- There is a darkly hilarious Soundtrack Dissonance when driving around in a car with the radio playing. It is entirely possible to plow through a patrol of heavily armed pirates, flip the truck trying to avoid a tree, roll several times, smash the hell out of your ride, and explode, all framed to music that sounds like it was ripped from Spongebob Squarepants.
- When you meet "the man in white":
Willis: You have ten seconds to tell me who you are before I remotely detonate the C4 under the table and this whole place explodes like a pop bottle.
- Agent Willis is so bizarrely, nonsensically jingoistic it wraps around into pure comedy candy.
- He also happens to be the one who writes the Database entries. Hence his own entry simply reads "That information is classified. You didn't think it would be that easy, did you?"
- As another example of a database entry, the one on hang gliders:
"Hang gliders are for people who look at the airplanes and think, "What's the point of that engine?" Or for people who scream as they're sucked into an engine, "Why did I go hang gliding?!"
- The one about the ziplines is a good example too, especially this line:
"One day, one of those is going to lead straight into a volcano, mark my words."
- Some of the unexpected reactions from the enemy AI: for example, it's not unusual for an animal as small as a dog to aggro a Molotov enemy who then proceeds to throw a bottle and set half the outpost on fire.
- In conjunction with the similar entry in the CMOA, the juxtaposition of rocking out to this while marijuana plants go up in flame and sniping/blasting/torching the guards is darkly amusing. Especially when Jason starts getting dopey from the fumes...
- Sam's response after Jason successfully infiltrated the mercenaries is hilarious:
Sam: (hushed) You ready?
- Near the end, when Riley is trying to fly the helicopter while Jason is shooting:
Riley: I can't do this! We're so gonna die!
- Michael Mando and Christopher Mintz-Plasse made a series of videos showing Vaas torturing Christopher on the beach. The entire series is some of the most hilarious Vaas content you'll find, especially when he uses the firecrackers, freaks out when he thinks Chris may have died, and starts thinking of ways to revive him like a surgeon in a bad medical drama.
Vaas: Carlos! Get some water! Bring the batteries! The spiders! Everything!
Vaas: Bambi! I'm sorry I shot your mamma, Bambi! BAMBI!
- Predatory animals are hostile to all humans. Nothing quite as hilarious as watching a pirate patrol shooting at you suddenly get torn apart by a single hungry tiger.
- Sure, it's Black Comedy, but Buck's first conversation with Jason.
Buck: Keith? Is that his name, Keith? See, he told me his name was (imitates trying to scream through a gag).
- Hell, Buck in general is pretty amusing. He's consistently funny enough to be likeable if you forget that he's raping one of your friends while you're off fetching his knife.
- This line, after Jason is told to meet Buck:
- Random pirate chatter can lead to this.
Jason: (shoots him)
Pirate: God... this... heat...
Pirate: Hey... If you could choose, how would you like to die?
Pirate: In a really big fucking explosion.
Jason: (C4 or grenades them)
- Every once in awhile, you'll run across a pirate complaining about how much it burns when he urinates. It breaks up the monotony of stabbing their friends with a machete without any of them realizing it.
- Some of the Story Quest-givers you meet are very, uh, forthright.
Quest-giver: You look like a man who wants to shoot something, but has nothing to shoot!
Jason: ...That has got to be the strangest "hello" I've ever heard.
- During the escape from the hotel, while Liza is driving.
Jason: Drive faster!
Liza: I'm offroad! I can't go any faster!
Jason: Says who? The cops?!
- Vaas' first words.
- His whole introduction is great
Vass: YOU FUCKING DEAF? RUN FORREST, RUN! (proceeds to start shooting at you)
- The "Letters of the Lost" are letters that were written by members of the Japanese army during WWII. They usually show how they lost their heads (it's implied the island's influence slowly drove them crazy) specially Private Tadao, who sabotaged the radios of the island to stop anyone from knowing what happened to their families. All that goes out the window when you find Hurk's letters. These tell the story of how he trained a gray macaque monkey (that he named Gilbert) to throw grenades and that he's a menace but he gets sidetracked talking about a cheerleader of his school that turned into a pornstar, how Gilbert is not "throw crap at you"-evil but rather "rub crap in your face"-evil and lampshading that there are dozens of Japanese letters on the island.