The Grand Theft Auto series is chock-full of memorable missions. After all, developer Rockstar needs to fill its massive open worlds with things to do, and one of the best ways to introduce more content is through new missions. Unfortunately, some of these missions really seem to have it in for the players. They’re nearly impossible to beat your first time through, and a few of them will give even veteran fans fits.
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Here are the five hardest missions in Grand Theft Auto‘s long history.
5) The Driver – Grand Theft Auto: Vice City

One of Grand Theft Auto‘s most important mechanics is carjacking. It is, after all, in the name. That also means you get to drive around some pretty sweet rides that you don’t have to pay for. I’m not saying I’d steal a Ferrari off the street in real life if I could get away with it, but you have to admit it’d be pretty fun.
Because GTA games are so car-centric, Rockstar often includes racing missions. Generally, these aren’t too bad because you get to use a souped-up racer to blow past the competition. Not in Vice City. During The Driver, you have to beat expert racer Hilary King in a race. He gets to use a powerful muscle car, and you’re stuck with your mom’s four-door sedan. Oh, and the cops start trying to ram you off the road halfway through because you’re engaging in an illegal street race.
4) Wrong Side of the Tracks – Grand Theft Auto: San Andreas

This San Andreas mission is iconic, but for all the wrong reasons. During Wrong Side of the Tracks, you hop on a motorcycle with your good pal Big Smoke and have to chase down a train filled with Vagos gang members. As you rip through the city and countryside, Smoke will try to shoot the gangsters.
Unfortunately, today appears to be the first time Big Smoke has ever picked up a gun. The guy couldn’t be a worse shot, and he acts like it’s your fault when you inevitably fail. The 20th time you hear him wail, “All we had to do was follow the damn train, CJ,” you’ll want to take that gun and show Smoke how to shoot. Unlike a few missions on this list, this one is required, so you’ll need to practice those motorcycle skills.
3) Espresso-2-Go! – Grand Theft Auto 3

If you know what you’re doing, this one is much less difficult. Don’t get me wrong, it’s still a challenge, but when you learn the spawn points for the espresso stands you need to knock off, you have much more of a chance. See, this mission forces you to quickly race around Liberty City and take out nine espresso stands. You have seven minutes and fifty seconds to complete your goal, so learning the perfect route is key.
However, that’s not the only part of the battle. You will also be shot at when you reach a new stand. That means you need to keep your car intact while speeding through the city and dodging bullets. It’s not easy by any means, though guides showing you the path (and telling you to get the Patriot car from the Marked Man mission first) have made it a bit simpler.
2) Demolition Man – Grand Theft Auto: Vice City

One mission chain missing from this list is the Pilot’s License test in GTA: San Andreas. Those missions are required to complete the game, and teach you all about how terribly San Andreas‘ control scheme maps to the air. It’s a slog, but because it’s a series of missions and not a one-off, I didn’t include it here.
Thankfully, Demolition Man is here to pick up this stinky crown. This mission puts you into an RC copter, which might control worse than the real thing, especially when you consider Rockstar had another game to “perfect” the controls between this and the pilot test. You need to plant several bombs around a construction site while workers try to shoot you down. Worst of all, there are no checkpoints, so if you fail, you’ll have to start over from the top.
1) Supply Lines – Grand Theft Auto: San Andreas

The good news for Demolition Man is that it is not the worst mission in the series. That’s reserved for Supply Lines, which is an optional mission in San Andreas. You have to help out your good friend Zero using, what else, an RC plane.
This time, you have to take out moving targets with your plane that handles like it’s moving through jelly. Once the mission starts, your five targets will begin moving. You have limited fuel, so you have to perfect the art of gliding to make sure you can make it to each target and back to base. Doing this without a guide has broken many who have tried. The only saving grace is that it isn’t required to complete the story, but if you want that sweet 100% on your save file, you’ll have to survive this ludicrous challenge.
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