The look on Lucky Luciano's face when Arnold Rothstein tells him that he's sleeping with Jimmy's mother, not his wife.
Rothstein's snarking in that scene is pretty funny, too - "I've got a crystal ball, Charlie, and you're missing your trousers."
When Agent Van Alden is interrogating a wounded Jewish gangster in a dentist's office, the man replies in Yiddish. The middle-aged woman nearby reacts to it, and Van Alden demands she translate:
Woman: I can't...
Dentist: Mrs. Fishbaum!
Van Alden: Word for word. This is a federal invastigation.
Woman: He said you should fuck your grandmother... with your faggot penis!
Then topped when Van Alden's partner Agent Sebso corrects her: the gangster specifically said "little faggot penis."
The fact that he bluffed his way into getting the guy out of Atlantic city by making up a non-existent type of warrant and paying some homeless guys to pose as his backup, and then when it looks like the guy's going to die he just bursts into a dentist's office and demands the dentist give him a double-shot of cocaine in the mouth to wake him up.
Rothstein, on the topic of the D'Alessio brothers:
You know what the nice thing about the Bronx Zoo is, Charlie? There are bars between you and the monkeys.
"That imbecile is going to be the next President of the United States!"
The maid's explanation to why she chose to poison the Commodore instead of outright killing him. "Because if I had used a shotgun, I'd have to clean up the mess myself."
Perhaps one of the darkest funnies in recent television, near the end of the first season when Chalky has taken two of the D'Alessio brothers prisoner. One starts getting lippy to Nucky and Jimmy...
Mook: Fuckin tough guy huh, gonna shoot me for mouthing off?
Jimmy: Well, I wasn't going to but now you kinda talked me into it. [BANG]
As well as the look on Meyer Lansky's face. If his hands weren't tied, he would have facepalmed.
Van Alden's Oh, Crap reaction when Lucy walks into his office which gets even worse when she reveals she's pregnant.
In "Ourselves, Alone", Lansky and Luciano's tandem Oh, Crap reactions to Bugsy telling them that Rothstein's outside waiting for them.
And then later in the scene, Rothstein one-ups them by volunteering them to be muscle on a liquor delivery in lieu of allowing Joe Masseria to kill them. The subsequent stunned look from Luciano and Face Palm from Lansky are perfect.
The Commodore, abed after suffering a recent stroke, labors to speak to Eli, who leans in closer only for the old man—who can barely form words—to loudly call him a “cockfuck.”
Van Alden and his wife walking in on two agents wrestling in the office.
Mrs. Van Alden looks very turned on watching her husband bust a restaurant that's selling liquor. Cut to a bed hammering against the wall...and zoom out to reveal Van Alden is showing her the mattress is busted.
Made all the funnier/more ironic by the fact that Nucky has to be a maximum of two generations removed from the Emerald Isle himself.
A really dark one is the "...seriously?" look on Jimmy's face when Manny Horvitz says he can't kill his associate, Herman for conspiring with Nucky . . . because he's injured. Manny's a kosher butcher, of course.
It's also kind of funny (also in a dark sense) in that part of Jimmy's reaction is to the effect of "Wow, so this is how crazy other people think I am."
Plus his "What the fuck?" when Angela's girlfriend rather than Jimmy falls out of the bathroom dead. It's like he's wondering if he got the wrong house.
Nucky upon hearing Margaret's son crying after she slapped him: "You were just praying!"
When Nucky and Teddy visit New York to consult Rothstein's lawyer, Bill Fallon, Teddy spies a baseball in Fallon's office signed by Ty Cobb. Fallon makes a big show of giving it to him. As Teddy goes out of the room to let the men conduct their business, Fallon opens his desk drawer to reveal a drawerful of signed Ty Cobb baseballs. The smirk on Rothstein's face and the raised eyebrow from Nucky just make the scene.
Arnold Rothstein has to have the classiest way of calling bullshit on someone in history:
Luciano: Word is, [Nucky]'s got a beef with his brother.
Rothstein: I would have thought James Darmody.
Luciano: Nah, Darmody ain't got it in him.
Rothstein: Pillow talk, Charlie?
Luciano: What, his mother? I'm through with that.
Rothstein: (nods, then sniffs and has a disgusted expression on his face)
Lansky: What's the matter?
