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1* AccidentalAesop:
2** For a game that created a lot of controversy, there is a very strong anti-drug message in that all of the gangs besides the antagonist Colombian Cartel and their allies, the Yardies, Triads, and Purple Nines all want the drug SPANK destroyed instead of duplicated, and one mission has you face SPANK-addicted suicide bombers who are too strung out to even know what they are doing. Some other missions have you partaking in a civil war between subfactions of the Southside Hoods and siding with the group who opposes the distribution of SPANK (the Red Jacks).
3** The game also has a BeingEvilSucks theme going on, as Claude is [[ChronicBackStabbingDisorder betrayed on multiple occasions]] and betrays people in turn on his quest for revenge against Catalina. By the end of the main story, he's wanted dead by most of the gangs and there isn't [[VengeanceFeelsEmpty much of a sense of victory]] besides getting a net $500,000 cash reward and easy access to a Rhino Tank at Phil's army surplus base.
4* AlternativeCharacterInterpretation:
5** Claude's character in general is extremely open to interpretation given his status as a SilentProtagonist. This is intentional as according to WordOfGod, Claude's character is deliberately vague because they are an AudienceSurrogate, and that whatever is there for Claude is up for the player to project onto.
6*** Cold blooded maniac? Emotionless monster whose only joy is violence? EvilGenius [[EvenEvilHasStandards with standards?]] It's really up to the player to decide.
7*** Did Claude really [[spoiler:shoot and kill Maria]] at the end of ''III''? When [[WordOfGod God]] finally got around to answering questions about it, he just [[ShrugOfGod shrugged]].
8*** Adding to that, did Claude do all of what he did just to get back at Catalina? Or did he genuinely care about Maria enough to save her from Catalina's doom? The [[ShrugOfGod Shrug of God]] ending complicates this further.
9** Joey Leone is commonly seen as someone who's not very involved in the family business, preferring to work on his garage business. However, [[https://www.youtube.com/watch?v=5HKi0xP9XpM another interpretation]] is that he's much more involved than he lets slip, but he's maintaining (to a certain extent) his cover of a simple mechanic that runs his own garage. Some of his jobs aren't as trivial as they seem (such as dealing with the Forelli mafia remnants, or getting rid of one of the ways the Cartel is using to distribute SPANK in Portland), and Joey has more reasons to keep his cover against a newcomer than Toni or Salvatore (by the time Claude meets them, he's already proven himself to the Mafia).
10** In the final mission from Salvatore, [[spoiler:the car left for Claude is booby-trapped courtesy of Salvatore himself wanting to kill him. It is ambiguous on whether or not 8-Ball was aware of Claude being the target or if 8-Ball ever were the one who planted the bomb to begin with, especially since he will always be available to rig any car Claude brings with explosives even after Salvatore's death]].
11* CatharsisFactor: [[spoiler: Killing Catalina, especially after seeing how she acts in ''VideoGame/GrandTheftAutoSanAndreas'']].
12* CommonKnowledge:
13** It's commonly known that Claude betrays everyone he works with who doesn't betray him first, but this just isn't the case. Over the course of every single mission, he only betrays a single person: Kenji. And that's on Donald Love's orders. Beyond that one instance, all the betraying is done to Claude, and he leaves numerous mission chains either on friendly terms, or with something happening to the mission giver that renders them unable to have a further relationship.
14** It's commonly known that the cut character Darkel was cut due to the September 11 attacks. In fact, he was cut because his missions just did not fit the game's atmosphere.
