* CrowningMomentOfFunny: When you fail the mission "In the Air Tonight", you can hear [[PhilCollins Phil's]] BigNo and a funnier version of the mission failed caption that says that "Phil really felt something in the air tonight".
** When you pass the mission "Domo Arigato Domestoboto", Armando shoots his robot, Domestobot (which looks like {{Nintendo}}'s VideoGame/RoboticOperatingBuddy {{pastiche}}), unaware that it was controlled by Vic.
-->'''Armando''': Domestobot! [[YouHaveFailedMe You lousy piece of crap, you've ruined me!]]
-->'''Domestobot''': [[ComicallyMissingThePoint Do you require a light?]]
** During "Unfriendly Competition":
-->'''Dealer''': This is a private party, pal.
-->'''[[DeadpanSnarker Victor]]''': Yeah, well this is a public execution!
-->'''Dealer''': Holy shit! Get him, girls! ''(runs away while all [[ThisIsGonnaSuck his girls aim their guns at Vic]])''
-->'''Victor''': ...Motherfucker!
** The whole opening cutscene of "Turn on, Tune in, Bug out".
-->'''Lance''': (whispering) Keep your voice down!
-->'''Victor''': No. You can barely tie your own shoelaces and ''you tellin' me how to behave?''
-->'''Lance''': [[SuddenlyShouting WILL YOU SHUT UP, YOU STUPID GORILLA?!]] [[NoIndoorVoice THE PLACE IS BUGGED! THE DEA IS ONTO US!]] HAPPY NOW?!
** In one of the earlier missions, "Cholo Victory", there's Phil Cassidy's EpicFail when he tries to drive his pickup truck.
-->'''Phil:''' Let's go, YEEEE-HAAAAAR!!
-->''(Phil crashes into a wall)''
-->'''Victor:''' Maybe ''I'' should drive, man.
-->'''Phil:''' Damn stick shift!
* CrowningMusicOfAwesome: The entire soundtrack.
* FridgeLogic: Why is Barry Mickelthwaite PhilCollins' manager? What happened to [[http://en.wikipedia.org/wiki/Tony_Smith_(manager) Tony Smith]]? Admittedly, this may only be a FridgeLogic moment for Collins and/or Music/{{Genesis}} fans. Given Collins's [[PromotedFanboy personal involvement in this game]], this was almost certainly a plot necessity/plot device.
* HarsherInHindsight: "The Bum Deal", aka the White Stallionz mission, involves the Vance brothers having a shootout with a gang of homosexual bikers in a bar. Then in 2016 (ten years after VCS was released), a mass shooting occurred at a gay nightclub in Orlando, Florida.
* MoralEventHorizon: Marty Jay Williams crosses the line when he kidnaps his own wife Louise and tries to turn her into a prostitute.
** Jerry Martinez crosses this when he kidnaps, rapes and intentionally injures Louise.
** Armando Mendez absolutely crosses this when kidnaps and kills Louise.
* TearJerker: [[spoiler: Louise's death, especially when she tells Vic to make sure that her baby daughter is taken care of.]]
* ThatOneLevel:
** "Turn On, Tune In, Bug Out". The level involves destroying six antennae on the roofs of Vice City's police stations with a rocket launcher before the DEA can gather incriminating evidence on the Vance Brothers. For starters, you're on a time limit, and every time you destroy an antenna, your wanted level rises by one star. This wouldn't be so bad if Pay-and-Sprays worked normally on the mission, but instead, they only remove the player's wanted level temporarily, restoring it to whatever it was previously once the player nears an antenna. On top of all this, once the final antenna is destroyed, the player must lose their wanted level without dying - a tall order at 5 stars, where FBI teams with high-powered automatic weapons and fast-moving vehicles ''litter'' the streets and traffic ceases to spawn. The mission is ''slightly'' easier if you use a helicopter to go from antenna to antenna, but that still leaves the escape to the hands of fate, as losing a wanted level ''requires'' the use of a non-police land vehicle.
