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.
Moral Event Horizon: 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.
Tear Jerker: Louise's death, especially when she tells Vic to make sure that her baby daughter is taken care of.
"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.
"High Wire". Picking up a few cargo containers of the backs of slow-moving trucks with a sky crane isn't too hard, even with the wonky helicopter controls. However, once you have to fly all the way over to the other island and pick up Diego's small, fast-moving car while he's being chased by armed bikers, those chopper controls will make you want to tear your hair out.
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.
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.