These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Sonny Forelli — a mob boss who is trying to crush Tommy's fledgling empire, or somebody who is justifiably concerned with the fact that a made man in his organization has built a criminal empire for himself in South Florida and is now openly defying his authority?
Tommy Vercetti — is he a smart entrepreneur who managed to live out the American Dream, or a jerkass thug who bought out the city and betrayed the men that he had sworn an oath to in the name of personal gain?
Examination of the motives of Sonny Forelli and Tommy Vercetti can easily turn them into, respectively, an Anti-Villain and a Villain Protagonist. Sonny sent Tommy down to Vice City to make a drug deal, and when it goes wrong, Tommy tells him that he will recover the money and the coke for him. However, Tommy then stabs him in the back by creating his own criminal empire in South Florida and keeping everything for himself. Sonny had every right to do what he did to Tommy and his business.
Although, it is heavily implied in the dialogue between the two in the final mission that Sonny set up the drug deal that landed Tommy in this mess to go wrong and did not intend for him to survive. It is also implied that Sonny had also set up the incident that landed Tommy in jail several years prior.
Lance Vance — a jerkass who betrayed Vercetti simply because he was a greedy bastard? Or, perhaps, his tragic life and drug use made him feel compelled to betray his colleague?
Best Level Ever: Vice City actually had many of these, "Publicity Tour", if not for the actual mission, then for the dialogue.
The actual mission arguably counts as well. Basically, you're escorting the band Love Fist to their concert, but their crazed stalker rigged the limo to blow up if you drive below a certain speed. So you're driving through town like a maniac, avoiding traffic and sliding in the rain (it's always dark and raining during this mission to conceal the game's graphical limitations: everyone in the car is technically sitting still) until the band figures out how to disarm the bomb. Definitely one of the more different GTA missions.
The fast-paced "Phnom Penh '86" could count as well. In a total reminiscence of Vietnam-era aerial raids, you team up with Lance and fly in a helicopter to a drug gang's stronghold of three mansions, and while Lance drives the helicopter you fire a M60 machine gun at fully-automatic armed gang members which continue to appear from the mansions corridors, terraces and backyards, you eradicate them.note Diaz "request" in the mission introductory cutscene. Also note that the mission's name is actually the capital of Cambodia, rounding off the "jungle war" theme. Bonus if played while playing Radio Espantoso's tropical songs, like Irakere's Anunga Nunga.
"Bombs Away!" arguably fills, you remote-control a RC toy plane carrying homemade bombs to sink escaping Cuban boats all while Cubans shoot at your plane with Ruger Mini-14 assault rifles from their boats, the charm is the GTA series introduction to an aeronaval styled combat. Bonus if played while playing V-Rock's song Megadeth's Peace Sells.
Hell, any RC mission can qualify (note that curiously they always feature carrying bombs...)
In "All Hands On Deck!" you again engage in aeronaval combat, you must protect Colonel Cortez in his way out of Vice City, which results in fighting in his yacht against a group of armed French agents which come aboard attacking from boats, helicopters and forming a boat's barricade to block Colonel Cortez's way out. Eventually an AH-64 Apache military helicoptercomes firing all over the yacht, and you must take it out.
Probably the most cool and badass mission in the entire game, "The Job", where you, Phil Cassidy, Cam Jones and Hilary King rob the Vice City's El Banco Corrupto Grante. The SWAT storming into the bank later makes it even more epic. This is the kind of mission that paved the way for Grand Theft Auto V's heist missions.
No love for the final mission, "Keep Your Friends Close..."? You know, the one that is a total Shout-Out to the finale of Scarface (1983)?
Big Lipped Alligator Moment: "Hit The Courier" has you attack a syndicate to steal some printing plates so Tommy can set up his own. The odd part is that the syndicate is made up entirely of women, and that this detail is never commented on at any point.
The free aim on the PC port turns the assault rifles, M-60 and minigun into this. Without the need to manually aim, you can hit enemies at sniper distances with ease. It also makes shooting drivers out of their cars a breeze.
The helicopter is this for missions. As soon as you can access one, you can bypass a lot of problems that were specifically set up to hound people in cars. With the exception of missions that force you into vehicles, taking a helicopter is always a better choice than driving.
Good Bad Bugs: In rare instances, a glitch may occur within your save file that gives you unlimited ammo for this gun, which can make breezing through enemy laden levels a cakewalk.
The SPAZ-12 Auto-Shotgun is no slouch either; It is able to empty its 7-round magazine in just over 1000 miliseconds allowing one to mow down a group of people, or detonate a non-bullet-proof car in one magazine or even less. It isn't as versatile as the aforementioned riffle-class weapons, but damn it's still deadly.
Ricardo Diaz crosses this in the mission "Death Row", admitting to Lance Vance that it was he who killed Lance's brother and then sending Lance off to be tortured to death.
Sonny Forelli crossed this before the game's events. In the final mission, it is revealed that he set up the entire incident which landed Tommy into jail and no explanation why he did that is given, and after the entire drug deal went into a complete mess in the beginning, it is implied that Sonny set the deal to go to waste and wanted to have Tommy killed. This shows that he has no problem betraying his close friend and one of his most powerful man in his organization for no reason and shows no remorse for this. And it is likely that Sonny would have killed Tommy if he would have given the money he made from his empire's operations.
Lance Vance seems to really cross this when he allied with Sonny and tries to kill Tommy. He even shows no remorse when he tries to kill Tommy and you see that he does it with glee.
