Given the dark tone and Crapsack World nature of the game, especially compared to later Grand Theft Auto games, there are many things within Liberty City that can send chill down to your spine.
- Claude, a cold, remorseless, silent killer who doesn't give a damn about anyone he works for, so long as he's paid: when he finds better offers, he'll kill his old bosses without hesitation. He won't show any sign of remorse for his actions, only caring about getting back at his ex-girlfriend, Catalina. If he shot Maria at the end, then he doesn't even care about anyone trying to be friendly with him.
- The very atmosphere of the game. Similarly to Grand Theft Auto IV, the game has a bleak, eerie atmosphere, even in the daytime.
- Similarly to Grand Theft Auto: Vice City, blowing someone's head off is very graphic. However, this is the only game where you can outright dismember a person's limbs, and an explosion can easily tear their bodies apart.
- Some designs of the characters can be somewhat creepy, especially with their dated models.
- The final mission for King Courtney (Kingdom Come) is Nightmare Fuel dialed way past eleven. In this mission, King Courtney betrays you and allies with Catalina, making you fall into a trap with deranged drug-addicts who run to you and explode because they have bombs. If you played the game as a youngster, it's safe to say that you were not the only one who felt highly disturbed with this mission. Even worse, you can take this mission after Catalina's been killed, and you will still get ambushed by his goons because it was meant to be done before the final mission. Thankfully, if you've brought an explosion-proof vehicle, it is no longer terrifying as they can't just pull you out of the car.
- After you've killed Salvatore Leone, fighting against the soldiers of the Leone Family can be quite scary. Unlike other gangsters, these tough guys are armed not only with handguns, but also with shotguns. Even if you're in a vehicle, they'll immediately recognize you and open fire. Two solid shots will end your drive in a deadly explosion, unless you are in a Rhino tank or have unlocked special vehicles that are immune to gunfire. Additionally, if you're on foot, their shotgun blasts will likely knock you down and prevent you from moving while they close the distance and fire again.
- More terrifying yet? They are unstoppable. Even if you have killed a few, others will appear from corner to corner running towards you, surrounding you and they will not stop until you are killed.
- If you thought the Leone Family was bad, then you haven't seen the army that comes after you when you have the highest wanted level. When you see military trucks and Rhino tanks chasing you instead of LCPD patrol cars, SWAT vans and unmarked FBI cruisers, you know the authorities aren't fucking around anymore. Trying to survive a six-star wanted level out in the open is suicidal. If you are not in a Rhino tank or a vehicle that is immune to collision damage, odds are that other Rhino tanks will nuke your vehicle on contact. If you're on foot, the infantry armed with M16s, which can kill you within a second due to their shot-grouping and blistering rate of fire, will swarm you. M16s have enough DPS to shred any vehicle vulnerable to bullets in seconds. It's to the point that the military from Vice City and onwards have been nerfed to either use an MP5, or reduce the rate of fire from their M4/M16 if they are carrying it (San Andreas, Vice City Stories, and V).
- The piano track that plays inside Salvatore's mansion plays constantly, even after his death. There's a reason why visiting the house after "Sayonara Salvatore" can be rather creepy, especially when doing "Gang-car Round Up" mission for King Courtney, where going to the mansion's parking lot is one of the few ways to obtain the Mafia Sentinel safely.
- One of the most standout examples is a group of four hobos in the hidden tunnel beneath Saint Mark's district in Portland Island. They stand in circle surrounding a Hidden Package, and just stand there doing nothing. What's even scarier is that they drop molotovs upon death. Some players also claim that they never respawn again after you kill them and/or take the hidden package. Just what the heck are they? Some kind of a cult? Nothing Is Scarier, indeed. More info
- Marty Chonks, the near-bankrupt, Ax-Crazy owner of the Bitch'n' Dog Food factory in Trenton, kills people if they get on the wrong side of him; being the owner of a processing company, you can guess what he does to discard his evidence. That includes his banker whom he accuses of stealing funds from him, two thieves he hired to commit insurance fraud in the fear they could snitch out to him, and even his wife for her heavy spending, cheating on him, and for her life insurance. Bonus points for the fact his toothbrush-style mustache makes it fairly obvious to whom he resembles. Thankfully, the guy Mrs. Chonks was seeing, a loan shark named Carlos, introduces the business end of his shotgun to Marty after Claude takes him to the facility.
- The ending of the game has protagonist Claude finally killing Catalina. Afterwards, Claude and Maria walk together as they cross over to the other side of the Cochrane Dam. Maria can be heard talking until the screen cuts to black and a shot is fired. The game doesn't really explain what happens and whether Claude killed Maria or simply shot at a random direction to shut her up it's all up to the player's own conclusion. Even when Rockstar themselves are asked about Maria's fate, they don't provide a concrete answer.
