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- Before hiring Niko for some jobs, Elizabeta warns him that she won't be as easy to work for as his previous boss Manny Escuala was. Niko disagrees. Why? "I won't have to listen to him talk!" Everybody has a good laugh over his quip, and chances are you'll be laughing along with them.
- When Elizabeta starts freaking out because she thinks the cops are on to her, Manny busts in with his camera crew, spewing obnoxious preaching at Elizabeta. She promptly pulls out a gun and shoots him in the face. Almost everyone playing through at this point will be rolling with laughter at this, since, well, it's Manny.
- This cutscene, also involving Manny (and his God-awful camera man).
- Most of the intros to Brucie's missions, which usually involves him being stupid and either hurting himself, or getting Niko to hurt (or threaten to hurt) him. Also, the intro to the mission where Niko has to pretend to be gay. Including the profile that Roman sets up for him. Seeing Niko's mugshot-worthy face with the phrase "I just want to be wrapped in strong arms" had this Troper in tears.
Niko: Brucie, I don't need to see your balls. I'm good.
- Despite being a hardened criminal and killer, Niko still makes the types of jokes a 12 year old would make regarding Brucie's balls. A notable one is when he calls Brucie to inform him he failed an Exotic Export mission.
Niko: Brucie, are your balls OK? You sounded real mad.
- Almost all of Niko and Packie's back and forths with a Bound and Gagged Gracie Ancelotti in the mission "Diamonds Are a Girl's Best Friend" are gold. Actually, almost any time Packie is involved in a mission, or even just in the car, with Niko, it's usually pretty hilarious.
Niko: Scratch my fuckin' balls, bitch!
- Niko and Packie have a lot of fun at her expense.
Niko: "Packie, my man. How are you and Gracie getting on?"
Packie: "Like a house on fire, ain't that right, Gracie?"
Gracie: (muffled through her gag) "You fucking bastards!"
Packie: "See, she was just telling me how much she loved me. What do ya think of Niko, Gracie?"
Gracie: "I fucking hate the both of you!"
Packie: "Gracie, watch your mouth. Niko is a good friend of mine. Don't say that about him."
Gracie: "Fuck you, fuck you, fuck you, fuck you!"
Packie: "Gracie, you're sweet. I know I'm too good for him, but sometimes a guy has got to hang out with lowlifes like Niko here. He's got his uses."
Gracie: "I'll give you some fucking uses!"
Packie: "That's right, he is definitely a bad influence on me."
- And version B if you failed the mission once:
Niko: "Gracie, it's been too long. We should hang out more often."
Gracie: "I'd rather see you hanging from a fucking tree!"
Packie: "Hands off my woman, Bellic. Gracie and me is in love. Gonna get hitched. White picket fence and all that shit."
Niko: "Packie, this is great. You've finally found a woman who will sit down and listen to your shit. Maybe you should bind and gag all the girls you meet?"
Packie: "That might be okay where you're from, Niko. But this is an enlightened society we live in. U S of fucking A."
Niko: "Real enlightened, real civilized. That's the impression I've got so far. An example to the rest of the world."
Packie: "You know you love it, Niko. Doesn't he Gracie?"
Niko: "Maybe Gracie ain't so different. You normally just shove so much coke up a girl's nose that she may as well be tied up."
Packie: "You're in a mood, ain't ya Niko? Is it finally beginning to sink in that my sister's chastity belt don't come off?"
Niko: "Fuck you!"
Packie: "Fuck you!"
Gracie: "Fuck the both of you!"
- Listening to the Tuff Gong radio station (you know, the reggae one) causes some pretty hilarious soundtrack dissonance. A high-speed cop chase underlaid with somebody singing mellowly about a girl who likes to party and have a good time, or Bob Marley's "Three Little Birds". Then you'll hear the host warning the listeners not to buy the Excelsior razor, saying that "you might cut off ya nose".
- Niko is chasing a couple of scared mooks in a car on a highway, driving in the wrong lane, hellbent on exacting righteous retribution... as Roman and Jacob comment on how they've never seen much of Alderney and how much it's unlike Liberty.
- Niko's summation of not-so-stable gangster Roy.
Niko: "He's a rat doing an impression of a man."
- Drug dealer Playboy X needs the main character Niko to kill someone who has been talking trash behind his back. His description is... unhelpful
Playboy X: Son ain't too diesel or nuthin', but he a regular lookin dude, knowwhatimean? And he don't flash his guac too much, but you can see it in his eye, he a hustler.
PBX: Homie ain't too brollic, but he ain't scrawny neither, and he beats down on him a little you dig? I mean, he ain't too bummy, but he grimy, too.
Niko: ...so he's the average one?
PBX: Look, he brown skinned B, motherfucker be rockin' baggy clothes, all that, jewels and he stay fresh with the clean sneakers, knowwhatimean? But sometimes a bandanna.
Niko:: Look. I need more than that to go on.
PBX:: Jesus. Here, take this [camera phone], head down there, take a photo, send it to me, and I'll point out which one of them motherfuckers it is.
- Niko is looking for the guy who sold his army unit out. His first lead is some Florian Cravic. Ray finally gets a lead on him, and he takes Roman on his little revenge quest... Only to find that not only he's not the guy Niko's after, but he also changed a lot after going to America, changing his name to Bernie Crane, becoming a lifestyle instructor (as he says) and having an affair with... the Deputy Mayor, Bryce Dawkins. It's funny because you get Flamboyant Gay when you expect some kind of shady, dirty-looking dude as a traitor.
- The cutscene after the very first level. While a lot of it is funny, CMOF has to go to when Niko starts giving an introspective, very serious narration on his time in Serbian Army, which sounds like it could have come right out of the mouth of Solid Snake. Roman's response? He falls asleep.
- In the cutscene for the mission "Crime and Punishment", Mikhail's reaction to Andrei's...enhanced interrogation techniques is priceless.
Mikhail: (Deadpan) Good lord...what are you doing?
- In "Do You Have Protection?", Dimitri lets Niko buy himself a new weapon, on Mikhail Faustin's account:
Dimitri: I want to buy you a present.
Niko: Will you wrap it up and put a pretty bow on it?
Dimitri: Screw you.