* AlternativeCharacterInterpretation: Donald Love didn't have much CharacterDevelopment in ''III'' and ''Vice City'', but he's really weird in this game.
** Toni Cipriani: a righteous man who delights in only committing atrocities because he just follow orders. Or he is a PsychoForHire? Toni is probably the protagonist who committed the greatest atrocities in the GTA canon, including killing a man with an ax and carrying his remains to a butcher shop. Remember, this was done intentionally and not to follow an order, not to mention several atrocities that go by Donald Love and Ned Burner's orders. While he still repents of his sins in a confessional, he never sought redemption when he bombed the area of Fort Staunton.
* CompleteMonster: [[CorruptCorporateExecutive Donald Love]] somehow manages to reach a special level of evil despite living in a CrapsackWorld populated with gangsters, [[SerialKiller serial killers]], and [[AxCrazy psychopaths]]. Introduced in ''VideoGame/GrandTheftAutoIII'', and having a cameo in ''VideoGame/GrandTheftAutoViceCity'', Love at first seems fairly standard for the series, arranging a gang war between TheYakuza and TheCartel just to lower property values. Though, at the time it was hinted he had [[ImAHumanitarian more sinister appetites]]. This is eventually confirmed in this game, where he's shown feasting on corpses and sending Toni Cipriani to collect bodies for him to devour. Aligning himself with [[TheMafia the Leone crime family]], Love runs in the race for mayor, sending Toni Cipriani out to murder his rival's campaigners. Losing his fortune in his failed campaign, Love makes plans to regain his fortune, with his first step being to [[BastardUnderstudy murder his mentor]], real-estate tycoon Avery Carrington, in order to steal his city development plans. He then has Toni recover Carrington's body to cannibalize later. Love's [[MoralEventHorizon worst crime]], however, is masterminding the deaths of thousands of people through the bombing of the heavily-populated Fort Staunton city district, just so he can make money off of redeveloping the district. A thoroughly depraved man, Love would stoop to any low imaginable to [[{{Greed}} fill his pockets]] or [[ItsAllAboutMe glorify his ego]].
* GameBreakingBug: Using cheats can possibly render the penultimate mission unwinnable, a concious choice by the developers.
* GoodBadBugs: With a lot of skill and practice, players can obtain a fully functional helicopter in two different missions, which can even be stored in your garage.
* JerkassWoobie: Salvatore Leone.
* MoralEventHorizon: Paulie Sindacco intersects the horizon with the attempted murder of Salvatore, sending his henchmen to take him to the crusher.
** Toni's mother has probably crossed the line with the attempted murder of her own son for not being "man enough".
** If there was a point where Donald Love had crossed the line, it was when he planned and executed the bombing of the Fort Staunton city district, killing potentially ''thousands'' of people, just so he can earn a buck over its redevelopment.
* NightmareFuel: Several thing that makes Toni Cipriani pure Nightmare Fuel. This is evident in the mission "Dead Meat", where he kills a man with an ax and dismembered him, and takes over his remains to a butcher for his remains to be sold.
* PortingDisaster: Continuing the trend of mobile ports of GTA games being inferior to console & PC counterparts, ''Liberty City Stories'' on iOS & Android is an extremely nasty port, because apart from having the same problems as the previous games, it also has very limited graphics settings & compatibility issues with some phones & tablets (particularly with Mali GPU devices), where the game refuses to work anywhere past the main menu. The fact that the port of Liberty City Stories was made by a different studio, Lucid Games, instead of the usual War Drum Studios, doesn't help. Possibly justified, considering this game was only released on the PSP & the Playstation 2 beforehand.
* ThatOneLevel: This game has several, the most notable being "The Portland Chainsaw Masquerade" where Toni is tasked with killing a large group of chainsaw-using madmen.
** What gives this mission its notoriety is that the whole mission, for some reason, is played from a birds-eye perspective, which increases the difficulty. On top of this, one slice from a chainsaw nearly kills you, even with full health and armor, and once you're hit, the others attack too. The only simple strategy is to sprint around in circles and hope that you have enough time to shoot one of them.
** The mission "Shoreside Redemption" isn't very popular either. The mission itself is fairly standard, if a bit difficult. You are tasked with escorting a newly aqquitted Salvatore to the courthouse in a police car while goons try to ram the prisoner transport van off the road. What makes this mission so notorious is the fact that using cheats can make this mission unwinnable, since Rockstar implemented a unique fail scenario for players trying to take the easy way.
** "False Idols" is another one. You have to locate and kill three different characters, (one of them in a ''helicopter'') before any of them reach their destination. What makes this one especially hard is that all three of them come from different islands, and killing them all requires memorising their routes, not to mention the fact that one enemy is in a bulletproof car, which forces you to waste precious time trying to ram the car off the road.
** "Dead Meat" isn't that difficult, but it can really throw off inexperienced players. You have to stalk Giovanni Casa through a maze-like sawmill, using the game's (non-existent) sneaking mechanics to take Casa by surprise, all while some idiot constantly reveals your location.
* ThatOneSidequest: The game ramps up the difficulty for obtaining some of the hidden packages to an almost insane level. A hidden package located on top of a gas station roof in Portland is considered particularly difficult to reach, and even GuideDangIt assistance is unhelpful.
* [[TheyWastedAPerfectlyGoodCharacter They Wasted A Perfectly Good Location]]: Considering you could steal helicopters & fly them in some missions, the lack of helicopters and/or rideable small planes in Francis International Airport is kind of glaring.
* TheScrappy:
** Ma Cipriani, Toni's domestic mother is this to some fans. Mostly in the early of game berating Toni for not being fearless like his father even though he killed countless enemies to accomplish goals. Her scrappiness reaches to [[UpToEleven extreme levels]] when she decides to call hit on her own son wanting Toni to die like "real man". On bright side, when Toni becames made man she calls hit off and she is never seen nor heard ever again.
** Vincenzo, who is heavily implied to be GreenEyedMonster. At first, it's ambiguous whether he really set Toni up to be arrested by police or not, causing Toni to be pissed off at him and crushed his car. Then, because of this, he tried to kill Toni. He failed.
** As if she wasn't bad enough in GTA III, Maria is worse in this game. Some of Toni's problems are because of [[NeverMyFault her screw-ups]].