The movie opens with a TV advertisement for Stratton Oakmont, Inc. It discusses the nature of Wall Street brokers, describing them as bulls or lions. A lion walks through one of the floors of the company.
We next see a large group of brokers playing a game where they throw little people onto a board with a dollar sign for a bulls-eye. Jordan Belfort (Leonardo DiCaprio) then introduces himself among those playing this game. He tells us that he is the son of two accountants living in Bayside, Queens. Ever since he started working on Wall Street, Jordan has enjoyed a life of endless drugs and countless hookers of his choosing. He is seen blowing cocaine into a hooker's butt, and then later flying a helicopter while hopped up on quaaludes. We also see him driving his Ferrari and getting a blowjob from a woman revealed to be his wife Naomi Lapaglia (Margot Robbie). According to Jordan, he does enough drugs to sedate the majority of New York's population. The one drug he loves the most, however, is the one that can make man conquer the world, and that is money. He snorts a line of coke with a $100 bill, crumples it up, and then tosses it in a wastebasket.
When he was 22 years old, Jordan began working on Wall Street while married to a woman named Teresa Petrillo (Cristin Milioti). He starts working as a broker and he meets his smooth-talking, easygoing boss Mark Hanna (Matthew McConaughey), along with another abrasive and foul-mouthed co-boss, Peter DeBlasio (Barry Rothbart). Jordan is astonished at how everybody talks and works. He has a drink with Mark, who is doing a rhythmic chant while pounding his chest. Mark orders enough martinis for them to "pass the fuck out". He asks Jordan how many times he jerks off: Jordan says about three or four times a week. Mark says those are rookie numbers and that he does it at least twice a day. He starts babbling to Jordan about how nobody knows if the stocks will go up, down, sideways, or whatever, and that it's all a "fugazi". Mark's primary reason for going into stocks was pretty much just for hookers and blow. He gets Jordan to join in the "Money Chant".
Jordan starts his first day with his broker's license on what happens to be October 19, 1987 - aka, Black Monday. The stocks around the world plummet, and Jordan loses his job. At home, Teresa suggests they pawn her wedding ring as he looks through the jobs section in the paper. He comes across one place in Long Island: Investor Center located in a small mini-shopping center.
Jordan shows up to Investor Center in a suit. The place is merely a small establishment that hardly looks professional. Jordan is greeted by Dwayne (Spike Jonze), the man who runs the place. He assigns Jordan to pitch a sale for a company called Aerotyne, a small company out of Dubuque, Iowa garage. Aerotyne is also a "pink sheet" (low value) stock and he will receive 50% of the commission. Jordan calls a potential investor about Aerotyne. He sells it to him as a huge company (we're treated to a pic that shows it looking no bigger than a tool shed), but the way he pitches it draws everybody's attention. Everybody in the office stops what they're doing to listen to Jordan, who makes a very slick but also very professional sales pitch. He succeeds in making the sale and his new coworkers are impressed.
After a few months, Jordan is making serious money. He is approached in a diner by a chubby bespectacled man with fluorescent white teeth named Donnie Azoff (Jonah Hill). He asks Jordan if the Jaguar outside is his car, to which Jordan says 'yes'. Donnie says he lives in the same apartment building as Jordan and mentions he works selling children's furniture. He asks Jordan how much money he makes, and Jordan says he made $72,000 the previous month. Not believing it, Donnie asks to see a pay stub for $72,000. Jordan pulls one out, and Donnie calls his boss to tell him he's quitting to go into stocks.
Jordan and Donnie have drinks at a bar. We learn that Donnie married his cousin because he didn't like the idea of anybody else trying to sleep with her. Outside, Donnie smokes some crack and offers some to Jordan. He takes one hit and gets pumped, telling Donnie they need to go running.
