History ThatOneLevel / GrandTheftAuto

* "Bar Brawl". Right after you [[spoiler:off Diaz and become the new boss]], you have to go to the mall to smash store windows. The clock is set to five minutes... starting from your mansion! For reference, the mall is at the north end of the first island, and you start from the center island. A good driver with a fast car (which the house will provide) can get there within 1-2 minutes, leaving three minutes to kill everything in sight, but if you get bogged down you fail. There's a helicopter on the roof that can get you there even faster, but there's a chance that won't spawn, forcing some SaveScumming to get it.

* 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.

* "Cop Land", where you dress up as cops and set up explosives at the mall. You can only drive to the mission in a cop car, [[ThisIsGonnaSuck with all other traffic in the area also being cop cars]], and RIGHT after you set the explosives off, and despite wearing cop uniforms you IMMEDIATELY gain a five star wanted level and everyone zeroes in on you, somehow. Since you presumably don't have a regular car and the Pay 'N' Spray won't take a cop car, the point of the mission is to get back to the mansion from the other side of the island with a near full wanted level and survive. It's incredibly tough to do even in a fast, tough cop car. Did we mention this mission is only at the halfway point of the story mode? Adding to the frustration is that you need to keep Lance from getting killed, and he's relatively easy for the cops to kill. If all you needed to do was get ''yourself'' to safety, it would be significantly easier. There exists a resprayable Vice Cheetah somewhere parked somewhere in the PC versions onward, but if you don't know where it is or if you're playing on the [=PS2=] original, you're out of luck.

* Right after you [[spoiler:off Diaz and become the new boss]], you have to go to the mall to smash store windows. The clock is set to five minutes... starting from your house! For reference, the mall is at the north end of the first island, and you start from the center island. A good driver with a fast car (which the house will provide) can get there within 1-2 minutes, leaving three minutes to kill everything in sight, but if you get bogged down you fail. There's a helicopter on the roof that can get you there even faster, but there's a chance that won't spawn, forcing some SaveScumming to get it.

* "Stunt Boat Challenge" and ""Checkpoint Charlie", both boat driving missions where you have to drive through a set number of checkpoints under a rather unforgiving time limit. The boat itself has pretty bad controls, with sensitive steering, slidey handling, and pitiful acceleration.

