The Hardest Missions in the Grand Theft Auto Series

For the most part, the 3D Grand Theft Auto games aren't all that difficult. One of the best parts about the Grand Theft Auto franchise is that most players can easily pick up and play each game in the series without getting turned off by its challenge. But that's not to say that these games don't have their difficulty spikes, because they most certainly do. Anyone who's spent considerable time with the Grand Theft Auto series knows its most notorious and hardest missions by heart — those incredibly difficult and unforgiving segments that have a razor-thin margin for error and are exercises in frustration above all else. The following 10 missions are ones that, for many players, marked the point at which they put down the controller and, in some cases, never returned.

• Game — Grand Theft Auto: San Andreas
• Mission Giver — Mike Toreno

After flirting with aerial vehicles for two games, Grand Theft Auto: San Andreas marked the first point in the franchise at which planes and helicopters became regularly available and a key focal point of many of the game's later missions. But before CJ can enjoy some of the better flight-based challenges in San Andreas, though, he'll first have to pass the incredibly punishing flight school at the heart of the "Learning to Fly" mission. It wouldn't be so bad if the controls for flying a plane were more intuitive, but they aren't, and "Learning to Fly" represents a major stumbling block for most players as a result.

• Game — Grand Theft Auto IV
• Mission Giver — United Liberty Paper Contact

Speaking of challenging flight-based missions, it doesn't get much harder than a helicopter mission where your chances of success depend largely on an NPC ally. Grand Theft Auto IV's "Paper Trail" mission is mostly challenging because you're overly reliant on Little Jacob's shooting ability, which isn't exactly stellar. While you're trying to fly an unwieldy helicopter and keep pace with your targets, Jacob just keeps missing shot after shot, dragging this mission on much longer than it has any business being. Plus, helicopter controls are something that the GTA series never seemed to perfect until GTA V.

• Game — Grand Theft Auto: San Andreas
• Mission Giver — Salvatore Leone

The sheer size and scale of Grand Theft Auto: San Andreas meant that it had substantially more missions than the other PS2-era games, which had the unfortunate side effect of making many of them incredibly difficult. So while both GTA III and Vice City have some hard missions, their one or two difficulty spikes pale in comparison to the regular curveballs that San Andreas throws at players. One of the worst offenders of the bunch is "Freefall", in which CJ has to pilot the slowest plane in the game to try and catch up to its fastest, all while having to rely on the game's RNG and trial-and-error to be successful.

• Game — Grand Theft Auto IV
• Mission Giver — Elizabeta Torres

Sometimes, a hard mission in a Grand Theft Auto game can actually be quite fun, even if it's a little stressful. Such is the case with GTA IV's "The Snow Storm", which is mostly difficult due to the aggressive behavior of the game's law enforcement. Anyone who's played all the GTA games can attest to GTA IV's police being a special kind of vigilant, and that overly-aggressive AI is on full display in "The Snow Storm" as Niko picks up a watched package and has to outrun the cops to pass the mission. Ultimately, if you don't know the different possible escape routes or how to effectively outmaneuver police, "The Snow Storm" is incredibly difficult.

• Game — Grand Theft Auto: San Andreas
• Mission Giver — Zero

It's honestly a toss-up between "Supply Lines..." or "Wrong Side of the Tracks" for being the hardest mission in Grand Theft Auto: San Andreas, but in either case, it's the player who ultimately loses. "Supply Lines" takes the already frustrating controls for flying a plane and enforces a limit on the player in the form of how much fuel the RC plane has, meaning players have to get used to gliding and attacking targets versus using the gas, drawing out an already frustrating mission to the nth degree.

• Game — Grand Theft Auto III
• Mission Giver — Asuka Kasen

The worst part about "Espresso-2-Go" isn't necessarily the mission itself, but the trial-and-error involved in finally passing it. For those who don't remember or are unfamiliar, "Espresso-2-Go" sees Claude tracking down and destroying a total of 9 Cartel-controlled coffee stands spread out across all three of Grand Theft Auto III's islands, but there's no map to use in guiding you. Instead, you have to physically drive by the stands themselves, all while a countdown timer ticks away as soon as you destroy one of the targets. The best way to approach the mission is to drive across all three islands and get the stands to populate the mini-map before you destroy any of them, but even then, it's artificial padding on a mission that's not all that fun to begin with.

• Game — Grand Theft Auto IV
• Mission Giver — Patrick "Packie" McReary

Just like "The Snow Storm", the "Three Leaf Clover" mission in Grand Theft Auto IV is a ton of fun, even if it is incredibly difficult. The difficulty of "Three Leaf Clover" mostly comes into play thanks to the fact that it's long, and failing to complete any part of the mission results in having to start over from scratch. That said, the actual content of the mission is both fun and the inspiration for heists becoming a major part of Grand Theft Auto V (and, seemingly, Grand Theft Auto VI). Thankfully, though, Rockstar has become more gracious with their mid-mission checkpoints thanks to the frustration involved with having to start over "Three Leaf Clover" time and time again for a minor mistake.

• Game — Grand Theft Auto: Vice City
• Mission Giver — Avery Carrington

For the most part, Grand Theft Auto: Vice City is the easiest game in the Grand Theft Auto series (barring Grand Theft Auto V, that is). But there's, of course, an exception to that rule, which mostly comes from the notorious "Demolition Man" mission. Similar to "Espresso-2-Go" in Grand Theft Auto III, "Demolition Man" in Vice City requires players to have some familiarity with each of the targets' locations to beat the timer, which means most of the mission's difficulty boils down to the trial-and-error of playing it multiple times to figure out the optimal route for flying the unwieldy RC helicopter. Thankfully, after this mission, you never have to pilot one of them again.

• Game — Grand Theft Auto III
• Mission Giver — Asuka Kasen

Some of the more egregious missions in Grand Theft Auto III are frustrating specifically because of the runback players have to complete to start them over, and "S.A.M." is probably the worst offender in that regard. Shooting down the plane that's the target in "S.A.M." (which, by the way, stands for "surface-to-air missile) has a razor-thin margin for error that essentially gives players a 50.50 shot of actually completing the mission successfully, and the runback to start over is just annoying. Drive to a pier and hop behind the wheel of GTA III's slowest boat just to fail for the dozenth time? No thanks.

• Game — Grand Theft Auto: San Andreas
• Mission Giver — Melvin "Big Smoke" Harris

Not only is "Wrong Side of the Tracks" arguably the most notorious mission in GTA history, but it also comes so early on in GTA: San Andreas that it's a wonder anyone ever completed the game, given how frustrating it is. One of the more troublesome aspects of "Wrong Side of the Tracks" is that the conditions for failure aren't always clear, and the reliance on an NPC partner to perform the most mission-critical aspects while you simply play wheelman makes it feel like you're never fully in control of passing the mission. A lot of players failed so many times at "Wrong Side of the Tracks" that they simply gave up on San Andreas, which means this one mission cheated them out of one of the all-time great open-world games.