15* CompleteMonster:
16** [[AxCrazy Catalina]] is a {{sadist}}ic, [[AmbitionIsEvil ambitious]], [[HateSink hateful]] thief and SpreeKiller turned [[TheQueenpin boss]] of TheCartel, who started her career in [[VideoGame/GrandTheftAutoSanAndreas San Andreas]], purposefully escalating the violence in her robberies, killing numerous bystanders and cops with glee. Having a history of using and discarding her boyfriends and partners, Catalina shoots protagonist Claude, leaving him to die during a robbery, before rising through the ranks of the Colombian Cartel and abandoning her next partner, Miguel, later killing him. Catalina starts an empire, flooding Liberty City with the especially potent and mentally deteriorating drug, SPANK, [[EvenEvilHasStandards turning even]] the [[Characters/GrandTheftAutoLeoneCrimeFamily Leone Crime Family]] and {{Yakuza}} against her. Among her distribution methods, Catalina spikes SPANK through coffee shops and street vendors across the city. Encountering a vengeful Claude, Catalina drugs multiple addicts into crazed suicide bombers to try to kill him. Out of spite, Catalina then abducts Claude's alleged girlfriend Maria, attempting to lure him into getting executed.
17** Donald Love. See [[YMMV/GrandTheftAutoLibertyCityStories here]].
18* DemonicSpiders:
19** Any {{mook}} with an M16 is this. They can shred you apart and waste you in seconds before you can get a chance to react. Even if you have full armour/health, you can be killed in seconds if you're careless.
20** [[spoiler:Mafia goons]] earn this distinction with flying colors once you have earned their eternal vendetta against you. They all have [[ShotgunsAreJustBetter shotguns]] and [[TheAllSeeingAI even if you're in a vehicle]], they'll immediately recognize you and open fire. Two solid shots will [[MadeOfExplodium end your drive in a deadly explosion]], unless you are in a Rhino tank [[spoiler:or have unlocked special vehicles that are bulletproof]]. Additionally, if you're on foot, their shotgun blasts will likely [[ScrappyMechanic knock you down]] [[CycleOfHurting and prevent you from moving while they close the distance]]. They will probably knock you down again if the shots don't kill you. Simply put, after you [[spoiler:kill Salvatore]], you'll never be able to set foot in [[spoiler:the Saint Mark's district]] ever again. For this reason it's absolutely imperative that you finish all of Portland's side missions (e.g. Ambulance, Taxi, and Vigilante) before you unlock Staunton Island. You can see how bad it is [[https://www.youtube.com/watch?v=hzRS403BB68 here]]. Oh and to rub salt on the open wound, no, they were not nerfed in the Definitive Edition.
21* DifficultySpike: While the first couple missions are pretty short and simple and let you get used to the controls, "Bomb Da Base: Act II" is where the difficulty really ramps up as the enemies become more heavily armed and gangs start becoming hostile to you.
22* DisappointingLastLevel: Staunton Island and Shoreside Vale are increasingly less detailed compared to Portland's bustling activity, varied scenery, and things to do. This is probably one of the reasons why Liberty City was revamped from the ground up in ''VideoGame/GrandTheftAutoIV,'' even if that effectively meant putting the game in its own continuity.
23* EnsembleDarkhorse:
24** Asuka for her dominating personality and being one of the very few bosses who shows respect to Claude. Most fans wished she was involved in the other 3D era games.
25** The trenchcoat-wearing, hillbilly pedestrian known as the "Creepy Old Guy" thanks to having a lot of goofy lines that he often spouts out of nowhere. "MY MOTHER'S MY SISTER!" is possibly his most memorable line.
26* FanNickname:
27** Due to being ordered around for the entire game, before his real name was revealed, Claude was referred to as "Fido", the name Maria refers to Claude as when he is ordered by Salvatore Leone to be her driver.
28** The area where the game's opening scene where Catalina betrays Claude has been dubbed "Ghost Town" not only due to the area being inaccessible through normal means, but the area itself is barren without any sign of life if one were to access the area.
29* FranchiseOriginalSin: ''Grand Theft Auto III'' was hardly the first violent, M-rated video game to raise eyebrows; ''Doom'', ''Mortal Kombat'', and ''Duke Nukem'' have it beat on that front by several years. However, it was the first such game to become a mainstream pop culture sensation on the level of ''Pokémon'' and ''Super Mario Bros.''. It was both acclaimed by critics and railed against by MoralGuardians for the then-unprecedented freedom it offered to gamers, which included all manner of violence and debauchery. Ignoring the many direct ripoffs that came out in the early-mid '00s, the success of ''Grand Theft Auto III'' has been pointed to as being responsible for the proliferation of RatedMForMoney attitudes among both developers and gamers who demanded more "mature" (i.e. "rated M for Mature") content in games.