* The race against Hilary is an utterly infuriating case of TheComputerIsACheatingBastard. 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.]]
* "Death Row", which is easily the most hated mission next to racing Hilary. To explain, you now know that Díaz is the one that messed up your deal at the beginning of the game. Tommy is content to wait it out, but Lance, like an idiot, [[LeeroyJenkins jumps the gun and gets himself captured]]. You have to rescue him before he's beaten to death. You have to do this starting at the Malibu, while Lance is being held at the dump on the other side of the map. His remaining health [[TimedMission is your timer]], and starts right away. Sounds annoying yet? Good, because [[FromBadToWorse it gets worse]]. The dump is barricaded by mooks armed with automatic rifles and high-powered machine guns which will chew through even an armored Tommy or a helicopter if you do a flyover. They're positioned high up on cover to make killing them harder and more time-consuming. Once you rescue Lance, you have to get him to the hospital, which is when three sports cars with goons decide to chase you down. If you blow them up, a fourth comes along. It also respawns (albeit slowly). On top of ''all of that'', there's literally no reward. You don't get paid jack for one of the hardest missions in the game. Perhaps to make up for it, Díaz's mooks drop the largest amount of lootable money, the next mission gives you the most powerful assault rifle in the game, and is practically a cakewalk unless you're criminally incompetent thanks to not only Díaz's guards less frequent at his mansion, but [[ArtificialStupidity they often fail to notice you if you're far enough away, and tend to have trouble navigating certain pathways to get to you]]. If you know where a helicopter is parked, it becomes a bit more manageable.
* Right after you [[spoiler:off Diaz and become the new boss]], you have to go to the mall to smash store windows. The clock is set to five minutes... starting from your house! For reference, the mall is at the back end of the first island, and you start from the center island. A good driver with a fast car (which the house will provide) can get there within 1-2 minutes, leaving three minutes to kill everything in sight, but if you get bogged down you fail. There's a helicopter on the roof that can get you there even faster, but there's a chance that won't spawn, forcing some SaveScumming to get it.
* "Cop Land", where you dress up as cops and set up explosives at the mall. You can only drive to the mission in a cop car, [[ThisIsGonnaSuck with all other traffic in the area also being cop cars]], and RIGHT after you set the explosives off, and despite wearing cop uniforms you IMMEDIATELY gain a five star wanted level and everyone zeroes in on you, somehow. Since you presumably don't have a regular car and the Pay 'N' Spray won't take a cop car, the point of the mission is to get back to the mansion from the other side of the island with a near full wanted level and survive. It's incredibly tough to do even in a fast, tough cop car. Did we mention this mission is only at the halfway point of the story mode? Adding to the frustration is that you need to keep Lance from getting killed, and he's relatively easy for the cops to kill. If all you needed to do was get ''yourself'' to safety, it would be significantly easier. There exists a resprayable Vice Cheetah somewhere parked somewhere in the PC versions onward, but if you don't know where it is or if you're playing on the [=PS2=] original, you'll have to have hoped one is in your safe house garages.
* Love Juice. You start at the [=VRock=] HQ and have to head to a nearby location to meet a drug dealer. Upon meeting him, he then takes your money without giving you the product and runs, while a cutscene lets him escape on an incredibly fast PCJ-600 bike, while the game expects you to chase him down. If you aren't aware this is going to happen, you might not even be facing the right way, and you have about five seconds to follow him before the game declares the misison a failure. Once you take out the dealer, you get a call telling you to go and pick up Mercedes from her apartment to bring her to the gig before the band start playing. Once you pick her up, the game gives you an absurdly strict timer of only 1 minute and 20 seconds to get to the gig location. If you fail it (which you will if you don't know what's coming next), you do it all again. Chase down the dealer, pick up Mercedes, and drive like crazy to make it on time.
* "Stunt Boat Challenge", the first mission given by Umberto Robina, is flat out insane. You are required to collect 27 checkpoints strewn 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.

* "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.

* The finale mission definitely qualifies, not because it's difficult (as you'd expect it to be) but because regardless with option you take, the mission is extremely long, with no opportunity to save and no checkpoints. Both versions involve a very long car chase, then an intense gun battle, then a chase in the water or in the air, and then finally a footchase. Not to mention, during your first time of this finale, it's easy so mess up during the chase if you don't know the scripted sequences or signs of them.

* "Freefall" can be frustrating beyond all comprehension, mostly due to the fact that you're screwed by the interface from the start. The short version is that you have to kill a jet full of targets by jumping to it from a ''Dodo''. The jet won't arrive until you find it up north, beyond the borders of map. This means you only get a second or two or warning when you do finally find it, which takes a while. Then you have to do a 180 degree turn without screwing up so you can fly through a ring just above its tail while going the same general direction. Your Dodo can barely outrun the jet, and that's if you have the advantage of being higher than it. You'll never catch it if you have to climb. This you have to do while struggling with very frustrating controls. Oh, and you have less than a minute to manage all this, because the jet counts as landed if it gets over the city. ''Then'' you have to kill all the bad guys on the plane, while forced into a first-person target mode that only lets you duck behind cover, and you can only use a pistol which takes several headshots just to waste one of them. This is one of those missions where cheating through various means may actually be preferable to doing it fairly, given how difficult it can be to pull off. The best part is that it's ''delightfully ridiculous''. If the widely-touted "something new in every mission" pre-release prospect showed itself rather questioningly in any one mission, this would probably be it.

* There's two missions from Catalina which qualifies:
** The first is "Tanker 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".

* "Bomb da Base Act II" is commonly the first mission that's a stopgap to even veterans of the series. 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]].

