideoGame/GrandTheftAutoIII'':
** "Bomb da Base Act II" is commonly the first mission that's a stopgap. You have to have $100,000 before starting the mission. You have to snipe Colombian Cartel members on a cargo ship to get 8-Ball to blow it up, but thanks to ArtificialStupidity, he sometimes [[LeeroyJenkins rushes in headfirst into Cartel gunfire]], causing an immediate failure. There's an Adrenaline pickup close to where the mission takes place, provided the player remembers where it is. The good thing is that the player [[AntiFrustrationFeatures is you only have to pay the $100,000 once and not on every subsequent mission attempt]].
** "Pay Day for Ray" can be a very hard mission, considering that it is not only a very strict timed mission, but you have to go to several pay phones far from each other around Staunton Island and the game doesn't feature any map to help you with that. The traffic spawns don't help either because sometimes a car can spawn at the wrong time and cause your vehicle to spin out.
** For UsefulNotes/PlayStation2 players, "Waka-Gashira Wipeout!" is a tough mission. First, you must drive a Cartel Cruiser to take out [[spoiler:Kenji Kasen]]. Some of the Yakuza goons have [=M-16s=], who will be more than happy to turn your vehicle into scrap metal. To make this mission even more annoying, you have to be driving the Cartel Cruiser and cannot leave it. While the mission got toned down in later releases, it's still a challenging mission.
** The "Espresso 2 Go" mission requires you to go round the entirety of Liberty City destroying Colombian SPANK dealers posing as coffee sellers under a time limit. It is nearly impossible to hit all the espresso stands in time unless you look for them all first (they show up on the map when you see them, but the timer only starts once you destroy the first one), which is very tiring. In addition, at this point in the game several gangs that own portions of the map with a coffee stand are hostile, most infamously the Mafia in Portland with their shotguns that kill vehicles in two shots, meaning they will shoot at you as you travel through the area - the only upshot is that the game takes some pity on you by deliberately programming them to not use shotguns for this one mission, which would otherwise make it impossible. Even more tedious is finding a good route.
** "S.A.M." is a mission in which you need to take down a plane using a rocket launcher. You have two options to do it, get a boat and take down the plane by the sea (which makes it very hard to aim, considering the distance and speed of the plane) or head straight to the landing strip in the airport, where several heavily armed mooks wait for you. After the plane is destroyed, your wanted level will raise to 4 stars and he will have to go back to the construction site with the heavily armed law enforcement after you. It may get a little easier after you get Ray Machowski's bullet-proof Patriot, but it's still a pretty hard mission.
** In the final mission, "The Exchange", you are stripped of all your weapons and dropped in a courtyard outnumbered and outgunned by Cartel members. Then you have to negotiate the wharf, which is a sniper alley, followed by shooting down a helicopter with a rocket launcher from a long distance away. If the chopper gets away, you start the whole mission over again.
* ''VideoGame/GrandTheftAutoViceCity'':
** The race against Hilary, on so many different levels, it is utterly infuriating. This one little mission has spawned ''countless'' pages of text on Website/GameFAQs explaining every theory and method in this world to beat it. It's ''technically'' optional, but everyone suffers through it anyway because you get $50,000 for the bank robbery, and $10,000 a day for completing the night club asset missions. Money that provides for powerful weapons and a comfortable cushion in the final mission where [[spoiler:Sonny Forelli's men start robbing you blind while you chase after Lance to kill him.]] To give some background, you're setting up a bank heist and you need a good driver. No doubt you are one, but for the purpose of the story it needs to be someone other than you. That someone is Hillary, a very effeminate man with abandonment issues who insists that the only way he'll work for you is if you beat him in a race. Sounds fair, right? Let us count the ways it screws you over.
*** Hilary gets a ''supercharged muscle car''. You get a puny little family sedan. Unfortunately, you don't have a say in the matter. You have to drive the sedan. There is no way in hell you can win a straight race, because your car is in every way inferior. You have to cheat, i.e. knock Hillary off the road, to win. Or just try to keep up with him and hope he crashes into something before you do; sometimes another car will get in his way and cause that to happen, but it's pretty much pure luck.
*** Not two blocks in, the cops get on your tail for street racing. And ''[[GangUpOnTheHuman only your]]'' tail. They don't even see Hillary.
*** Due to game mechanics, you are further punished for getting too far ahead of Hillary. Normal traffic is dynamically spawned 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 has been torn out.
*** And there's a glitch where you might fall ''straight through a bridge'' just before you cross the finish line. This is more likely to happen on the [=PlayStation=] 2 version, due to loading times.
*** The same glitch can happen to ''Hilary'' if you're too far ahead of him, instantly failing the mission.
*** The worst thing about this mission is that it doesn't even make sense. Hillary 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 especially if you can beat him in a much more inferior vehicle. His abandonment issues are no excuse. This guy has effectively locked himself out of his own profession by personally ensuring that he will look incompetent to anyone that hires him.[[note]]Another member of your team, Phil, won't work for you unless you can prove you're a better shot than he is, which doesn't make sense for the same reasons. But his mission is nowhere near as tough as Hilary's.[[/note]]
*** The real insult to that mission is that, despite the effort you go through trying to recruit him, [[spoiler:much like everyone else other than Phil, Hillary ultimately proves to be almost completely useless for the heist. He's there to drive your getaway car. He pulls up in front of the bank in time for your team to get in, but immediately after that he decides to get out and "cover you" by running out towards the SWAT team, who mow him down in seconds. With the getaway driver you worked so hard to recruit dead, you have to make the escape yourself.]]
** But possibly the really most jerk-ass mission in all Vice City is "Death Row". See, you have found that it was [[spoiler: Díaz]] who spoiled the drug transaction upon your arrival at Vice City, so you are quietly drawing closer to him to time the perfect moment to take him out. However, Lance can't stand working for him anymore because he was the one responsible for his brother's death. So he attempts to kill him, fails, is kidnapped and brought to the city's dump to be tortured to death. Right after you are given the mission, a bar appears on the screen indicating Lance's life which is diminishing, and you have to dash to the dumps (note that you start the mission at the very night club mentioned above, and the city's dump is across the other island of Vice City), break through a car barricade blocking the dump's entrance, gun down everyone there to make Lance's escape safe (take into account that the goons are packing submachine guns and automatic rifles, and are even firing from above in the dump's cranes!), and then take him to the Downtown's hospital while sports cars keep pushing and chasing you. While you don't get the money for the mission itself, what's probably the only redeeming part of the mission is that you actually get quite a lot of money from [[spoiler: Diaz]]'s mooks if you kill them. You can make this mission easier by flying a helicopter to get Lance...provided you know where they're parked on the map.
** "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.
** There are two missions with toy helicopters. The first is tolerable, because the helicopter is only slightly awkward in its controls and you're not up against too much resistance. The optional one, a checkpoint race, has controls so damn sensitive that you'd plow into the ground if you so much as ''pressed'' forward. You have to tap the keys as light and as fast as possible just to make controlled movements, and it's ''still'' the most awkward thing in the entire game. Even the full-sized news chopper isn't as bad, and it's the worst of the four helicopters. Mercifully, it doesn't matter if you spend 20 minutes doing it, as long as it gets done.
* "Stunt Boat Challenge", the first mission given by Umberto Robina, is flat out insane. You are required to collect 27 checkpoints strawn across the water canals, but you have to do it under a strict time limit and in a boat that is unforgivingly slow and takes too long to accelerate. While turning the frame limiter on might make the mission easier, it does not always work, and ultimately it all comes down more to luck than actual skill.
* ''VideoGame/GrandTheftAutoSanAndreas'':