Rothstein: Manure. But what can you expect when you conduct your business in a stable?
Torrio's What an Idiot reaction to Al not getting his "Romulus and Remus" joke.
Lucky, Lansky and Capone telling Doyle that they are cheating him out of his part of their previous deal, then Capone slapping Doyle while laughing his ass off.
And then Doyle tries to get back his money by recruiting Van Alden for a fake federal raid against them:
Doyle: I put this whole operation together, and what do I receive? A poke up my ass.
Van Alden (deadly serious): Painful.
This exchange from the season two finale:
Nucky: Et tu, Eli?
Nucky: Shakespeare. Julius Caesar.
Eli: There was a character named Eli?
One small funny moment from an otherwise very dark scene - Jimmy's death. Jimmy asks Nucky who's going to do it. "Manny? Eli? (looks to Owen for a couple of seconds) ...You?"
Richard makes an attempt to tell Tommy about his dead mother when Gillan intrudes and asks what he was talking about. After a few seconds of muttering, Richard replies with "The war" in a manner where even he isn't convinced that Gillan would believe him. It's almost hilarious that despite his times with Jimmy, Richard is still unable to tell a lie.
Rosetti's entire "The Reason You Suck" Speech to the other businessmen, particularly the prelude when Nucky arrives "Look, another mummy" and the line "You smug kike midget, creeping around like a fucking dentist with the ether" to Rothstein, who replies with his trademark smile to the rant.
In addition to being a Moment Of Awesome, Van Alden coming into a florist to sell irons and finding himself accidentally becoming a temporary mob enforcer is brilliant, as is the mobster's "I can't believe that worked" reaction after the situation gets defused. The funniest thing is that Van Alden doesn't actually do anything except stand still, look impassively intimidating, and say as little as possible (ie exactly what he always does).
Rosetti's Blatant Lies at Tabor Heights during the "no fuel here" scene, Owen can't keep a straight face.
Gyp: I'm D.L. Collingsworth. Proprietor. Yeah, we go way back. Slept with George Washington and everything.
The entire scene of Mickey picking up Eli from prison. Particularly Eli asking the same question as everyone in the audience: "How the fuck are you still alive?"
The sheer irony value of Van Alden being arrested in a speakeasy raid, and bribing a cop to let him go.
Richard marching Mickey Doyle out of his apartment at gunpoint, in his underwear, gets even funnier when Richard takes him to Nucky:
Mickey: I didn't kill Manny Horvitz!
Richard: He's telling the truth.
Nucky: How do you know?
Richard: How do you think?
A psychotically awkward moment when Gyp seems about to explode in a fit of rage because he feels he's been compared to a monkey. Gyp then starts mimicking monkey guttural sounds to reveal that he's just trolling, much like Tommy DeVito in Goodfellas.
Owen attempting to write the Italian phrase for "good luck".
A nun's Bowdlerization of the hospital's pre-natal care seminars, followed by Margaret coyly suggesting that maybe she could use a Kotex.
Nucky paying off Agent Zowicki, and telling him to "go buy a personality".
Gyp Rosetti's Easter dinner, where the violent psychopath is completely cowed by his female relatives. What ices the cake is when Tonino attempts to leave Rosetti alone with them and he throws him a terrified look, both threatening and supplicating.
Nucky's juggling act.
When Eddie Cantor is visited by Nucky's thugs, the poor guy worsens it by referring to Chalky as "Milky".
Nucky finally paying the price for his boozing... a 5$ fine he just shrugs off pulling out a wad of bills and asking the bailiff if he can break a 100.
In "The Pony", Eddie barges into Nucky's office where Eli and Owen are present with news of Jimmy's death. Nucky immediately dismisses it as speculation until Eddie reveals that it's in the newspaper as a drowning accident. The quick exchange of "WTF?!" between Nucky, Eli, and Owen is just hilarious.
Esther Randolph's answer to Nucky's asking what does she do for fun: "I run naked through the pages of the United States criminal code."
The arrest of George Remus. Remus is chased around his house by the Feds, until Remus slips and falls on his ass. And then Randolph indulges herself in some Remus-speak.
Remus: Remus has paid! Remus has kept recipts!
Randolph: Then Randolph would like to see them.
