- Bill going full Ham and Cheese in universe over a dead rabbit. What makes it even funnier is how quickly Bill regains his composure, with a firm "Understood?" Even funnier: the lament of a dead rabbit is coming from a butcher.Bill: I want you to go out there, and I want you... to punish... the person who's responsible... (sob) For murdering this poor little rabbit! (pretends to cry, suddenly regains his composure) Understood?
- During the play as the crowd pelts the actor playing Lincoln with produce, if you look closely, you can see Bill takes the time to slam dunk a whole cabbage onto McGloin's head.
- P.T. Barnum's escaped elephant running through during the Draft Riots is also rather hilarious, especially due to the Irish gangs' reaction. One thought for certain seemed to have this going through their minds: "Has the world gone mad?" Especially (to me at least) that the Irish were thought to be mad for chaos and crazy for war (reference to Stephen the Irishman.
- When Monk is running for sheriff.Boss Tweed: (impressed) That man was right born for this.Amsterdam: He's killed 44 men, and laid low a couple hundred more.Boss Tweed: Is that right? We should have run him for Mayor.
- The Reverend's Double Take at two obvious crossdressing men among the ladies at the Reform Dance. One girl whispers before the Reverend sees him, "You shoulda shaved closer." Both men sweetly greet the Reverend, "Hello, Reverend." The holy man seems to react with resigned Sure, Let's Go with That.
- McGloin being smacked across the face by a bishop. Of course, he really deserved it. And right before that, McGloin exclaims "Father! Jesus!" while the bishop Looks Like Jesus, if on the big side.
- The part during the comical forcing of votes in this scene has Jimmy Spoils (an Irish-African) pulling a drunk union soldier out of a depressing pile of similar bunches next to the trash.Jimmy Spoils: Come on, you bastard, we need your vote.Union Drunkard: (pissed) Bastard!? I fought for you nigger! I lost an arm for you! (shows missing right arm stump)Jimmy Spoils: (pulls out a shank and points it at him ) Well, that's a start. Now come on! (grabs and drags him away).
- "That, my friends, is the minority vote." Dark humor considering the cir cumstances, but still.
- "Now that was bloody Shakespearean! You know who Shakespeare was? He's the fella who wrote the King James Bible!"
- In a darkly comic scene, two rival volunteer fire companies brawl out a territory dispute, ignoring the actual blaze. The two chiefs (including Boss Tweed) overlook the fight and have a heated discussion over whose land they're on.
- Truth in Television, as the standard practice of the time was for the insurance company holding the policy on the building to pay a bounty to the first volunteer fire company to get water on the fire — one company would often have a man sit on a barrel to cover the fire hydrant to prevent other companies from using it before their company arrived (which is where the term "plug ugly" came from.) This obvious recipe for corruption soon led to significant reforms in insurance laws (and abolition of the bounty payments), as well as independent volunteer companies giving way to modern professional and sworn volunteer fire departments. The New York City Fire Department was established following the Draft Riots of 1864.
- When Amsterdam introduces himself to Bill.Bill: What is your name?Amsterdam: Amsterdam, sir.Bill: Amsterdam? I'm New York.
- "The appearance of the law must be upheld. Especially while it's being broken."
Funny / Gangs of New York