** "Flight School". Hours upon hours upon ''god-damned hours'' at failing to pull off perfect barrel rolls and loop-de-loops, and ''it's necessary to continue the game''. The worst part is that flight school starts off deceptively easy. The first two challenges involve simply taking off and landing the plane, respectively, and they're both really easy. But on the third challenge, flight school takes a steep nosedive into the depths of Hell. It's "Circle Airstrip", where you have to take off and fly from corona to corona, all while you're most likely wrestling with the wonky plane controls. It wouldn't be so bad if you didn't have to fly through the damn coronas - which are rather small targets - nigh-perfectly. And when you finish that one, guess what the next challenge is? You have to do the exact same thing, only when you're done you have to land the plane, which is incredibly easy for beginners to screw up. What fun! You CAN make all the flight school challenges a bit easier by just switching to first-person view, but it's still a huge pain in the ass.
*** Oh, and on PC even the first two missions are damn near impossible if you don't have a gamepad, due to the fact that the missions were built around an analog stick.
** And the Flight School missions are easy compared to the driving school missions, notably Burn and Lap.
*** Even Burn and Lap is easy compared to City Slicking. What makes City Slicking so damn difficult, you ask? Having to drive from the driving school to the car showroom across town and back. ''In just two minutes''. Made all the more frustrating by the fact you'll have to dodge endless bouts of traffic on your way there, along with cars making turns at intersections. And that's not all! The car you're using has notoriously bad handling, which means you'll have to slow down a lot before making a turn or you'll fishtail out of control. And if that wasn't bad enough, this mission becomes a goddamn nightmare if you're going for [[HundredPercentCompletion 100% Completion]], because you'll have to make it there and back ''in 1 minute and 40 seconds'', '''''without any damage on your car'''''. Did we mention that you can never stop the car, and that giving in to your instinctive urge to brake when you see you're about to crash into something will count as a failure? Needless to say, this mission will cause a lot of [[RageQuit broken controllers]].
** Zero's first mission was truly frustrating--for a while, it made even the next two seem manageable--in that you stand on a roof, shooting down model bomber planes with a minigun so they don't get a chance to destroy Zero's transmitters. These little buggers ''just keep coming from every single direction'' and worse still, our ''pacifist "friend"'' Zero simply won't stop whining at you. Note that the PC version of Zero's first mission is ''really'' easy, for ironically the opposite reasons as why flight school is so much more difficult (precision aiming with a mouse is simpler).
** And those are cake compared to "Supply Lines". You have to fly an RC plane around San Fierro gunning down five couriers that can spread through out the entire city [[GuideDangIt if you don't know the exact routes they take]] and then land the plane on Zero's store. The catch is you have a ridiculously low amount of fuel to do it with. That mission's actually a lot easier in the post-Hot Coffee editions of the game. The problem with the original is that your fuel acted more as a time meter, i.e. draining even when you weren't accelerating. In later editions, this is fixed so that fuel is consumed only while you're holding the gas button, on top of tripling the amount of fuel you have, making the mission much more manageable (but still by no means easy). Even so, the mission is in itself also pointless. Zero insists that you use his model plane to take out the couriers, and admonishes you for failing at it, when you could have killed all of them in half the time if he just sent you out on foot.
** "Freefall", where you have to act as some sort of air pirate and jump from your plane to another one in order to kill four mafia assassins. It's not just the difficulty of the mission (which mainly comes from how tricky it is to to turn the plane at exactly the right moment at exactly the right altitude; if you don't turn at the right time, you will never catch up to the plane since the plane you're forced to use has inferior speed), but the sheer ridiculousness of not choosing to just gun them down ''after they land'' (even though Salvatore's plan before CJ showed up was to have some of his own men ''do just that''). And also the minutes you spend flying until you get to the place where you intercept the incoming airplane.
** Any mission where you are the driver and the passenger is the shooter, especially if it's on a motorcycle. By and large, they are all terrible shots.
** The two Wu Zi Mu races in a car that has basically no traction on the dirt tracks that make up most of the courses. Unlike Zero's missions, these are not optional and definitely reduce San Andreas' replayability.
** There's two missions from Catalina which qualifies:
*** The first is "Tank Commander", in which you'll have to drive into the red marker outside of the Dillimore gas station to trigger a cutscene. Afterwards, you'll get in the cab with Catalina and back it directly into the trailer to attach it to the cab. Catalina knows of a buyer in Flint County, which is quite a ways away from Dillimore. You have to be very careful when driving the tanker, because too sharp of a turn will detach the trailer which results in a mission failure. The two gas station attendants will pursue you and try to destroy the tanker; the trailer will explode if the health bar the top-right quarter of the screen reaches zero. This can be hilariously easy if you hop out and cap them as soon as you've hitched up the tank, but first-time players may not think to do this because the game tends to vary between "get back to your car or fail" or "fail because you left the car".
*** The other is "Local Liquor Store", primarily because the quadbike you're driving is very difficult to control. In this one, you are tracking down some guys (three of them) who robbed a liquor store, each of the robbers holds a briefcase full of money, so your job on the quadbike is to get Catalina close enough to gun them down. You can use your own SMG if you're carrying one, otherwise you're limited to driving. If the robbers get too far ahead the mission is a failure. You'll have to be especially careful on dirt roads, because if the rancher tips over, it will be nearly impossible to catch up with the bandits.
** "Stowaway". Here's a bike, there's a plane that's taking off ''right now''. Go drive up its loading ramp without being killed by the government agents or hitting a single barrel dropped out the back, because a single mistake equals failure.
** ''Wrong Side Of The Tracks''. You're trying help Smoke gun down some Vagos on top of a train. However, Smoke's aim is very poor, and you'll often find yourself smashed by a train coming the other way. Expect to hear, "All we had to do was follow the damn train, CJ!" a lot.
* ''VideoGame/GrandTheftAutoAdvance''
** "Smackdown" is a tough mission. It's the exact same premise as Kenji's last mission from ''Grand Theft Auto III''. The only difference is that you have a very strict mission timer. It comes down to luck and traffic patterns to complete it.
* ''VideoGame/GrandTheftAutoLibertyCityStories''
** Any of Maria's missions. 90% of the time, the missions consist of [[TheLoad her making you help her buy drugs]], the buyers trying to screw you over in some way, and then you have to chase them down ''on a motorcycle''. Keep in mind, you have to go top speed to keep up with them, which increases the likelihood that you'll crash into some other jackass who comes out of nowhere, which wastes even more time than usual because, again, you have to do so with a ''motorcycle'', and when you crash into something, you are sent flying off of it.
** "The Portland Chainsaw Massacre" will definitely give even the most seasoned GTA veteran trouble. For one, due to the awkward camera perspective that's unique to this mission, you can be blindsided by chainsaw-wielding mobsters. One slice of a chainsaw can easily leave you near critical health, even with full armor and health! If you get surrounded by them, you're dead, no matter what. Your best bet is to gather a lot of Uzi rounds, you're gonna need them.
** "False Idols" requires you to take out three characters who come from different vehicles, one of which is in a helicopter; another drives a bulletproof vehicle. They each have their own destinations, which requires memorization of their routes. You're guaranteed to fail the mission on your first time you play this game.
** "The Shoreside Redemption" requires you to drive to the courthouse with Salvatore Leone in a police van, all while you have enemies ramming your vehicle along the way. Thanks to NoFairCheating, trying to cheat will cause a unique mission failed scenario that's only used in this mission.
* ''VideoGame/GrandTheftAutoViceCityStories''
** Most of the missions actually. "Boomshine Blowout", the ATV race... it's maddening!
** First, let's talk about "High Wire". You're basically pulling an EscortMission with cocaine crates using a huge magnet on the bottom of a helicopter for the first two thirds, and it seems like everything's normal, but then you hear this: "HELP! THE BIKERS ARE ON ME, I CAN'T GET THEM OFF!" and you must go after a moving car that has bikers constantly shooting at it with Sub-Machine Guns, making it move around erratically, in turn causing FakeDifficulty as you're attempting to drive down and collect the car. The [[SarcasmMode BEST PART of this]], you may ask? The car has an HP meter of sorts, and if the bikers hit it enough times(read:about 15 or so streams of bullets), it'll blow up and you'll have to start over from THE VERY BEGINNING OF THE MISSION. Have fun.
** "Jive Drive", which must wholly be blamed on the PSP's lack of a second analog stick. After a hair-raising drive to an abandoned lot, being shot at all the way there (thankfully this isn't terrible as your car has decent armor), you must survive a gauntlet of fire on you and your brother. Lance is useless with a gun and if he dies, WHOOPS, start over. The fact that you can't get a clear look around you with the PSP's limited control scheme is the main reason you will fail this mission
** "Turn on, Tune in, Bug out". You have to destroy 6 police antennas, and with each one you destroy your wanted level goes up and using the Pay'N'Spray trick will only fix your car but ''not'' reduce your wanted level for this mission... that is until ''after'' you destroy all the antenna, which by then you have a nearly maxed out wanted level with the FBI on your tail as you try to get to the nearest spray shop. By the way, reducing your wanted level after the antennas are destroyed is mandatory, or else you fail the mission. And then to top it all off, you get a paltry $300 reward for all the ridiculously hard work.
** "Unfriendly Competition" is a MAJOR DifficultySpike compared to missions before it, it's not too hard until you get to the swimming pool, which is absolutely crawling with enemies and has very little cover, making it insanely hard to kill all the enemies without getting killed yourself, and if you somehow survive you have to chase down and kill the last two guys using a quad-bike, which is very awkward to control and it's hard to drive and aim at the enemies at the same time.
* ''VideoGame/GrandTheftAutoIV''