30* GameBreaker:
31** The M16. It is extremely unbalanced, deals a lot of damage and can shred apart cars, people and any form of law enforcement with its ridiculous rate of fire. It renders most bullet weapons and the Shotgun obsolete, the exception being the Uzi for drive-bys and run-and-gun play. It's no surprise why it was {{nerf}}ed in ''[[VideoGame/GrandTheftAutoViceCity Vice City]]''.[[note]]In a way, this weapon became the Minigun in ''Vice City'' -- the rate of fire remains similar, but the "magazine size" and even the caliber has been increased tremendously. However, it could still be a GameBreaker if you were playing the PC port of the game with a mouse, since you could aim it with sniper-accurate precision.[[/note]]
32** The Shotgun. It can destroy a vehicle with just two or three shots, it can easily knock down any pedestrian on foot, and its blasts can [[CycleOfHurting stunlock]]. It is not as powerful as the M16 but still a very lethal weapon. It's even worse when you know how to {{lag cancel}} the firing/reloading animation by switching or toggling lock-ons. This trick however is rendered impossible to do in the mobile version with the touch controls and near-impossible to perform consistently with a controller thanks to using an automatic targeting system.
33** The Rhino Tank. Without the use of cheats it is extremely hard to acquire -- you have to either beat the game or reach a full six-star wanted level and steal one from the military, with the latter that can be used to complete the emergency vehicles side-quest to allow you to drive one before beating the game -- but once you are in one...
34### Every vehicle, including all law enforcement (besides other tanks), blows up when it touches it.
35### The turret is as strong as a rocket launcher, blowing up anything in one shot.
36### You have unlimited ammo.
37### The tank is EXTREMELY hard to blow up by law enforcement and gang members (though it is extremely vulnerable to fire, like from Molotovs), and reaching a 6 star wanted level is a breeze.
38### Firing the turret creates recoil, which slows you down if it's pointing forward. If you point the turret backwards, however, firing it repeatedly will make you go absurdly fast.
39** The Banshee. It isn't the fastest car in the game and it has very low health, but its incredibly high acceleration and good handling make up for that, especially since a decent portion of Liberty City is made up of short, tight streets. Combine this with how there is an easy spawn for the Banshee on Portland Island[[note]]The Capital Autos showroom in Harwood[[/note]], and the car is fairly common on the other two, you will never need another car in most scenarios.
40** Obtaining all of the Hidden Packages is quite an undertaking without a guide, but should you collect all 100 at the earliest opportunity (typically by looking at a map with all the packages marked), you'll have every weapon in the game at all of your hideouts and never have to worry about ammo ever again. It makes the final mission easier as you can drive to your nearby hideout, regain all the guns you lost and have some ammo to work with, and go complete the mission. The major game breaker is the free M16 ammo you can collect.
41** On the PC version, players can take advantage of the free aiming controls the mouse and keyboard scheme has to offer, not only for being able to strafe around enemies, but also the pin-point accuracy with weapons, which the game wasn't designed around for.
42* GoddamnedBats:
43** The Triads. They're likely going to be the first gang you piss off. They're not very tough by themselves, armed only with bats and pistols, but their territory covers almost half of Portland, making moving around it for the remainder of the game's first chapter a pain.
44** Some pedestrians will start attacking the player when provoked by using explosives or blowing up vehicles that also end up killing others.
45** When you get the wanted level that is higher than two stars, the police will finally start focusing on you, and it shows. The patrol cars are very fast and attack in packs, trying to ram your vehicle off the road and even turn it over. Thankfully, a visit to Pay 'n' Spray will throw them off the hook... unless you happen to drive any emergency vehicle other than a taxi or a FBI car, at which point you will have to look for police bribes around the map. It gets even worse when you are harassed by the cops in the middle of a mission.