Tommy Darmody is drawing a typical kid's picture, and has to explain it to one of Gillian's hookers. Richard gets it right away:
A whole beach full of people going nuts over whiskey bottles washing up on shore, having fallen off one of Gyp's boats. A guy dressed as King Neptune for the show they came for tries to keep their attention for a few seconds, then runs over to snag a few himself.
The quick degradation of Gillian's 'classy' brothel after Gyp takes over it, ending with her hitting a gangster with a broom so he'll stop fornicating in the middle of the reception room. She totally looks like an old lady trying to throw some street dogs out of her yard!
After Chalky's and Capone's men spend an episode fighting each other, they work together to slaughter the men Masseria sent to Gyp, and Capone simply says "Glad I got that out of my system" and they part on good terms.
"That guy with the mask. Who the fuck was that?" It's a little amusing when you consider that most of Gyp Rosetti's men killed by Richard had no idea who he was or why he attacked them.
After being bombarded with questions concerning the gang wars and Nucky Thompson's involvement, Mayor Bader replies: "Let's get something straight. Nucky Thompson doesn't run this city! I do!" Cue reporters bursting into laughter.
Masseria's losing his sardonic grin and showing his annoyance about Rothstein "still taking dinner in Times Square", and his condescending dominance over Rosetti in general, e.g. casually patting Gyp on the cheek and setting his clock to remind Gyp his time is running out.
Nucky and Eli's "Oh, for god's sake!" faces upon seeing Dickie's mutilated corpse.
Al Capone's obsession with a newspaper article spelling his name wrong.
Likewise, Al and his brother Frank, two grown men, wrestling on the floor of their home like kids. Their other brother Ralph spurs them on until Mama Capone comes in to break things up.
Van Alden is going door to door, working for Dean O'Banion who is a gangster and a florist. At one place, the female resident just had a baby. Van Alden delivers flowers, and he tells her: "Mr. O’Banion sends his congratulations." Another place just lost a member of the family. Van Alden delivers flowers and tells the man answering the door: "Mr. O’Banion offers his condolences." At the third place, a man opens the door. Van Alden punches him and says (at the same, monotone tone he was using previously): "Mr. O’Banion wants his money."
Eddie's over the top Badass Boast on Nucky's behalf when Ed Bader doesn't show him the proper respect.
Eddie: Mr. Thompson is part of everything, he is in the sky and sea... (Nucky gives him a bewildered look) He is in the dreams of children at night. He is all that there is... forever.
Willie Thompson, attempting to impress a college girl, tries to persuade Mickey Doyle to sell him booze. Doyle laughs him off, and Willie steals a crate...only to get caught. Doyle chews him out and even slaps him, then realizes exactly who's son he just hit...then attempts to laugh it off, and even tells him to the take the booze.
It seemed more like he was taking pity on the kid and deciding to just let him have the stuff just once.
The day after cancelling a deal with Florida land baron August Tucker that Bill McCoy had brokered (and that leaves Tucker furious with McCoy), Nucky phones McCoy to tell him that he has reconsidered and will buy Tucker's land after all. The distressed McCoy hangs up and sits on a chair next to Tucker's body, lying on the floor with a machete sunk in his head.
After van Alden/"Mueller" delivers the flowers to the hospital, the Capones take exception to their rather bedraggled state:
Van Alden: Mr. O'Banion meant no disrespect.
Al Capone: The man's sick. How else is he supposed to take it, huh?
*Jake is unconcernedly eating his lunch*
The Capones and van Alden have come across a possible easy heist:
Van Alden: It may just be a bread truck.
Al Capone: I may be kinda hungry.
Van Alden telling Capone that he has a sense of humor. For someone who watched the show from the beginning, this is hilarious.
Meyer: One day on my way to school, I got stopped by a gang of older boys. The leader said he wanted my lunch money. I told him to go fuck himself. He laughed, said he'd beat it out of me, so I spit in his face. He did beat me, they all did, and they took my money. Next day, same thing. I spit in his face and then we fought. The third day, the kid asked me to join his gang. The kid was Charlie Luciano, and that's how we teamed up.
Eddie has been arrested, and has been asked about his pistol:
Richard and Julia go to get a marriage license, where the sign that hunting licenses are given in the same office is funny enough. Then Julia asks if he's nervous, and Richard replies "It's just a hunting license."