** The motorcycle chase ones are the worst, because you'll usually fall off your bike from the slightest brush against any obstacle (at which point they'll invariably escape by the time you can get back on.) You will likely break your controller on the mission "I Need Your Clothes, Your Boots, And Your Motorcycle," in which you have to chase and gun down a [[strike:professional stunt cyclist]] mob guy who starts the mission with a block's worth of lead on you, while the game throws every conceivable obstacle at you, up to and including trucks overturning right in front of you.
** 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 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.
** Any of Phil Bell's missions, but Catch the Wave in particular. Having to fight a couple dozen Russian drug runners with automatic weapons in a cramped building with only one entrance is bad enough. The fact that it's also an EscortMission, and Phil happens to be a LeeroyJenkins who frequently gets himself killed is what makes this mission so annoying[[note]]A common strategy is position the truck in a certain way so Phil gets stuck in the door when he gets out, keeping him safe until you clean out the building.[[/note]]. The rest of the mission involves protecting Phil from attacking boats while trying to get to the safe point, and that isn't much easier.
** The Snow Storm. You have to retrieve a package of cocaine from an abandoned hospital while fighting a dozen or so gang members, but the confined spaces make it difficult to aim at the enemies without getting into their line of fire. After you get the cocaine, police special forces (NOOSE) storm the building, and the only way back to the streets is guarded by several police cars. You must push through their lines and escape a three star wanted level (meaning they aggressively ram you, keep shooting your car and have a helicopter). Since the mission takes place on Charge Island, there's only one bridge off, with heavy traffic going out and cops coming in. There ''is'' a lifesaving secret, in the form of a boat at the docks behind the hospital that can be used to easily escape the police, but finding it [[GuideDangIt without a guide is unlikely]].
** Holland Nights. You have to make your way through a project building to get to a target on the roof, all while fighting off enemies. This part isn't that bad if you have good weapons, plenty of ammo and full health and armor on Niko, and they do give you a few health packs throughout the mission. But after finding your target (and either killing him or letting him go), you've got a 2-star wanted rating to shake, and have to escape the building while fighting off cops. And then, you have to lose the wanted rating (which may be even higher, depending on how many cops you killed in your escape) with them still on your tail. And if you die, you have to do the whole long mission again.
** "A Revenger's Tragedy". The mission is full of bottleneck moments. Most notably the part were you have to chase Dimitri's helicopter in a speed boat. Jacob will appear in an Annihilator to pick you up. You have a very limited window to board the Annihilator before Jacob hits the water and the timing can be so finicky at times that some people swear it's glitched.
* ''[[VideoGame/GrandTheftAutoV Grand Theft Auto V]]'':
** "Mr. Philips" - Though redeemed by the fact that you get to play as everyone's favourite badass psychopath, Trevor Philips, for the first time, if you're not sharp on your gunplay, this mission can become a real pain, as it's very easy to get flanked by the Lost M.C. and have your health drained rapidly, even with your special ability activated.
** "Did Somebody Say Yoga?", where a large portion of the level consists of you having to fiddle around with the controls in ''very'' specific combinations in order to perform exercises. And if you fail at any point during a set, you have to do that ''entire'' set all over again. Mess up three times, and you fail the mission. Oh, and the whole time, you have to put up with the annoying chatter of Amanda and Fabien as they comment on your physique. At least the same mission makes up for it somewhat by having [[spoiler:one of the most awesome drug-addled hallucination sequences in video game history.]]
** "The Humane Labs Raid" from ''Online''. ThatOneSidequest on the [[YMMV/GrandTheftAutoV YMMV page]] of the game mentions two of the setups [[note]]"Key Codes" and "Deliver EMP", if you're wondering[[/note]], and the finale is just as bad. You and your crew are split into two teams, and each team has reasonably difficult tasks, but what makes this worse is that both teams are separated from each other and cannot help each other out until about 3/4 into the finale. Coupled with this is a fairly difficult challenge where you and your crew have to complete the finale in exactly 11 minutes, ensuring that [[NoDeathRun nobody gets wasted]] and chopper damage is under 2%. These are what makes this the least popular heist.
*** The ground team has to navigate corridors while the lights are out. Despite the whole facility being pitch black, [[TheComputerIsACheatingBastard the enemy guards have no problem pelting you and your partner with bullets from the first moment they can]]. Normally this wouldn't be so bad except the game pressures you and your partner to hurry to avoid the chopper team from having to put up so much resistance. The game also [[FakeDifficulty reduces the ammo count of assault rifles and pistols to 120 for the duration of the heist]], two weapon types that would be much for useful in the hallways they keep throwing you and your partner into than [=SMGs=] and shotguns, two other weapon types that you will most likely resort to due to you bringing your own ammo.
*** The chopper team has to deal with enemy infantry, trucks, and helicopters outside. The helicopters themselves aren't too bad, but with only one gunner means it can be really difficult to avoid taking a missile to the face due to how long it can take for the pilot and gunner to coordinate an assault on the enemy helicopters. Complicating things is the fact that the chopper team has to focus on both the enemy attack helicopters and try to attack enemies on the ground before they reach the labs and approach the ground team from behind, becoming another factor to hurry the ground team. Finally, you need to hope you have the right players on your heist, because helicopter flying and gunning are both skills a player might not have gotten, while fighting on the ground is mandatory to learn for any player. Also, the game does not make it clear that the gunner can take one of the chaingunners' seats, rather than the front-mounted explosive round cannon, and that it would allow them to switch what side they're on (making coordination much easier), but doing so subjects the gunner to the AI's [[TheComputerIsACheatingBastard pinpoint aim]], making the chaingunner position a liability.
** The Prison Break finale in ''Online'' has absolutely no margin for error, and [[CheckpointStarvation only one checkpoint]] shortly after the beginning: failure means having to start over practically from the start. The players split into three teams, each of which have it rough:
*** The "Prisoner" and "Guard" have to infiltrate the prison and [[EscortMission escort the client]] out of the prison and into the escape plane. The client, thankfully, is [[ArtificialBrilliance smart enough to find cover and stay out of harm's way]], but the players still have to deal with [[EliteMooks NOOSE]] bearing down on them like a wall of bricks.
*** The "Demolitions" player is tasked with stealing a prison bus to run as a decoy while the "Prisoner" and "Guard" team infiltrate the prison. That part is easy: the hard part is protecting the plane the "Pilot" is flying, as well as the escortee once he and two players accompanying him get to a transport truck and start making their way to the airstrip. They are given an armed helicopter to pull this off, but helicopters in this game tend to be very unwieldy: you'll need nerves of steel and a good deal of dexterity to be of any use.
*** The "Pilot" is tasked with bringing the plane to the airstrip for the escortee. Shortly before reaching your destination, however, fighter jets will start coming after you. You can stay mostly safe by staying behind the jets (and if the "Demolitions" player is a decent helicopter pilot, that will make things easier). The tortuous part comes when the escortee, the "Prisoner", and the "Guard" come to the airstrip and it's time to pick them up, all while dealing with a '''five-star wanted level'''. Anything can go wrong here: someone can die, the plane can get shot up, or a stray NOOSE van may clip a wing on takeoff and destroy the plane.
[[/folder]]