46* GoodBadBugs:
47** Due to the way normally unusable special vehicles and garages work, you can gain access to a number of cars with unique properties by first wrecking said cars near a garage and then using a sufficiently heavy vehicle to push them in far enough that the door closes: once it opens back up, they'll be as good as new and their doors will be unlocked, allowing you to drive around in the only car in Liberty City [[MundaneMadeAwesome with working door locks]] the police can't figure out how to open when trying to bust you or ones that're [[NoSell immune to]] [[ImmuneToBullets bullets]], flames and/or [[NonFatalExplosions explosions]].
48** The PC version makes the Firefighter mission unintentionally much easier due to the way the replay function works. You put out a fire, hit F1 the moment another car on fire is reported, rinse, repeat. The game thinks the replay is an actual fire being put out, giving you credit.
49** Also on the PC version has a bug with the pause menu that makes the "Vigilante" mission. If you pause the game near the suspect's vehicle, you can cause the suspect to bail out and cause him or her to run away. This is really useful to get the police bribes at your hideout.
50** When in any vehicle with an available Vehicle Mission, holding down the 'start mission' button, exiting the vehicle and entering another, only then letting go of the button, will let you play that Vehicle Mission in any vehicle you wish. This is particularly a godsend for Taxi Driver, where you can significantly speed things up by doing it in a Banshee or Infernus.
51** Ordinarily, you hold down the Sprint button to haul ass when on foot, until Claude slows to a run again (even hunching over and panting if you come to a stop). However you can mash the button to sprint infinitely, which renders finishing the [[ThatOneSidequest Paramedic sidejob]] completely pointless, except to give your fingers a rest if you lack a turbo controller.
52* GrowingTheBeard: No kidding. [[VideoGame/GrandTheftAutoClassic The first]] [[VideoGame/GrandTheftAuto2 two]] games were, while very innovative, significant games and fairly charming in their own way, were still extremely rough, [[NintendoHard nigh-on impossible]], clunky, dated, and simplistic games that [[NoSuchThingAsBadPublicity largely only sold well due to the massive amounts of controversy]] they had caused. Meanwhile, ''III'' brought [[VideoGame3DLeap the series into 3D]] in glorious form, massively increased the length, scope, and depth, brought in incredible production values with legitimately well directed, well-acted cutscenes, added in much of the humor and satire the series is known for, and restructured the game into a format that, while still challenging at times, was much less unforgiving and sadistic than the first two games were. While OnceOriginalNowCommon is in effect these days, there's a good reason why ''Grand Theft Auto III'' is considered one of the greatest and most influential games of all time and turned the series into one of the industry's biggest juggernauts.
53* HesJustHiding: There are some people who think that [[spoiler:Catalina survived having her helicopter shot down in the final mission. The fact that [[NeverFoundTheBody her body was never found]] might be a significant factor to the theory]].
54* HilariousInHindsight:
55** [[Film/Drive2011 A stoic, quiet man wearing a recognizable jacket embarks on a personal revenge quest]].
56** Rockstar would later revisit the idea of [[VideoGame/RedDeadRedemption a man whose past includes a failed robbery going after his former allies]], although the context is completely different.
57** One of the in-game commercials features the "[[HummerDinger Maibatsu Monstrosity]]", which served as a TakeThat towards the [=SUV=] craze back in the late 90s to early 2000s. More than two decades later, the "San Andreas Mercenaries" update for ''VideoGame/GrandTheftAutoOnline'' introduced a "sportier" version of the former known as "[[https://gta.fandom.com/wiki/MonstroCiti MonstroCiti]]" (based on the Mitsubishi Pajero/Montero Evolution rally raid) which doubles as a CallBack.
58* JerksAreWorseThanVillains: It's difficult to truly dislike Catalina, despite how treacherous she is and having flooded Liberty City with SPANK. Kenji Kasen, on the other hand, is a very unlikable and unthankful {{Jerkass}} who uses Claude as a scapegoat for his own gang's mistakes.
59* LadyMondegreen: With all the NPC dialogue present, there's bound to be some misheard lines.