Nucky and Rothstein's entire discussion about having Mickey killed. "I know ten guys who'd kill Mickey for free."
Nucky: So what are you waiting for? Kill him.
Rothstein: At the very least, I wanted to extend you the courtesy of obtaining your permission.
Sigrid keeps nagging Van Alden (who is under a lot of pressure) about their Sears and Roebuck house being faulty. Eventually, he has enough, and when she asks him whether he called Sears and Roebuck, he responds:
Van Alden: Yes, yes, I did. I spoke to Mr. Roebuck himself. He apologized profusely and told me he would send a dozen of his top men over immediately to remedy the situation to our total satisfaction.
Mickey asks if Nucky has seen The Thief of Baghdad, to which Nucky asks "You have time to go to the pictures?" Mickey sputters for a few seconds about not having it, then just leaves.
Margaret (in her new job assisting at the stock market) is talking to Rothstein alone about helping him take advantage of her boss' attempt to con him, and when she mentions she's nervous, Rothstein tells her not to worry, because he's a married man. She exclaims "You must be joking!" in quite a loud voice. Rothstein assures her he is joking, but still seems rather taken aback by the vehemence of her reaction. While we've seen him get angry on a few rare occasions, this is the first time he's looked honestly bemused.
Chalky's new "friend" holding him at gunpoint and demanding to know how telephones work.
Mr. Bennett's suicide is quite morbidly hilarious, ranting and raving about a Mickey Mouse short and screaming "Everything's going to be fine!" just before shooting himself.
Eli's troubles with an old woman's feathered hat in an elevator.
After Eli's temper causes a robbery to be rather more violent than necessary, Van Alden shouts "Why must it always be pandemonium?"
Mickey's back to his metaphor failure:
Nucky: They told the Indians they could keep Oklahoma.
Mickey: How'd they get involved in this?
Mickey refilling a bottle of the "good stuff" after Nucky refuses the drinks he offered, because Kennedy Sr. wanted a soda.
Mickey:(to the bartender) Whoa, Madame Curie. Give me that!
Nucky's reaction when he thinks that Margaret was Rothstein's mistress.
Margaret:(annoyed) Not that! Why does everyone assume...
After Luciano identifies Van Alden as a federal agent, Al Capone interrogates him at gunpoint. Van Alden responds in his usual deadpan mannner.
Al: You think I'm stupid?
Van Alden: No successful man is stupid.
Al: Are you successful?
Van Alden: Not really.
Van Alden: I get the feeling my boss doesn't like me.
Eli and June's dinner with Van Alden and Sigrid is a squirm-inducing joy from start to finish, with Sigrid's utter frustration and resentment at what her life has become boiling over at the most inconvenient time.
Van Alden on his son playing the flute: "Chester, that would sound better much further away."
Van Alden:(to Eli) I, for one, refuse to be ruled by fear.
Van Alden:(jumping to his feet) Coming, dear!
Just when Sigrid reveals that she and Eli had sex, the police arrive and take Van Alden and Eli into custody. Eli tries to explain himself:
Eli: The event you're thinking about that was an accident. Plain and simple.
Van Alden: You mean like a streetcar hitting a horse? A man getting his head crushed in a metal press? A gas explosion in which bystanders are literally torn limb from limb? That's what your having sexual relations with my wife was like?
Eli: Look I don't know about you, but my life is a fucking shipwreck.
Van Alden: Well, land ho.
After Van Alden and Eli are caught trying to take Capone's ledger, they claim they were trying to rob him.
D'Angelo: How did you geniuses get that idea?
Van Alden: My wife.
D'Angelo: Your wife told you to rob Al Capone?
Van Alden: We're having trouble at home.
Eli:(raises his finger) I can vouch for that.
Capone believes that Van Alden is an undercover federal agent... and that he has been one for the 8 years or so he has known him:
Capone: All this time? That shit, with the irons...?
The Pity the Kidnapper plot with Benny Siegel, including Lucky assuming he's fooling around with a girl and hanging up on the ransom call, and Mickey discovering someone even more annoying than him.
This includes poor Talia, who gets shoved to one side three times during Siegel's kidnapping.
Eli getting a package from Nucky. In it is a ton of money plus a shaving brush and razor blade. Eli staring at the brush and blade quizzically just caps it off.