** "Bomb da Base Act II" is commonly the first mission that's a stopgap. You have to have $100,000 before starting the mission. You have to snipe Colombian Cartel members on a cargo ship to get 8-Ball to blow it up, but thanks to ArtificialStupidity, he sometimes [[LeeroyJenkins rushes in headfirst into cartel gunfire]], causing an immediate failure. There's an Adrenaline pickup close to where the mission takes place, provided the player remembers where it is. The good thing is that the player [[AntiFrustrationFeatures is you only have to pay the $100,000 once and not on every subsequent mission attempt]].

** In the final mission, "The Exchange", you are stripped of all your weapons and dropped in a courtyard outnumbered and outgunned by Cartel members. Then you have to negotiate the wharf, which is a sniper alley, followed by shooting down a helicopter with a rocket launcher from a long distance away. If the chopper gets away, you start the whole thing over again.

** But possibly the really most jerk-ass mission in all Vice City is "Death Row". See, you have found that it was [[spoiler: Díaz]] who spoiled the drug transaction upon your arrival at Vice City, so you are quietly drawing closer to him to time the perfect moment to take him out. However, Lance can't stand working for him anymore because he was the one responsible for his brother's death. So he attempts to kill him, fails, is kidnapped and brought to the city's dump to be tortured to death. Right after you are given the mission, a bar appears on the screen indicating Lance's life which is diminishing, and you have to dash to the dumps (note that you start the mission at the very night club mentioned above, and the city's dump is across the other island of Vice City), break through a car barricade blocking the dump's entrance, gun down everyone there to make Lance's escape safe (take into account that the goons are packing submachine guns and automatic rifles, and are even firing from above in the dump's cranes!), and then take him to the Downtown's hospital while sports cars keep pushing and chasing you. While you don't get the money for mission itself, what's probably the only redeeming part of the mission is that you actually get quite a lot of money from [[spoiler: Diaz]]'s mooks if you kill them. You can make this mission easier by flying a helicopter to get Lance...provided you know where they're parked on the map.