** One of the final missions, "Light My Pyre". The mission begins with a highly annoying car chase that wouldn't be so bad, except you have to escort [[TheLoad Lance]], who is riding a motorcycle and seems to enjoy [[AnnoyingVideoGameHelper getting in your way (sometimes, even in your line of fire) and getting himself killed, which is a Game Over.]] Then, you have to fight through a small army of heavily armed, respawning goons to get around the back of a building and through a door. THEN, you have to fight [[spoiler: Armando Mendez]], who is wielding a flamethrower. If that weren't enough, you're forced to fight him in a disorienting top-down perspective -- not to mention, his goons storm in and fight you, as if a man setting you on fire with a flamethrower wasn't enough. (This part is made almost laughably easy [[GameBreaker if you have a minigun with you]], but if you don't...) And if you die? Back to the beginning. And if you do finish it? You find that [[spoiler: Louise, the woman you went through all this hell to save, is dead.]] [[SarcasmMode What fun!]]
*** This is subverted to some extent, however, if you took the time to [[spoiler: complete the fireman missions, which make the boss' weapon completely useless]].
** Ok, let's talk about High Wire now. You're basically pulling an EscortMission with cocaine crates using a huge magnet on the bottom of a helicopter for the first two thirds, and it seems like everything's normal, but then you hear this: "HELP! THE BIKERS ARE ON ME, I CAN'T GET THEM OFF!" and you must go after a moving car that has bikers constantly shooting at it with Sub-Machine Guns, making it move around erratically, in turn causing FakeDifficulty as you're attempting to drive down and collect the car. The [[SarcasmMode BEST PART of this]], you may ask? The car has an HP meter of sorts, and if the bikers hit it enough times(read:about 15 or so streams of bullets), it'll blow up and you'll have to start over from THE VERY BEGINNING OF THE MISSION. Have fun.
** If you thought picking up cargo containers and a gang car with a helicopter in "High Wire" was bad, you haven't seen "White Lies" yet. You have to follow Lance's helicopter in a hovercraft and collect cocaine that drops from his helicopter. This is easier said than done, considering that the hovercraft handles horribly.
** "Jive Drive", which must wholly be blamed on the PSP's lack of a second analog stick. After a hair-raising drive to an abandoned lot, being shot at all the way there (thankfully this isn't terrible as your car has decent armor), you must survive a gauntlet of fire on you and your brother. Lance is useless with a gun and if he dies, WHOOPS, start over. The fact that you can't get a clear look around you with the PSP's limited control scheme is the main reason you will fail this mission.
** "Unfriendly Competition" is a MAJOR DifficultySpike compared to missions before it, it's not too hard until you get to the swimming pool, which is absolutely crawling with enemies and has very little cover, making it insanely hard to kill all the enemies without getting killed yourself, and if you somehow survive you have to chase down and kill the last two guys using a quad-bike, which is very awkward to control and it's hard to drive and aim at the enemies at the same time.
** The ATV race in "When Funday Comes" is anything BUT fun. To better elaborate, you have to win a quadbike race around the trailer park against some rednecks. Which SHOULD be easy except that the quadbike handles fucking horribly!
* ThatOneSidequest: Vigilante. While the earlier levels are acceptable, the later levels have enemies that can tear Vic to shreds if the player doesn't plan ahead or exploit the AI.
* TheScrappy
** Lance, [[TheLoad BIG TIME]]. Even more so than in ''Vice City''.
** Marty J. Williams is even more disliked by many fans due to how he abuses Louise and even threatens to ''beat down their baby child''.
** Louise herself tends to fall into this. Thanks in large part to her status as a DamselScrappy.
* TheWoobie: Louise. She did not finish high school, her ex-husband abused her verbally (and probably physically), was kidnapped twice (and allegedly raped and tortured) by Jerry Martinez and Armando Mendez, and finally being killed by Armando.
** IronWoobie: Victor Vance. Unlike all the other playable characters of the series (including [[VideoGame/GrandTheftAutoSanAndreas CJ]], who has been considered have more "moral" than most), Victor Vance in the background does not like to be a drug dealer or kill people, he just feels compelled to to. Adding to this, his mother is a drug addict, and his brother an [[TooDumbToLive idiot]], JerkAss, ManChild and a crazy for the money without seeing the consequences.
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