If nothing else, the Grand Theft Auto series is known for its wild assortment of dangerous missions. In the case of Grand Theft Auto: Vice City, which has a total of 87 missions, some of the most difficult involve vehicular tasks that prove nearly impossible to defeat in the first attempt due to the clunky controls of the cars, trucks, bikes and boats.

In addition to the automotive challenges, Vice City also presents some of the hardest shootouts, bomb missions, and solo objectives in the entire GTA universe. As Vice City nears its 20th anniversary, it’s only right to revisit some of the game’s biggest hurdles.

10 G-Spotlight

Due to the difficulty of accurately steering and controlling most of the vehicles in Vice City, “G-Spotlight” presents a major challenge. The mission calls for doing parkour-like stunts over several buildings on a motorcycle, which is nearly impossible to properly aim at such high speeds. More times than not, a player will simply fly off the edge of the building to their sudden doom.

The only way to defeat the mission is to stop between each jump, realign the motorcycle accurately, and proceed with caution. However, that takes all the fun out of the mission. Another way to decrease difficulty is for a player to use a Police Maverick to collect Jumps, but this will subtract the Unique Jump Bonus points.

9 Bombs Away

“Bombs Away” is one of the most frustrating missions in Vice City, as it requires players to fly a mini RC plane out of the back of a van. With no room to maneuver and impossible vehicle mechanics to control accurately, multiple attempts will be required to defeat the task, especially while being shot at in the process.

Thankfully, a glitch in the PC version of the game allows players to exit the Fun Top Van by hitting the escape button as soon as the superb Cutscene ends, allowing players to spot and kill the Cubans on their own.

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8 Cop Land

“Cop Land” is one of the most agonizing missions in Vice City. Tommy must deliberately earn a wanted level from police, lead two cops into a parking garage, steal one of the cars and plant and detonate a bomb in Tarbrush Cafe, and escape back to Starfish Island unharmed. Good luck.

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The mission is so hard to complete because if Tommy leaves Lance too far behind, he will automatically die and the mission will end prematurely. Pacing is the key, but if Tommy is too deliberate, the cops and FBI will kill both of them on site.

7 Naval Engagement

The difficult objectives of “Naval Engagement” require Tommy to meet Rico, kill every Haitian on the boats, obtain the cases of cocaine, and return the contraband to Umberto unscathed. The multitude of tasks makes it one of the more challenging missions to complete in a single go.

The sheer amount of armed Haitians and shotgun-wielding Sharks that ambush Tommy make it very hard to survive. Even if he does, steering the Landstalker boat is not ideal for chases and often capsizes, rendering the entire mission moot. Using a rocket launcher to eliminate the Haitians is a smart move.

6 Dildo Dodo

Controlling the seaplane in Vice City is one of the most thankless and arduous tasks the game has to offer, never more apparent than in the “Dildo Dodo” mission. The task requires a player to fly a seaplane accurately through several multicolored circles to gain points, which is almost impossible due to the rudderless volatility of the seaplane. It may be one of the best GTA missions that don’t involve a crime, but it’s no easy feat.

Twisting, turning, cavorting, and diving the plane is far too difficult to perform successfully the first go around. A player’s best bet is to use the awesome GTA cheat codes to obtain a Dodo plane first, practice guiding it accurately, and then return to the mission to beat it.

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5 The Driver

“The Driver” is often considered one of the hardest missions in Vice City for a variety of reasons. Tommy must beat Hilary in a timed race through Vice City Beach while driving a Sentinel to her Sabre Turbo, which presents a major speed disadvantage. The Sentinel’s lack of handling and maneuverability makes it even harder to compete.

The biggest challenge of the mission is the relentless pursuit by the police, who will be on a player’s tail as soon as the race starts and will run players off the road and make it extremely hard to beat Hilary on time.

4 Hit The Courier

“Hit the Courier” provides the double difficulty of controlling a vehicle while accurately dropping bombs as the vehicle is in motion. Tommy must waylay a cadre of female guards in order to procure counterfeit plates. Afterward, he must kill the courier and flee the docks with the goods via helicopter.

Aside from the clunky controls of the helicopter that makes the escape portion of the mission very hard to complete, players will need to stay on guard and survive an intense shootout from all angles. Killing the courier with a sniper rifle is the smart play, but surviving the female ambush and making an escape without downing the chopper is no easy feat.

3 Death Row

Timed missions are always the most difficult to complete, and Vice City‘s “Death Row” is aptly named for the number of times a player will die trying to finish the task. First, Tommy must race to the junkyard to save Lance from certain death, keeping an eye on his health meter as drives perfectly through the city. Hitting cars and buildings will slow Tommy down and cost Lance his life.

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The second part of the mission is even harder, requiring Tommy to defeat a throng of heavily-armed baddies by his lonesome in the junkyard and do so before time runs out and Lance’s life fades away.

2 Keep Your Friends Close

Almost every Vice City fan will agree that “Keep Your Friends Close” is among the three most difficult missions in the beloved open-world game. Indeed, the final task of the entire game is an ultra-violent Scarface-like shootout that requires Tommy to blast through a mansion full of armed guards and murderous mafiosos.

The indefatigable onslaught of gunfire from every direction makes it almost to beat in the first attempt. Having a full arsenal and a loaded health meter is the only chance of surviving the hail of bullets, otherwise, a player will have to get extremely lucky to finish the job in short order.

1 Demolition Man

Universally considered the hardest mission in Vice City, “Demolition Man” is no fun at all. The task requires players to plant four bombs in a construction site in seven minutes flat. The kicker? The player has to do it by controlling a helicopter inside the building site while being attacked by angry construction workers armed with rifles.

Controlling the RC Goblin helicopter in Vice City is extremely cumbersome in the air, never mind inside a building. A player’s best bet is to go to Escobar Airport and practice via the RC Raider pickup side mission.

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