** "Pay Day for Ray" can be a very hard mission, considering that it is not only a very strict timed mission, but you have to go to several pay phones far from each other around Staunton Island and the game doesn't feature any map to help you with that.

** The "Espresso 2 Go" mission requires you to go round the entirety of Liberty City destroying Colombian SPANK dealers posing as coffee sellers under a time limit. It is nearly impossible to hit all the espresso stands in time unless you look for them all first (they show up on the map when you see them, but the timer only starts once you destroy the first one), which is very tiring. In addition, at this point in the game several gangs that own own portions of the map with a coffee stand are hostile, most infamously the Mafia in Portland, meaning they will shoot at you as you travel through the area - the only upshot is that the game takes some pity on you by deliberately programming them to not use shotguns for this one mission, which would otherwise make it impossible (since shotguns are coded to act like they're firing explosive slugs at vehicles, which is why the Mafia turning on you by this point is so infamous). Even more tedious is finding a good route.

** The race against Hilary, on so many different levels it is utterly infuriating. This one little mission has spawned ''countless'' pages of text on Website/GameFAQs explaining every theory and method in this world to beat it. It's ''technically'' optional, but everyone suffers through it anyway because you get $50,000 for the bank robbery, and $10,000 a day for completing the night club asset missions. Money that provides for powerful weapons and a comfortable cushion in the final mission where [[spoiler:Sonny Forelli's men start robbing you blind while you chase after Lance to kill him.]] To give some background, you're setting up a bank heist and you need a good driver. No doubt you are one, but for the purpose of the story it needs to be someone other than you. That someone is Hillary, a very effeminate man with abandonment issues who insists that the only way he'll work for you is if you beat him in a race. Sounds fair, right? Let us count the ways it screws you over.