* "Silence the Sneak" has a lot of FakeDifficulty in the [[ScrappyMechanic maligned grenade throwing system]] since it requires you to throw a grenade in a precise spot which is several stories above ground. It is even harder to accomplish on mobile devices. Aside from potentially forcing the player to waste a lot of grenades just to blow up the damn window, it can be very easy to get killed by the splash damage. And then there come the target himself (who is in a pretty fast Sentinel) and his two bodyguards which carry AK-47's. Oh, and you get a three star wanted level too, which means that many cop cars will try to obstruct you from completing the mission.

* "Escort Service" has you guard the Old Oriental Gentleman's armoured truck as it makes its way to Shoreside Vale from Staunton Island. Sounds easy, right? You and the van will get harassed by the Cartel cruisers, though they are the least of your problems. The true nightmare is the gunmen which are placed in such a way you will not be able to reach them with your Uzi before they attack, and they shoot very precisely, whittling the truck's health points down in no time at all. It also does not help that the truck takes a long detour through the underground tunnel, and the Colombians won't stop pursuing you even there.
* 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. While part of the mission is in Saint Mark's, the Mafia only uses Uzis for this mission, making it a bit less difficult. Even more tedious is finding a good route because you will inevitably run out of time if you chose the wrong route after hitting a coffee stand.

* 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.

* "Grand Theft Auto" would be a pretty easy mission if it weren't for one thing. At this point in the game, you have [[spoiler:assassinated Salvatore]] and earned the ire of the Mafia. One of the vehicles you are tasked to steal is a Mafia Sentinel, which can only be found on Mafia turf, turf that is now crawling with shotgun-wielding wise guys that can waste you in seconds. You better hope that you have a Mafia Sentinel saved in your Portland garage.

* The race against Hilary, on so many different levels, it an utterly infuriating case of TheComputerIsACheatingBastard. 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.

* Portland as a whole becomes flat out dangerous after you beat the Staunton Island missions. Out of the three gangs that reside there, [[spoiler:all of them turn on you at one point or another, including the infamous Mafia goons with shotguns that hit like a truck. Mafia mobsters in particular occupy the area north of where the hospital and the police station are]].

* 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 Portland Chainsaw Massacre" will definitely give even the most seasoned GTA veterans 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.

* ''Wrong Side Of The Tracks''. You're trying help Smoke gun down some Vagos on top of a train. The problem is that [[GuideDangIt there isn't an indication]] that you need to stay at least another train's width apart from the train or Smoke can't hit them. Furthermore, you'll often find yourself smashed by a train coming the other way. The mission is rather trivial once you figure out the correct way of doing it but expect to hear "All we had to do was follow the damn train, CJ!" a lot until then.

* ''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.

** 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.

You'll be wishing you have followed the damn train once you get through these tough ''VideoGame/GrandTheftAuto'' missions.

* "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.

[[folder:The Lost and Damned and The Ballad of Gay Tony]]

[[folder: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]]

* 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 because getting GameOver means you have to redo the entire level from the beginning.

* "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.

[[folder:Grand Theft Auto IV and Episodes from Liberty City]]

* 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.

* "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 because you will inevitably run out of time if you choose the wrong route.

* 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.

* "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.

* 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.

* 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.

[[folder:Grand Theft Auto Liberty City Stories]]

[[folder:Grand Theft Auto Vice City Stories]]

* The ATV race can easily be a source of frustration due to the Quad's tendency to fishtail. If it's raining, you might as well forget the race.
* "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.

** 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.

* "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.

* "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.

[[folder:Grand Theft Auto IV]]

''VideoGame/GrandTheftAutoV'' has enough of these to have [[ThatOneLevel/GrandTheftAutoV its own page]].

[[folder:Grand Theft Auto (Classic), London 1969 and 1961]]
* 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.

* "Bomb da Base Act II" is commonly the first mission that's a stopgap to even veterans. 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]].

[[folder:Grand Theft Auto (Classic)]]

* 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.

* "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]].

* 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.

[[/folder]]