The two find a garage where they plan to set up a business. Jordan recruits some of his friends to join. They include Robbie Feinberg (Brian Sacca; nicknamed "Pinhead"), Alden Kupferberg (Henry Zebrowski; nicknamed "Sea Otter"), Chester Ming (Kenneth Choi), Nicky Koskoff (PJ Byrne; nicknamed "Rugrat" because of his shoddy toupee), and Brad (Jon Bernthal). Brad is especially well known for making drug sales in his old neighborhood. Jordan tells Brad to sell him a pen that he pulls out of his pocket. Brad tells him to write something on a napkin. Jordan says he doesn't have a pen, and Brad "sells" it to him. Jordan also brings along several guys from Investor Center, including a guy called Toby Welch (Ethan Suplee).
Jordan and Donnie set up what is basically a boiler room in the garage they find. The guys are all set up at desks, ready to make calls with a script that Jordan wrote for them. They start with blue chip stocks like Disney and AT&T. Jordan calls one investor to purchase stocks in Kodak. Jordan anticipates the deal by making crude sexual gestures to everyone just as the investor signs on. From there, Jordan creates Stratton Oakmont and forms it into a much larger business with even more brokers working for him. He has groups of ambitious and hopeful brokers clamoring in his office showing off their resumes to his face. As one Strattonite makes a sale, the whole floor celebrates, with a marching band and a big group of hookers. They even have one female employee get her head shaved if Jordan pays her $10,000 for her to use for breast implants.
Over the next few years, news of Stratton Oakmont's success gets around, from Forbes Magazine to the FBI, specifically Agent Patrick Denham (Kyle Chandler). Forbes does a piece on Jordan, calling him a "sleazy Robin Hood" and dubbing him "the Wolf of Wall Street." Jordan is at first angry about it, but Teresa tells him there's no such thing as bad publicity and more young and eager brokers flock to his office. They bring on Jordan's father, whom everyone refers to as "Mad Max" (Rob Reiner) due to his constantly irritated attitude. He oversees his son's accounts and berates him and his partners for spending $26,000 for a dinner, interrupting their chat about using the little people for their game (as seen earlier).
Jordan throws a party at his Long Island beachfront house where he announces a plan to take the company "into the FUCKING STRATOSPHERE!" He is about to explain to us the effects of quaaludes, but Donnie suddenly rises and slowly goes over to Jordan's table in slow motion to mumble "Steve Madden." Steve Madden, as Jordan notes, was the big name in women's shoes. Jordan then sees Naomi for the first time. He runs down to introduce himself, inviting her to join him on his jet ski. Donnie's wife Hildy (Mackenzie Meehan) sees this and tries to get Jordan away from Naomi by saying Teresa needs his help. Donnie then goes downstairs and starts masturbating to Naomi in front of the whole party.
Jordan takes Naomi out to dinner one night. When he takes her home, she invites him to her apartment for some tea. Jordan is extremely tempted by her, right before she steps out of her room fully nude. The two have sex for 11 seconds before Jordan tries to get it going again. He continues his affair with Naomi for a while before Teresa catches Jordan doing coke off her breasts in the back of a limo. She pulls Jordan out and starts smacking him. She tearfully asks him if he loves Naomi, but he doesn't reply. Narrating again in voice-over, Jordan says he felt bad about hurting Teresa... and then filed for divorce three days later.
Naomi moves into Jordan's apartment. She hires a decorator to redo the place to Jordan's liking, and she also hires a gay butler named Nicholas (Jon Spinogatti). Jordan likes him until the night that Naomi comes home to find that Nicholas is holding a gay orgy in the apartment. She goes crying to Jordan and tells him that $20,000 in cash is missing from their room as well as $30,000 worth of jewelry and other appliances. Jordan, Donnie, Chester, and Rugrat interrogate Nicholas about what he knows about the missing money. Nicholas refuses to answer questions (clearly protecting his gay friends) and quickly changes the subject by openly telling them that he thinks them questioning him is just gay prejudice. Chester punches him hard in the nose, and he and Donnie hold Nicholas by his legs over the balcony to try to make him confess. Jordan calls the cops, who arrest Nicholas for stealing, and kick his ass instead.