60** "My tuba!" [[note]]My toolbox![[/note]]
61** "NO MONEY, NO PROBLEMS."[[note]]MO' MONEY, MO' PROBLEMS![[/note]]
62** "Rammin' Steve!" [[note]]Ram and speed![[/note]]
63* LesYay: Asuka and Maria certainly seem to be more than friends, but it's never confirmed outright.
64* MemeticBadass: [[https://youtu.be/Irand6AtDYQ The creepy old man pedestrian]], otherwise known as the "MY MOTHER'S MY SISTER" guy. ''Everyone'' in Liberty City (sans Claude, of course) is afraid of him and will run away if he picks a fight, ''[[HorrifyingTheHorror even the police and gang members]]''.
65* MemeticMutation:
66** "Hey, I'm bored. When are ya gonna drill me?"
67** "MO' MONEY, MO' PROBLEMS!"
68** "MY MOTHER'S MY SISTER!"
69** "My toolbox!"
70** "I DON'T KNOW WHERE I AM AND I'M HUNGRY!"
71** [[Film/{{Scarface1983}} "You want the chainsaw, gringo?"]]
72* MoralEventHorizon: [[MoralEventHorizon/GrandTheftAuto See here.]]
73* {{Narm}}: In the final story mission, the shot of Claude sucker-punching a Cartel who's about to shoot him is done in slow motion. This was likely to make it appear more dramatic, but the effect looks sillier than anything with the game's dated graphics and the fact that this was reserved for the death of a nameless mook. Never mind how the thug takes his sweet time shooting an unarmed man at point blank range.
74* OnceOriginalNowCommon:
75** Inevitable, considering the game's age and how both the ''Grand Theft Auto'' series and WideOpenSandbox have evolved over the years. Liberty City is comparatively small, the shooting mechanics are very simplistic, the story is disconnected and is more of an ExcusePlot than anything, and the missions feel very basic in comparison to the [[VideoGameSetPiece set pieces]] employed in future titles. But back when it was released, this was considered to be a very awesome game that allowed for an unprecedented level of freedom with how it combined driving, exploring, and shooting in one seamless package, with nigh unlimited VideoGameCrueltyPotential to boot.
76** While ''Grand Theft Auto III'' has a good share of laughs, most of them are relegated to the radio. Story cutscenes focus mostly on the boss in question briefing Claude on his next objective, and they seldom feature the interactions between characters that are necessary for humor. Even the jokes on the radio are notably dry and down to earth. Considering how DenserAndWackier things would become in the future, ''Grand Theft Auto III'' feels notably somber and oppressive in comparison.
77** Speaking of the radio, the amount of licensed songs the game features was impressive at the time, but it would immediately be one-upped by ''Vice City'', whose radio features over three times the amount of songs from a wider variety of artists, albums[[note]]Flashback, K-JAH, and MSX FM all consist of songs from one album each[[/note]], and record labels on top of the songs licensed for ''Vice City'' being far less obscure.
78* PolishedPort:
79** The PC version features support for higher resolutions and greater draw distance, the ability to use your own [=MP3s=] for the game's music, and adds a new control scheme for keyboard and mouse that works wonders for the game's combat. There's even limited CharacterCustomization in a roundabout way if you're willing to play around with character model files. It does however have some glaring issues, such as broken widescreen support, missing lighting effects, compatibility issues with newer Windows systems, and in the Steam version, cars are rendered much darker for no discernible reason while fixing the headlights bug. Thankfully, these issues can easily be fixed thanks to [[https://thirteenag.github.io/wfp#gta3 ThirteenAG's Widescreen Fix]], [[https://gtaforums.com/topic/669045-silentpatch/ SilentPatch]], and [[https://github.com/aap/skygfx_vc/releases/ SkyGFX]], while [[https://gtaforums.com/topic/562765-ginput/ GInput]] can bring back classic console-styled controls and more for modern [=XInput=] controllers.
80** The original Xbox port has lower draw distance and somewhat different lighting compared to the [=PlayStation=] 2 release, but more than makes up for these cutbacks with revamped visuals featuring higher poly models with articulated hands on characters, higher resolution textures, spectacular lighting and reflections added to many vehicles, enhanced effects, and also features the ability to use your own music stored on the system's hard drive.