Nightmare Fuel: Tommy is generally frightening when he's mad. He's somewhat irrational and using violence at any time, and even he kills people with chainsaws without any problem. Also keep in mind why he was nicknamed "The Harwood Butcher''.
Scrappy Mechanic: The police spawning. In an effort to correct III's laughably easy to avoid police (once you got used to the game's quirks), they overdid it. It's next to impossible to lose even a two-star wanted level without a pay n' spray. This is because once you hit two stars, the cops continually spawn EVERYWHERE. ALL THE TIME. No matter how far away you get from those following you, no matter how inconceivably remote of an area you attempto hide in, they will show up. See the supercop glitch. SA and onward adjusted this, but it's still really hard to get away from even a two star level until IV.
Tear Jerker: After the final mission we see that Tommy is crushed that Lance betrayed him. Ken tries to comfort Tommy by saying he never liked the guy.
Ken is Tommy's ally for the entire game and the final cut-scene suggests that they were embarking on a 'beautiful business relationship' together. In San Andreas we learn that Tommy sent Ken to rehab. After he got out and was completely clean, Tommy refused to talk to Ken. Ken is obviously hurt by this and still has delusions about Tommy.
Ken: Isn't this exciting, Tommy? It's just like old times!
The race against Hilary. You have to race him in an (admittedly decent performance) sedan while he uses a supercharged muscle car. You can't steal a better car, assuming you could even find one, because the sedan is mission-critical. The VCPD try to arrest you, and only you, for street racing. Assuming you get ahead (or fall behind), Hilary actually drives even better because game mechanics only spawn NPC traffic in relation to your car (the road is functionally empty from his POV). Finally, there's a glitch on the bridge near the end of the track which can cause you to clip through and fall to your death. This one mission has singlehandedly spawned countless pages of text on Game FAQS consisting of nothing but every method and theory in the world to win it.
Right after you off Diaz and become the new boss, you have to go to the mall to smash store windows. The clock is set to five minutes... starting from your house! For reference, the mall is at the back end of the first island, and you start from the center island. A good driver with a fast car (which the house will provide) can get there within 1-2 minutes, leaving three minutes to kill everything in sight, but if you get bogged down you fail. There's a helicopter on the roof that can get you there even faster, but there's a chance that won't spawn, forcing some Save Scumming to get it.
"Death Row", which is easily the most hated mission next to racing Hilary. To explain, you now know that Diaz is the one that messed up your deal at the beginning of the game. Tommy is content to wait it out, but Lance, like an idiot, jumps the gun and gets himself captured. You have to rescue him before he's beaten to death. You have to do this starting at the Malibu, while Lance is being held at the dump on the other side of the map. His remaining health is your timer, and starts right away. Sound annoying yet? Good, because it gets worse. The dump is barricaded by mooks armed with automatic rifles and high-powered machine guns which will chew through even an armored Tommy or a helicopter if you do a flyover. They're positioned high up on cover to make killing them harder and more time-consuming. Once you rescue Lance, you have to get him to the hospital, which is when three sports cars with goons decide to chase you down. If you blow them up, a fourth comes along. It also respawns (albeit slowly). On top of all of that, there's literally no reward. You don't get paid jack for one of the hardest missions in the game. Perhaps to make up for it, the next mission gives you the most powerful assault rifle in the game and is practically a cakewalk unless you're criminally incompetent.
That goddamn pizza man killing level definitely counts.
The one wear you dress up as cops and set up explosives at the mall. You can only drive to the mission in a standard cop car, with all other traffic in the area also being cop cars, and RIGHT after you set the explosives off, and despite wearing cop uniforms YOU IMMEDIATELY gain a four star wanted level and everyone zeroes in on you, somehow. Since you presumably don't have a regular car and the pay n spray won't take a cop car, the point of the mission is to get back to the mansion from the other side of the island with a near full wanted level and survive. It's incredibly tough to do even in a fast, tough cop car. Did we mention this mission is only at the halfway point of the story mode?
One of the exploits to the mission is to manage to steal an FIB SUV (which is possible, if not also fairly difficult) at the mall. The pay n spray doesn't recognize it as a police vehicle and will "respray" it (it actually doesn't change colors), which will nullify your wanted level. The other is of course to try to steal a civilian car on the way to the mansion and then hit a pay n spray. This is also incredibly difficult, as VC is a near ghost town during the chase (intentional presumably) and getting out of the cop car into another one with a ton of cops right on you with out you or Vance dying or getting your tires shredded before you even get the car moving is also really hard.
And of course you can try to steal a helicopter from the scene also, but taking off before the helo takes too much damage is essentially luck, and then you have to avoid air-to-air fire all the way back to the mansion, and THEN get to the save circle from wherever you manage to land. Of course, if you're really good with flying, its a great opportunity to get a helo early by landing it on your helo pad and then rushing to the save circle before you're shredded by the cops (who will spawn right at the mansion, no matter how far ahead you flew of them).
The RC helicopter side mission. Remember when you blew up that building? Good. Because this mission is a slap in the face to that. The helicopter, in complete defiance of the perfectly manageable one you flew before, is so damn sensitive that you'll literally do flips if you press a directional key. Not press and hold, just press. At least it's a checkpoint mission and the time limit doesn't affect 100% Completion.
Melee weapon rampage events. Targets tend to appear ain groups, and being gang members they are armed. Sometimes with guns. This is especially bad with the chainsaw, since you can't run while they can.
Hilary also counts as this, not just for being a pain in the ass to recruit, but ultimately failing in his mission by getting killed mere minutes into the heist and rendering his tedious level completely pointless.