Jordan manages to recover the stolen cash through money laundering. Since he recognizes that these practices are illegal, he hires an attorney, Manny Riskin (Jov Favreau), to keep them clear. All Jordan cares is that he's making more money than he and anybody else can know what to do with.
Jordan proposes to Naomi with a yellow diamond ring. She accepts. He holds a bachelor party in Las Vegas, where even the plane ride consists of a lot of hookers, alcohol and a lot of cocaine. The wedding is also a pretty big event. Naomi introduces Jordan to her English Aunt Emma (Joanna Lumley), who is aware of Jordan's cocaine use. Jordan and Naomi move out of their New York penthouse and buy a large mansion on Long Island. He even buys Naomi a yacht as a wedding gift (it's also named Naomi).
18 months later, Jordan and Naomi have a daughter, Skyler. By this time, the couple is constantly bickering over Jordan's antics. He slept through the night calling the name "Venice". We see she is a hooker who pulled a lit candle out of Jordan's ass during sex and poured the hot wax on his back as he kept screaming "Wolfie" (his safety word). Jordan says this fighting is part of their routine, which ends with them getting intimate. When they put the baby to sleep, Naomi says she is wearing short skirts from now on and won't be wearing panties deliberately to tease Jordan. Jordan however, has his own trick to pull; he tells Naomi that she's been videotaped by Jordan's security guards, both of whom are named Rocco.
At work, it is the day of an IPO meeting with Steve Madden, a ladies shoe designer seeking to go public with his company. Jordan catches a geeky broker cleaning his goldfish tank. He sends Donnie to call the guy out and humiliate him in front of everybody by swallowing the man's goldfish whole and then sending him out while everybody else jeers him on. Steve Madden (Jake Hoffman) goes up to present his latest shoes, the Mary Lous (which one broker says look like fat woman shoes). The brokers start throwing junk at him, which Jordan stops. He wants Madden to join them in business, which he agrees to. Jordan then gets up to the stage to give a speech to the whole floor about the wonders of being rich. The stock is launched in the trading room and becomes a success, netting Stratton Oakmont $22 million in just three hours.
The FBI sends the company a subpoena to request Jordan's wedding video tape. Jordan meets his private investigator, Bo Dietl (playing himself) where Bo tells him that Denham has pictures of Jordan's inner circle. Jordan asks Dietl if it's possible to buy off Denham -- Dietl emphatically says 'no'.
A few days later, Jordan invites Denham and his partner Agent Hughes (Ted Griffin) onto the Naomi moored at a Long Island harbor. He shows them the list of everybody in attendance to the wedding. When Jordan tells Denham of an employee of his that he hired after needing money for his mother's triple bypass surgery, Denham interprets this as some sort of bribe. Jordan laughs it off and sends the agents off his yacht. He mockingly throws money at them as they walk away.
Jordan decides to keep his money safe from the tax men as well as thieves by storing it in offshore accounts. He, Donnie, and Rugrat go to Switzerland to get the job done. The trip there is chaotic for Jordan since he takes a bunch of quaaludes prior to the flight. He then behaves very lewdly toward the stewardess and he insults the pilot. He wakes up strapped to his chair. Donnie tells Jordan that he tried to start a riotous party on the airplane, dry-humping the female flight attendants and insulting the plane's captain, who personally restrained Jordan in his seat. Due to Rugrat's intervention, with assistance from his Swiss friend, Jordan isn't charged upon his arrival.
The trio meets with a group of French Swiss bankers led by Jean Jacques Sorel (Jean Dujardin), Rugrat's friend in college. Sorel persuades them to get someone outside the U.S. to store money in their account. Jordan travels to London, England to convince Naomi's Aunt Emma to take some money. This also leads to Jordan unsuccessfully trying to hit on her. They also use Brad's Slovak wife Chantalle (Katarina Cas) to smuggle money in with her family. Donnie and Brad get into an argument that ends with Brad punching Donnie out.