81** The version available on Android and [=iOS=] devices has completely customizable controls (both touch interface and external controllers are supported), visuals comparable to the Xbox port, adjustable graphics for ease of use on a large range of devices, minimal loading, improved graphics on the higher settings, and new to the Android and [=iOS=] version, the ability to move the camera around freely while driving, plus a freely accessible in-game map of Liberty City with makers of important locations such as the safehouses, Ammu-Nation, and Pay 'n' Spray shops, which the previous versions lack. On top of that, it allows the player to keep all weapons they had when they were killed or arrested.
82* PortingDisaster: The Trilogy Definitive Edition. On one hand it backported almost all of the Polished Port features detailed above. On the other hand, see the YMMV page for the whole series for details.
83* QuestionableCasting: The AxCrazy BigBad Catalina is voiced by soul singer Cynthia Farrell in her first acting role outside advertisement jingles and voiceovers. Administrivia/TropesAreNotBad however, as Catalina turned out to be one of the most memorable characters in the franchise and her voice acting is easily one of the highlights in this game.
84* TheScrappy:
85** Kenji Kasen. An [[UngratefulBastard ungrateful prick]] with an annoying voice who doesn't care how much Claude does for him, going so far as to blame ''[[TheScapegoat him]]'' for the Yardies continuing to ally with the Cartel despite the former being framed for the murders of several Cartel members (done by Claude under Kenji's orders, no less). Thankfully, [[spoiler:[[TakeThatScrappy Donald Love orders Claude to kill him]]]].
86** [[spoiler:Maria.]] [[spoiler:She is [[TheMillstone the source of many of Claude's troubles.]] Overlaps with DamselScrappy in the finale, and it doesn't help that she was [[KickTheDog Kicking the Dog]] right before that by assisting Asuka in torturing Miguel (who was blamed for Kenji's death due to Claude killing him under Love's orders). Some fans are even thankful Claude might have [[TakeThatScrappy shot and killed Maria]] during the credits.]]
87** King Courtney certainly qualifies for [[spoiler:betraying Claude due to allying with Catalina offscreen, rendering his entire mission chain pointless]]. Worse, he [[KarmaHoudini never suffers repercussions for it]].
88* ScrappyMechanic:
89** Gang hostility. As you go through the story, you'll eventually anger a gang into shooting you on sight, and there's no way to undo this. By the end of the game, all but two of them [[note]](the {{Yakuza}} and the [[GangBangers Southside Hoods]])[[/note]] will want you dead, and you can't go anywhere in the city without being shot at (and you can forget about going into [[spoiler:Saint Mark's District]] where the [[spoiler:[[DemonicSpiders shotgun-wielding Mafiosi]]]] are), which can make completing some side missions difficult if not outright impossible. Later games in the series let up on this by reducing the number of gangs that want to kill you (it's exclusively the Haitians after finishing the Gang War sidequest in ''VideoGame/GrandTheftAutoViceCity'' and the military if you enter the base without the police uniform), or introducing the ability to take over turfs (''Videogame/GrandTheftAutoSanAndreas'').
90** This is the first ''Grand Theft Auto'' game to have the infamous Sprint Meter. However, completing the [[ThatOneSidequest Paramedic sidequest]] grants you infinite sprinting ability. [[GoodBadBugs Or you can also just hammer the Sprint button for infinite sprint anyway, due to an oversight.]]
91** It's relatively common for parked cars to have car alarms, forcing the player to either get back out and stand there for several seconds until it turns off or drive around while the alarm is going off, which will alert any law enforcement who see you that you just stole it. Thankfully later games didn't have every third car start going off when you got in.
92** Parked police cars and ambulances have a seemingly 50/50 chance to be locked, and thus inaccessible without breaking off their doors (which is easier said than done). There isn't any particular reason for why these two specific vehicles have this quirk when nothing else does, and all it does deny you from starting Paramedic/Vigilante and using two of the faster vehicles in the game at complete random. Not a game-ruiner, but certainly annoying, and future games scrap this quirk.