*** The worst thing about this mission is that it doesn't even make sense. Hillary 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 especially if you can beat him in a much more inferior vehicle. His abandonment issues are no excuse. This guy has effectively locked himself out of his own profession by personally ensuring that he will look incompetent to anyone that hires him. (Another member of your team, Phil, won't work for you unless you can prove you're a better shot than he is, which doesn't make sense for the same reasons. But his mission is nowhere near as tough as Hilary's.)
*** The real insult to that mission is that, despite the effort you go through trying to recruit him, [[spoiler: Hillary ultimately proves to be almost completely useless for the heist. He's there to drive your getaway car. He pulls up in front of the bank in time for your team to get in, but immediately after that he decides to get out and "cover you" by running out towards the SWAT team, who mow him down in seconds. With the getaway driver you worked so hard to recruit dead, you have to make the escape yourself.]]
** But possibly the really most jerk-ass mission in all Vice City is "Death Row". See, you have found that it was [[spoiler: Díaz]] who spoiled the drug transaction upon your arrival at Vice City, so you are quietly drawing closer to him to time the perfect moment to take him out. However, Lance can't stand working for him anymore because he was the one responsible for his brother's death. So he attempts to kill him, fails, is kidnapped and brought to the city's dump to be tortured to death. Right after you are given the mission, a bar appears on the screen indicating Lance's life which is diminishing, and you have to dash to the dumps (note that you start the mission at the very night club mentioned above, and the city's dump is across the other island of Vice City), break through a car barricade blocking the dump's entrance, gun down everyone there to make Lance's escape safe (take into account that the goons are packing sub-machine guns and automatic rifles, and are even firing from above in the dump's cranes!), and then take him to the Downtown's hospital while sports cars keep pushing and chasing you. While you don't get the money for mission itself, you actually get quite a lot of money from [[spoiler: Diaz]]'s mooks if you kill them. Probably the only redeeming thing from that mission. You would indeed desire to have Lance killed. You can make this mission easier by flying a helicopter to get Lance...provided you know where they're parked on the map.

* Sibrand's assassination in ''VideoGame/AssassinsCreedI''. [[SuperDrowningSkills Insta-death water.]] Jumping from pole to pole over said water with mechanics that don't work very well.
** [[GuideDangIt Go the other way]], through the land strip. You just have to kill a bunch of soldiers and make sure you make the last group of Templars come at you by killing one of them with a throwing knife. After that, when you go for Sibrand, he'll flee ''towards'' you.

** Rescuing Hakuf from Fort Nikiou in ''[[VideoGame/AssassinsCreedOrigins Assassin's Creed Origins]]''. Not only is he right in the middle of the camp, but also the camp is huge and swarming with guards and also two captains and the boss of the area. Also, if you slip up then the guards immediately call for reinforcements which can include a Phylakte showing up (a.k.a a guy who can kill you in two hits at the level you're given it).

** "Pay Day for Ray" can be a very hard mission, considering that it is not only time limited, but you have to go to several pay phones far from each other around Staunton Island and the game doesn't feature any map to help you with that.

*** Hillary gets a ''supercharged muscle car''. You get a puny little family sedan. Unfortunately, you don't have a say in the matter. You have to drive the sedan. There is no way in hell you can win a straight race, because your car is in every way inferior. You have to cheat, i.e. knock Hillary off the road, to win. Or just try to keep up with him and hope he crashes into something before you do; sometimes another car will get in his way and cause that to happen, but it's pretty much pure luck.

** But possibly the really most jerk-ass mission in all Vice City is "Death Row". See, you have found that it was [[spoiler: Díaz]] who spoiled the drug transaction upon your arrival at Vice City, so you are quietly drawing closer to him to time the perfect moment to take him out. However, Lance can't stand working for him anymore because he was the one responsible for his brother's death. So he attempts to kill him, fails, is kidnapped and brought to the city's dump to be tortured to death. Right after you are given the mission, a bar appears on the screen indicating Lance's life which is diminishing, and you have to dash to the dumps (note that you start the mission at the very night club mentioned above, and the city's dump is across the other island of Vice City), break through a car barricade blocking the dump's entrance, gun down everyone there to make Lance's escape safe (take into account that the goons are packing sub-machine guns and automatic rifles, and are even firing from above in the dump's cranes!), and then take him to the Downtown's hospital while sports cars keep pushing and chasing you. While you don't get the money for mission itself, you actually get quite a lot of money from [[spoiler: Diaz]]'s mooks if you kill them. Probably the only redeeming thing from that mission. You would indeed desire to have Lance killed.
*** A helicopter makes this mission easier, since you can park it on a nearby roof then fly Lance to the hospital unchallenged.

** There's two missions from Catalina which qualifies.

** In the final mission, "The Exchange", you are stripped of all your weapons and dropped in a courtyard outnumbered and outgunned by Cartel members. Then you have to negotiate the wharf, which is a sniper alley, followed by shooting down a helicopter with a rocket launcher from a long distance away. If the chopper gets away, you start the whole thing over again.
** The "Espresso 2 Go" mission requires you to go round the entirety of Liberty City destroying Colombian SPANK dealers posing as coffee sellers under a time limit. It is nearly impossible to hit all the espresso stands in time unless you look for them all first (they show up on the map when you see them, but the timer only starts once you destroy the first one), which is very tiring. In addition, at this point in the game several gangs that own own portions of the map with a coffee stand are hostile, most infamously the Mafia in Portland, meaning they will shoot at you as you travel through the area - the only upshot is that the game takes some pity on you by deliberately programming them to not use shotguns for this one mission, which would otherwise make it impossible (since shotguns are coded to act like they're firing explosive slugs at vehicles, which is why the Mafia turning on you by this point is so infamous). Even more tedious is finding a good route.

** "S.A.M." is a mission in which you need to take down a plane using a rocket launcher. You have two options to do it, get a boat and take down the plane by the sea (which makes it very hard to aim, considering the distance and speed of the plane) or head straight to the landing strip in the airport, where several heavily armed mooks wait for you. After the plane is destroyed, your wanted level will raise to 4 stars and he will have to go back to the construction site with the heavily armed law enforcement after you. It may get a little easier after you get Ray Machowski's bullet proof Patriot, but it's still a pretty hard mission.