Some time later, Donnie drives out to a seedy Long Island strip mall to make an exchange with Brad. Brad had specifically asked Jordan to make sure Donnie didn't arrive at the meeting drugged out, but Donnie appears to be anyway. After a few moments, Donnie reveals that he isn't actually stoned for the meeting and begins to provoke Brad -- Donnie had taken very personally the fact that Brad had hit him. They get into another argument with the cops watching nearby. Donnie drops his briefcase of money and flees, leaving Brad to get arrested.
Donnie brings to Jordan a strong brand of quaaludes called Lemmon 714, a very rare version of the drug. The two take a pill each and watch "Family Matters" on the TV, but feel no effects after 35 minutes. They take more and still feel nothing. They find out that they expired in 1981. Naomi (pregnant again) goes downstairs to find the two working out. She tells Jordan that Bo Dietl is on the line. Dietl tells Jordan to go call him from a payphone. Jordan drives to a country club to use the payphone there. Dietl tells him about Brad getting arrested, and that Denham has Jordan's home and work phones tapped. Just then, Jordan starts to finally feel the effects of the Lemmons taking effect. He starts slurring his words and then collapses to the floor, unable to stand or walk. He crawls outside, rolls down the steps, and manages to open the door of his Lamborghini. Naomi calls him to say that Donnie is calling Sorel. Jordan makes an attempt to drive his car home despite being too high. He slowly manages to get home safely and crawls his way out of his car and to the kitchen to pull Donnie (who is also feeling the delayed effect of the quaaludes) off the phone. Donnie runs to stuff cold cuts in his mouth, but he starts choking and falls on top of the glass table. Naomi runs in to find Donnie turning blue and choking. Jordan grabs a little vial of coke from a drawer and pours the whole thing into his nose. This is juxtaposed with a Popeye cartoon as Olive Oyl feeds the sailor man some spinach, with the tune accompanying Jordan and the coke. He pulls the food out of Donnie's mouth and begins to apply a crude form of the Heimlich Maneuver. Jordan pauses for a few seconds, thinking he'll let Donnie die, until Naomi reminds him that Donnie has a family. Jordan finally gets Donnie to cough up the food he was choking on.
Jordan wakes up the next morning to find the police in his house. They arrest him when they show him his Lamborghini, with notable damage, despite Jordan thinking he got the car home in one piece. A flashback shows us that Jordan didn't make it home without damaging his car, hitting several other cars, a few golf carts and a mailbox. He is released after it's determined they have no proof Jordan was ever behind the wheel of the car. Manny and Max tell Jordan he got lucky.
Another few months later, Jordan holds a big meeting on his floor to announce that he is stepping down from the company to pass it onto Donnie, Pinhead, and Rugrat. He calls out one woman for starting at Stratton with "barely two nickels to rub together", and now living rich. He tells the brokers he loves all of them, moving them to tears. Jordan then changes his mind and decides to stay, leading to cheers. He gets everybody to join him in the "Money Chant." His father is not pleased, believing Jordan would be better off in taking the deal the FBI was offering.
Jordan holds a huge celebration on his yacht, right after Brad is released from jail. Brad subsequently quits doing business in stocks, and Jordan tells us he died of a heart attack two years later.
In June 1996, Jordan and Donnie take their wives to Portofino, Italy to continue the celebration. Rugrat calls then while they're drinking Bloody Marys and snorting cocaine to tell them that Steve Madden is unloading shares after hearing about Jordan's recent trouble with the law. To make matters worse, Naomi comes crying to tell Jordan that Aunt Emma died of a heart attack. Jordan is distraught, but more due to the fact that this leaves the $20 million in her account inaccessible. Jordan calls Sorel, who tells him that Aunt Emma named Jordan the successor to the money. He just needs to get to Switzerland immediately. Jordan runs to tell the captain to take them to Switzerland, despite Naomi's insistence that they go to England for the funeral. The captain warns that there may be choppy waters ahead, but Jordan doesn't care. Indeed, they do sail right into dangerous waters. Jordan orders Donnie to run and get more quaaludes, even as Donnie objects -- Jordan doesn't want to die sober. He runs downstairs anyway and brings the drugs up, just as a huge wave breaks through boat and turns it over. The group is rescued by a Italian Navy helicopter called in by Jordan. They're taken on another boat, and Jordan sees the jet crash into the ocean. He tells us this was due to a seagull flying into the engine. He believes this to be a sign from God.