93* ScrappyWeapon:
94** The pistol is outclassed by every other firearm in the game. With mediocre rate of fire and only decent damage, it's immediately rendered obsolete by the Micro Uzi, as the latter is also usable from inside a vehicle and boasts more than twice the rate of fire. ''Vice City'' corrected this by offering the Colt Python as a heavy-hitting magnum upgrade over it, in exchange for zero mobility while firing, and a smaller magazine, while ''San Andreas'' allowed the regular pistol to be dual-wielded unlike the Desert Eagle that replaced the Python.
95** The Flamethrower is nothing like the one from the 2D games. Its range is greatly nerfed, meaning you're more than likely to accidentally set yourself on fire than trying to set enemies on fire. This becomes more evident that it will likely get you killed if you use it too close to a crowd of enemies. Unlike future ''Grand Theft Auto'' games, there's no fireproof bonus.
96* SequelDisplacement: The game was and is more popular than its predecessors by an order of magnitude.
97* ThatOneLevel: [[ThatOneLevel/GrandTheftAuto See here.]]
98* ThatOneSidequest:
99** While most side missions requiring a visit to [[spoiler:Mafia]] territory can done before you [[spoiler:kill Salvatore and have the territory filled with hostile shotgun-wielding wise guys]], King Courtney's "Gangcar Round-up", which has you steal a [[spoiler:Mafia]] car, can only be done after you do so. "Rigged to Blow" by D-Ice, which also can only be done after [[spoiler:killing Salvatore]], luckily averts this, for the most part. While the final destination of the job ''is'' within the [[spoiler:Mafia]] territory, the gang AI for the duration of this job was altered to 'neutral'. This is a good thing, since the rigged sports car you're driving (under a time limit) can't take much damage before blowing up, meaning the job would be practically impossible to complete otherwise.
100** "Turismo" is one of the most troublesome missions in the game. It’s a street race, but there are several factors that combine to make it frustrating. First, traffic continues as usual and it is all too easy to hit the other cars. Your opponents also have Cheetahs, the fastest cars in the game, and they tend to deliberately crash into you to slow you down, though they are not immune from ArtificialStupidity.
101** "Big 'n' Veiny". You have to follow a long trail of porno magazines in a van with a high chance of tipping over. You have a strict time limit which goes up by one second for each magazine you pick up (so at least you can skip a few). The longer you wait to do this mission, the harder it gets: if you wait to do it until you get to Staunton Island, the route will take you through ''three'' gang territories (Diablos, Triads, and [[spoiler:Mafia]]), whose members will shoot your van. And if you happen to build up a wanted level, forget it. One silver lining is that [[spoiler:after the Mafia turns hostile after Salvatore's assassination, they only have Uzi 9mm pistols instead of shotguns for this mission.]] It can also be made considerably easier, albeit longer, if you know where the trail of magazines ends, because you can push the van over to your destination; the timer doesn't start until you enter the van.
102** The Paramedic mini-game is easily at its hardest in this game due to the wonky physics and the inability to repair or even change the ambulance vehicle (so if you are pulled out by an enemy gang member, your run is over). There is no map and the island layouts can thus be very confusing. The game also doesn't take the city layout into account, instead only calculating the timer according to their distance from the hospital, meaning that if you're given 30 seconds to reach an NPC who is nearby but can't be reached without a detour, you're pretty much fucked. Because of this system, Portland is probably the easiest island to complete the minigame in thanks to its small size, followed closely by Staunton Island which gives you a generous amount of time.
103** All of the vehicle checkpoint missions except "Multistorey Mayhem" are this:
104*** "Patriot Playground" has you go off-roading in Portland to hit 15 checkpoints off the coast near Saint Mark's. Half of the checkpoints are at the edges of cliffs or the tops of hills, making a preplanned route to meet the time limit necessary.
105*** "A Walk in the Park" is anything but. Not because of the mission in question, but it's a LuckBasedMission on whether the Landstalker flips over or not. If it does, then the mission ends.
