- The meal with Hanna is so surreal that it becomes hilarious. It's hard to say what makes the better punchline: Hanna shamelessly defining what he and the Wall Street brokers do as a racket, prescribing Jordan to jerk off at least twice a day instead of 4 times a week ("rookie numbers"), introducing cocaine as the key of success, or his absurd humming + chest thumping. And everything is delivered completely straight by Matthew McConaughey.
- The chest thumping becomes even more hilarious if you're aware that this is something McConaughey actually does to psyche himself up for a role which they decided to work into the film.
- Jordan takes a job at a very small firm in the wake of his first firm's closing after Black Monday. His first conversation with his new boss has him saying that if Jordan sells 10,000 shares, he'll suck his dick... and that he hopes that it happens. Very quickly, Jordan does his first cold call there: his tactics manage to sell 4,000 and get the entire rest of the building staring at him."...How'd you fuckin' do that?''
- Donnie and Jordan's conversation about how Donnie married his cousin, which quickly Crosses the Line Twice when Donnie says what he'd do if they had a mentally disabled child.
- Donnie's line of "I'm not going to let just anyone fuck my cousin."
- Donnie and Jordan smoking crack and then running down the street high as kites."Fuckin' smoke crack with me, bro!"
- Jordan demoing his script to the staff in the early stages of Stratton Oakmont: he constantly pantomimes sex motions during the entire call, while everybody else watches and laughs.
- Donnie's reaction to seeing Naomi for the first time.
- "On a daily basis I consume enough drugs to sedate Manhattan, Long Island, and Queens for a month. I take Quaaludes 10-15 times a day for my 'back pain,' Adderall to stay focused, Xanax to take the edge off, pot to mellow me out, cocaine to wake me back up again, and morphine... Well, because it's awesome."
- Jordan and Co. talking over just what they can get away with regarding throwing little people at targets.
- Jordan's dad Max confronting him and the others over how much money the company spent the previous month:Max: Jordy, look what you've got here! Look at this! $26,000 for one fucking dinner!
Jordan: OK, no, no, this can be explained. Dad, we had clients, Pfizer clients. Champagne.
Rugrat: The porterhouse from Argentina.
Jordan: Expensive champagne and the wine. We had to buy champagne. [to Donnie] And you ordered all the fuckin' sides. Tell him about the sides.
Donnie: I ordered the sides, so—
Max: Sides?! $26,000 worth of sides?! What are these sides? They cure cancer?
Donnie: The sides did cure cancer, that's the problem, that's why they were so expensive.
Jordan: [bursting into laughter] Shut the fuck up.
Donnie: I'm serious, I'm—
- Later on in the conversation when he points out how much they spent on prostitutes:
- Nicholas, a gay butler Noami hired, abusing his position by organizing a gay sex party at the couple's penthouse appartment while the couple is out of town. His immediate reaction after Noami unexpectedly catches him in the act, in stark contrast to his professionalism while on the job, tops this scene.Nicholas: (Stops performing fellatio in surprise) Oh, hey. Is it Wednesday already? Uhhh... (Turns to other guests) WHAT THE FUCK!? THAT IS FUCKED UP!
- Afterward, Jordan and his crew interrogate Nicholas about money and other stuff that went missing after that gay party. When Nicholas gets defensive and accuses Jordan and Donnie gay-bashing, Chester just calmly gets up and starts beating the crap out of Nicholas. Donnie, standing close enough to get sprayed with blood, gets so horrified he has to run out onto the balcony to throw up.
- Jordan's stag do, which basically starts as an orgy on a flight to Vegas, turning into an even bigger orgy at the hotel. The final bill comes to $2 million including the remodelling required for the entire 28th floor of the hotel.
- On the plane, the camera shows off various parts of the orgy...including two guys who are sharing a drink and having a nice conversation in the middle of this debauchery. And in the background you can see two other guys sitting by themselves and minding their own business.
- Jordan and Naomi's fight after he mutters Venice in his sleep. She repeatedly throws water in Jordan's face which results in a Minor Injury Overreaction from Jordan. The icing on the cake is when there's a jump cut to who Venice actually is, a dominatrix who puts Jordan though a brutal BDSM session.