*** Due to game mechanics, your are further punished for getting too far ahead of Hillary. Normal traffic is dynamically spawned 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 has been torn out.
*** And there's a glitch where you might fall ''straight through a bridge'' just before you cross the finish line.
*** The same glitch can happen to ''Hillary'' if you're too far ahead of him, instantly failing the mission.

** "Unfriendly Competition" is a MAJOR DifficultySpike compared to missions before it, it's not too hard until you get to the swimming pool, which is absolutely crawling with enemies and has very little cover, making it insanely hard to kill all the enemies without getting killed yourself, and if you somehow survive you have to chase down and kill the last two guys using a quad-bike, which is very akward to control and it's hard to drive and aim at the enemies at the same time.

** "Mr. Phillips" - Though redeemed by the fact that you get to play as everyone's favourite badass psychopath, Trevor Phillips, for the first time, if you're not sharp on your gunplay, this mission can become a real pain, as it's very easy to get flanked by the Lost M.C. and have your health drained rapidly, even with your special ability activated.

** [[GuideDangIt Go the other way]], through the land strip. You just have to kill a bunch of soldiers and make sure you make the last group of templars come at you by killing one of them with a throwing knife. After that, when you go for Sibrand, he'll flee ''towards'' you.

** ''VideoGame/AssassinsCreedBrotherhood'' has almost every mission where the Full Synchronisation requirement is no detection or damage. What really makes this annoying is that simply going back to the last checkpoint via death will not reset the Full-Synch requirement back to its fulfillable state - you have to restart the whole bloody memory. And Ubisoft didn't bother fixing this for ''[[VideoGame/AssassinsCreedRevelations Revelations]]'', [[SarcasmMode well done guys!]] But I digress. The part in Sequence Eight where [[spoiler: you need to get to the courtyard in the Basilica di San Pietro within a time limit]] is also very annoying due to its Full-Synch requirement of not killing anyone, combined with the guards getting on your case with abnormal speed.

** Rescuing Hakuf from Fort Nikiou in ''[[VideoGame/AssassinsCreedOrigins Assassin's Creed Origins]]''. Not only is he right in the middle of the camp but also the camp is huge and swarming with guards and also two captains and the boss of the area. Also, if you slip up then the guards immediately call for reinforcements which can include a Phylakte showing up (a.k.a a guy who can kill you in two hits at the level you're given it).
* The final bossfight in ''VideoGame/{{Prototype}}'': Giant monster with tons of health, your normal attacks are useless, the military are constantly shooting and bombing you while you fight, and the only way to get health is to stop and grab a human to eat. Oh yeah, and you're on a timer. Good luck!

** Trying to fill out the Web of Intrigue pits you against the games most nefarious enemy. It is an enemy who has been against you since nearly the first mission. He has made you miserable for many a stage, but with the last few Web Of Intrigue missions, this foe is relentless, cruel, and merciless. This enemy? THE FREAKIN' TIMER!!! You have to cross the city multiple times in less than two minutes to take out the target. Oh, and many of them will be on ground level, in hostile territory, where enemies WILL kill them with you less than an inch away. And even if you get to the final guy at the last second, since it takes you several seconds to "digest" the target unless you manage a stealth kill, then you still can and will fail. Even on easy mode, the time limits are a constant, and it's nearly impossible to pull off these missions even WITH the maximum speed, jump, and glide upgrades. Have fun, tropers! Using the Whipfist and locking on to do long-range grabs will give you a bit more of a cushion, but it's still a matter of luck, and missing once can doom you completely. Even if you get the target on the first try, it's still close.

** "S.A.M." is a mission in which you need to take down a plane using a rocket launcher. You have two options to do it, get a boat and take down the plane by the sea (which makes it very hard to aim, considering the distance and speed of the plane) or head straight to the landing strip in the airport, where several heavily armed mooks wait for you. After the plane is destroyed, your wanted level will raise to 5 stars and he will have to go back to the construction site with the heavily armed law enforcement after you. It may get a little easier after you get Ray Machowski's bullet proof Patriot, but it's still a pretty hard mission.

** The Snow Storm is really annoying, too. You have to fight your way into an abandoned hospital with a dozen or so gang members in it in order to get some cocaine. That isn't all that bad, as you can take cover or flank them with a ladder, but the confined spaces make guessing when you can even hit an enemy and when you can't ridiculous. But that's not the bad part - after you get the cocaine, police special forces (NOOSE) storm the building, so you have to defeat a bunch of elite mooks all on your own (hope you got enough ammo). That, however, is not the worst part, either. After that, you must get out of the only exit while there is a police car with several cops in it coming every few seconds, they practically respawn. You must push through their lines and get to a car, after which you are chased by the police at a three star wanted level (which means, they aggressively ram you, keep shooting your car and have a helicopter) that you must get rid of. It's ANNOYING.
*** One more wrinkle: the mission takes place on Charge Island, so assuming you get to your getaway car, there's only one bridge off, with heavy traffic going out and cops coming in. A traffic jam is highly likely. The saving grace is that once you get off the island, you can usually outrun the cops on the extra-long north-south streets of Algonquin.
*** There ''is'' a lifesaving secret, in the form of a boat at the docks behind the hospital. If you can reach it, the escape part becomes laughably easy.
** "Holland Nights", which is annoying for the exact same reasons "Snow Storm" is. You have to make your way through a project building to get to a target on the roof, all while fighting off enemies. This part isn't that bad if you have good weapons, plenty of ammo and full health and armor on Niko, and they do give you a few health packs throughout the mission. But after finding your target (and either killing him or letting him go), you've got a 2-star wanted rating to shake, and have to escape the building while fighting off cops. And then, you have to lose the wanted rating (which may be even higher, depending on how many cops you killed in your escape) with them still on your tail. And if you die, you have to do the whole long mission again.
*** This mission can be made far easier if, instead of fighting your way through the cops, you jump off the second floor of the building to the streets below, that way you only have to deal with a much more manageable two-star wanted level.