Two years later, Jordan is sobered up. He is seen in an infomercial advertising his moneymaking seminar, Straight Line. During a taping of the infomercial, Denham and other agents arrest Jordan. Sorel had been arrested in Switzerland for crimes unrelated to Jordan, and he ended up ratting him out while having dinner with Rugrat (who is also arrested). Sorel had also been having an affair with Brad's wife whenever she smuggle cash to him in Switzerland. All the members of Stratton refuse to give anybody up to save themselves.
Donnie goes over to Jordan's place as he is under house arrest, he wears a locator on his right ankle. He says he's got Jordan's back in the scheme of things. He also asks Jordan how sober life is. Jordan thinks it sucks. Naomi is also furious with Jordan, refusing to speak to him.
Jordan and his lawyer meet with Denham and two other Department of Justice lawyers. They try to make a deal in which Jordan wears a wire to incriminate the other co-conspirators. They call the case a "Grenada" in reference to the US invasion of Grenada in the Caribbean, where the US government very easily suppressed an invasion of that island nation by Cuba. To them, the case will be easy for the Dept of Justice to win because of the overwhelming amount of evidence they've collected.
A few nights later, Jordan pesters Naomi for sex, and she eventually gives in and asks him to make love "as if it were the last time." Once the two are finished, she tells him it really was the last time; she intends to file for divorce, and tells Jordan that unless he agrees to every condition that she demands (a quick divorce, full custody of the two kids and half of his remaining wealth), she'll take out a restraining order that will bar Jordan from ever contacting her or the kids again. Jordan becomes enraged and insults her; she slaps him and he hits her back harder. He storms into a small sitting room and cuts open one of the sofa cushions, removing a bag of cocaine. He snorts a good-sized amount and runs into Skyler's room taking from her bed. Over Naomi's panicked protests, he runs downstairs to leave with Skyler. Naomi and the Belforts' maid try to stop Jordan as he drives the car out of the garage, but he ends up crashing into a wall just a few yards away. Skyler is unharmed as she was wearing her seat belt, but Jordan suffers a head injury. Naomi takes Skyler out of the car, as a dazed Jordan gradually realizes he will probably never see his two daughters again after this latest incident.
Jordan is set up with the wire to bring in his partners. They all cheer for him upon his return. He goes to start with Donnie. Jordan slides him a note that says "Don't incriminate yourself. I'm wearing a wire." When he asks Donnie about their financial practices, Donnie pretends not to remember anything.
The FBI arrive at Jordan's house to arrest him when they discover the note he slipped to Donnie (though not shown, the note was given to Denham by Donnie himself, likely as part of a deal that will leave Donnie unaffected). While Donnie rapidly deletes any incriminating files on his office computer the rest of the co-conspirators are arrested in the office. In court, Jordan is sentenced to 36 months in prison. His mother cries as her son is taken away while Max looks at him disappointed. When he arrives at prison, Jordan admits that he was terrified when he got there. For a fleeting moment, he says, he forgot that he was rich. He had become so accustomed to a life where everything was for sale.
The final scene takes place at a Straight Line seminar in Auckland, New Zealand (The host is played by the real Jordan Belfort). Jordan comes out to the crowd and stands before one man. He pulls out a pen and tells him to sell it to him. The man awkwardly starts his pitch before Jordan takes the pen away. He hands it to another, who is equally awkward. Jordan continues to do the same with more guests, as all the hopeful future millionaires watch him.