- For pure Comedic Sociopathy, you can't top Donny eating that goldfish.
- Jordan, sobering up from a drugged high of qualudes on a plane trip to Switzerland, finds himself restrained on the airline seat by the captain. Cue a flashback showing a drugged up, hypersexual Jordan attempting to hump and make out with the stewardesses while his friends and other passengers try to stop him. All greatly accompanied by a fast version of Sloop John B.Jordan: "I called the captain the n-word?"
- Put that in perspective: Jordan uses basically every swearword in the English language, is an unfaithful and abusive husband, and makes all his money by conning innocent people...but even he is horrified at the idea that he called a pilot the n-word while he was high on drugs. The fact that he and Donny both say 'the n-word' is even funnier.
- The initial meeting with the Swiss banker.Belfort: (inner monologue) What I'm asking, you Swiss dick, is are you going to fuck me over.Saurel: (inner monologue) I understand perfectly, you American shit.
- The scene in London between Aunt Emma and Jordan, where Jordan assumes that Aunt Emma is flirting with him in his thoughts. When he comes on to her, Aunt Emma thinks in panic ("Is he fucking hitting on me?") and then he kisses her full on the face, which she tells him to back off from, telling him it would be a really bad idea.
- The entire act with the Lemmon Quaaludes is full of these moments.
- To explain, Jordan uses a cocktail of drugs for both recreational and performance enhancing purposes. When Donny botches a money laundering job, he attempts to numb his worries away by inviting Jordan to do some old Quaalude pills that are of a higher dosage than normal. Thinking they expired after taking numerous pills, both men go about their business but later realize that the Quaaludes kick in over an hour late, and hit much harder due to the higher intake. After been forced out of his home to call a private detective on a payphone, Jordan finds out about Donny's botched job only to lose his motor skills midway through the call. Driven to rush back and confront Donny, Jordan begins his slow and agonizing journey crawling across the floor, rolling down a flight of stairs (which looks several times longer to Jordan than in reality), dragging himself to his Lamborghini and driving a mile an hour home. See You Are Already Intoxicated, a variation (listed under Real Life) of You Are Already Dead.
- Returning home, Jordan gets into an comically sloppy fight with Donny over Donny's money laundering screw-up, culminating to Jordan attempting to restrain Donny using a wall phone's cord, which Donny manages to accidentally slingshot back to Jordan's face. When Donny intentionally chokes on some ham in an apparent suicide attempt, Jordan does a vial of coke while a Popeye cartoon plays in the background so that he can save Donny.
- To top it off, we later learn that in reality Jordan drove his Lamborghini as recklessly as someone high on drugs would. This scene is made funnier in a relevant flashback with Jordan road raging while severely impaired, all while his right foot is uncomfortably propped up on the dashboard.
- When Jordan's yacht threatens to sink, he sends Donnie down to grab a bag full of quaaludes, saying in a very deranged tone of voice:Jordan: I will not. Die. Sober!
- Agent Denham's line after arresting Jordan.Denham: Hey, Jordan, let me give you a little legal advice: shut the fuck up!
- In addition, Jordan is arrested while filming a corny commercial for his company. We get to see the scene of his arrest from the point of view of the camera being used to film it, which gets knocked over in the process.
- When Jordan is discussing what finally got him arrested and charged; his partner Rugrat and the French banker who laundered Jordan's money in Switzerland are arrested in Florida, after Rugrat uses Stratton Oakmont to funnel drug money for the guy who founded Benihana's.Jordan: Benihana? Beni-fucking-hana?! BENI-FUCKING-HANA?!! WHY?!!! WHY, WHY GOD?! Why would you be so cruel as to choose a chain of fucking hibachi restaurants to take me down?
Donnie: I'll tell you what, I'm never eating at Benihana again. I don't care whose birthday it is.
- The fact that Jordan is narrating this over footage from a Benihana commercial is icing on the cake.
- The punch-line comes from Donnie's line to Jordan after the fact.
Funny / The Wolf of Wall Street