** No Way On The Subway, the mission in which you must chase two motorcyclists through a subway tunnel. Eventually [[NintendoHard they split up]], and don't forget how many trains are coming at you.

** Any of the missions where you need to chase someone in a vehicle and gun them down at the same time. The shooting-while-driving mechanic is well implemented; it's just really hard to track your target effectively while avoiding the obstacles inherent to driving at top speed. And you'll always have to drive at top speed. Complicating this is that half of the missions require you to kill your target while they're still driving and the other half have scripted events where the target gets out of their vehicle and goes on foot (and they're invulnerable until they do this)--and the game usually doesn't give you ''any indication'' of which it's going to be.
** The races 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).

** After completing the "Ruff Rider" mission Weazel News chatter on the radio reports something like 'two men on motorcycles chasing through the streets'. To which the answer was 'Sod that'. Just jack a nearby car, crush the biker under your wheels and chuck a grenade into the mix. Kaboom. Ker-ching'.
** 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 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!
** Any of Phil Bell's missions, but Catch the Wave in particular. Holy shit. Having to fight a couple dozen Russian drug runners with automatic weapons in a cramped building with only one entrance is bad enough...but it's a fucking EscortMission on top of that, and Phil happens to be a LeeroyJenkins who frequently gets himself killed. A common strategy is position the truck in a certain way so Phil gets stuck in the door when he gets out, keeping him safe until you clean out the building.

*** One more wrinkle: the mission takes place on Charge Island, so assuming you get to your getaway car, there's only one bridge off,with heavy traffic going out and cops coming in. A traffic jam is highly likely. The saving grace is that once you get off the island, you can usually outrun the cops on the extra-long north-south streets of Algonquin.

** "Holland Nights", which is annoying for the exact same reasons "Snow Storm" is. You have to make your way through a project building to get to a target on the roof, all while fighting off enemies. This part isn't that bad if you have good weapons, plenty of ammo and full health and armor on Niko, and they do give you a few health packs throughout the mission. But after finding your target (and either killing him or letting him go), guess what? You've got a 2-star wanted rating to shake, and have to escape the building while fighting off cops. And then, you have to lose the wanted rating while those damn pigs just torment you to no end. And if you die, you have to do the whole long mission again.

** Who could forget the mission "A Revenger's Tragedy"? The mission is full of bottleneck moments. Most notably the part were you have to chase Dimitri's helicopter in a speed boat. Jacob will appear in an Annihilator to pick you up. You have a very limited window to board the Annihilator before Jacob hits the water and the timing can be so finicky at times that some people swear it's glitched.

** The final missions (the same one in three parts, actually). To sum up, you have to drive from the power plant to the school carrying a barrel of toxic waste strapped to your bumper which will fall off and explode if you so much as ding a wall with your fender. The path is also extremely unforgiving and the car controls for this game are very sensitive. Did I mention it's a TimedMission? If you lose the barrel, it forces you to run all the way back to the plant. But wait! That's a Timed Mission, too! One that will likely be outright impossible to complete if you've gone even half the required distance, forcing a restart. Oh, and there are certain points where other cars will try to ram you, and if you don't manage to get far enough from them before they turn to chase you, they'll catch up and bump into you, destroying the barrel and starting the above nonsense. The third part also forces you to use a very fast vehicle with sub-par handling, meaning lots of crashes, lots of barrel loss and lots of pain. Finally, because all the above just isn't enough, it's the only mission without a MercyMode.

** The second-to-last mission of Level 6, Set To Kill is very infamous. The player has 1:45 to destroy 15 laser gun stands by ramming them with a vehicle that follow a linear pattern. This is difficult enough, but after doing that, the player is given 50 seconds to drive all the way back to where the mission starts. This requires all shortcuts to be taken and is severely frustrating. What's worse is that most of the time, you'll fail just a second off from reaching the destination.

* ''VideoGame/DontStarve'' is already [[EverythingTryingtoKillYou hard as it is]], but the game ups the ante with Chapter 5 of the Adventure mode, Darkness. You start in area surrounded by [[SuspiciousVideoGameGenerosity campfires, fire pits, and a backpack full of stuff]]. The catch? The chapter is locked on PERMANENT NIGHT, and standing in the dark for more than 5 seconds results in a monster attacking you for [[DarknessEqualsDeath 100 DAMAGE]]. Not only that, but food is painfully scarce, crops won't grow in the dark and your sanity constantly depletes, which will likely result in hallucinations and, subsequently, enemies who can put out campfires and fire pits. The items you need to find to progress are all scattered around the dark. Thankfully, there are several Maxwell Lights around the map to help, but they aren't so useful if you aren't prepared. To make matters worse, this is the last level before the ending of Adventure mode, and dying here will have you restart from chapter 1.

** "S.A.M." is a mission in which Claude need to take down a plane using a rocket launcher. You have two options to do it, get a boat and take down the plane by the sea (which makes it very hard to aim, considering the distance and speed of the plane) or head straight to the landing strip in the airport, where several heavily armed mooks wait for you. After the plane is destroyed, Claude's wanted level will raise to 5 stars and he will have to go back to the construction site with the heavily armed law enforcement NPCs after him. It may get a little easier after you get Ray Machowski's bullet proof Patriot, but it's still a pretty hard mission.

** "S.A.M." is a mission in which Claude need to take down a plane using a rocket launcher. You have two options to do it, get a boat and take down the plane by the sea (which makes it very hard to aim, considering the distance and speed of the plane) or head straight to the landing strip in the airport, where several heavily armed mooks wait for you. After the plane is destroyed, Claude's wanted level will raise a lot and he will have to go back to the construction site with several law enforcement NPCs after him. It may get a little easier after you get Ray Machowski's bullet proof Patriot, but it's still a pretty hard mission.