106*** "Gripped!" has the checkpoints spread near the coast of Shoreside Vale. It's the danger of either accidentally rolling over the Patriot or driving into the water that are the real hazards. Much like "Patriot Playground," some of the checkpoints are near cliffs.
107* TheyWastedAPerfectlyGoodCharacter:
108** 8-Ball, who teamed up with Claude at the beginning of the game to escape and take out the SPANK shipment, yet disappears completely after that and is never even heard from. Many fans felt he should have stuck around with Claude for the remainder of the story to continue working as Claude's partner.
109** Sal's son, Joey, makes his first appearance in this game, yet is treated more as a minor character who barely contributes anything for the plot. The fact that he doesn't even appear in [[VideoGame/GrandTheftAutoLibertyCityStories the prequel of this game]] doesn't help matters.
110* UnintentionalPeriodPiece: Inevitably, with the game taking place in October 2001.
111** Claude uses a pager (and in some cases, a payphone box) rather than a cell phone to communicate. On Chatterbox, a MoralGuardians group leader against cell phones calls in to protest against them, but also talk about how difficult it is to communicate without them. Both of these elements have been dated past TheNewTens with many more people owning cell phones, and even more so by the fact almost every later game in the "''GTAIII'' era" of the series - despite being ''intentional'' period pieces dated even earlier than ''GTAIII'' - uses cell phones rather than pagers.
112** Several other topical references date themselves, with radio commercials alone satirizing the dot-com boom ([=PetsOvernight.com=], which delivers exotic animals overnight), [[HummerDinger massive SUVs]] (the aforementioned Maibatsu Monstrosity - its advertised mileage of ''3'' miles per gallon is [[ConspicuousConsumption treated as a point of pride]] in one commercial), dating services (Fernando's New Beginnings, a dating service which lets bored husbands secretly arrange for trysts with prostitutes) and the beginnings of RealityTV (''[[BloodSport Liberty City Survivor]]'', where 20 recently-paroled guys are equipped with heavy weapons and then dropped into the city to hunt each other down, with one commercial including a recommendation from [[SpectatorCasualty someone who got shot by one of the contestants]]). There's also the adrenaline pills, which in addition to [[QuadDamage boosting your melee strength]] put you into BulletTime - an obvious reminder of the days in the early- to mid-2000s where the influence of ''Film/TheMatrix'' reigned supreme.
113** Liberty City's portrayal as TheBigRottenApple, a view that started to fade soon after 9/11 (which happened a month before the game's release) and UsefulNotes/TheWarOnTerror. Even though the game was held back a month to [[DistancedFromCurrentEvents attempt to remove content that would look offensive after 9/11]], very little could actually be done with the small amount of time they had (the police cars were changed to a Los Angeles-inspired color scheme rather than emulating the NYPD's then-current and distinctive blue on white, airplanes couldn't be blown up, and the Dodo airplane flying over the city [[https://www.youtube.com/watch?v=czZP-3qWs5c has had its path edited]] so that it doesn't get close to any tall buildings), dating it to the immediate pre-9/11 period of 2000 to, at latest, August 2001.
114** The character of Donald Love is a ruthless businessman and owner of a large skyscraper who expresses a desire to instigate a gang war for property development. Love is quite clearly based on the [[{{Trumplica}} then-current pop-culture depiction of]] UsefulNotes/DonaldTrump, an eccentric businessman and real estate mogul, before he would become better known as a politician.
115* UnintentionallySympathetic: Salvatore, of all people, gets this from many. [[spoiler:While his attempt to kill Claude out of paranoia was a pretty bad decision, it has been shown that Salvatore has already been betrayed at least once by [[VideoGame/GrandTheftAutoSanAndreas C.J]], in the former case he even lost his casino's money, putting him in the right to be overly cautious and suspicious. Not to mention it was Maria who [[NiceJobBreakingItHero unintentionally caused the whole problem in the first place]] by telling Salvatore about her relationship with Claude in the open, making the subsequent events partially her own fault as well]].

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