Crowning Moment of Funny: When you fail the mission "In the Air Tonight", you can hear Phil'sBig "NO!" and a funnier version of the mission failed caption that says that "Phil really felt something in the air tonight".
Harsher in Hindsight: "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.
"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 Lance, who is riding a motorcycle and seems to enjoy 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 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 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 Louise, the woman you went through all this hell to save, is dead.What fun!
This is subverted to some extent, however, if you took the time to complete the fireman missions, which make the boss' weapon completely useless.
Ok, let's talk about High Wire now. You're basically pulling an Escort Mission 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 Fake Difficulty as you're attempting to drive down and collect the car. The 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 Difficulty Spike 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!
That One Sidequest: 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.
Louise herself tends to fall into this. Thanks in large part to her status as a Damsel Scrappy.
The Woobie: 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.
Iron Woobie: Victor Vance. Unlike all the other playable characters of the series (including 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 idiot, Jerk Ass, Man Child and a crazy for the money without seeing the consequences.