Beat your chest and start that humming chant because Martin Scorsese’s wild ride into true-crime, finance-bro comedy, The Wolf of Wall Street (2013), is a decade old. Since its release, the film has ignited debates – does it glorify the antics of these thieving brokers? (arguably, no, it’s a satire); does it justify its epic three-hour runtime? (absolutely). But today, we’re taking a different approach. It’s time to delve into the moral compass (or lack thereof) of The Wolf of Wall Street cast, assessing just how deplorable each character truly is. We’re setting aside the infamous ringleader, Jordan Belfort himself, portrayed with a slick charm by Leonardo DiCaprio, as his villainy is a given. Let the trading session begin, and let’s rank these wolves!
23. Teresa Belfort
Jordan’s first wife, Teresa (powerfully played by Cristin Milioti), is a beacon of decency amidst the moral decay of Wall Street. She embodies loyalty and support, even accompanying Jordan on his first day of work on the bus. When Black Monday hits and Jordan loses his job, Teresa becomes the provider, sustaining them with her hairdresser income while Jordan wallows in self-pity. It’s Teresa who reignites his ambition, famously declaring, “you’re not gonna be stock bwoi, ’cause you’re a stock brokah!” pushing him towards the Investor’s Center – the initial step on his treacherous climb to wealth. As Jordan accumulates wealth through dubious penny stocks, Teresa’s discomfort grows. She questions the ethical implications, sensing the exploitation inherent in his dealings. Jordan’s heartless dismissal of Teresa, a grounded, working-class woman, marks his definitive break from reality and any semblance of morality. Teresa represents the honest life Jordan abandons, making her the most morally upright figure amongst The Wolf of Wall Street cast. Justice for Teresa, indeed.
22. Judge Samantha Stogel
Representing the unwavering arm of justice is Judge Samantha Stogel, brought to life in a memorable cameo by Fran Lebowitz (for a dose of wit and wisdom, check out Pretend It’s a City [2021], her Netflix series with Scorsese). In the film’s climax, as Jordan finally faces the consequences of his fraudulent empire, Judge Stogel coldly reads out his extensive list of crimes and sets an exorbitant bail of $10 million. Her piercing, disdainful glare before slamming the gavel speaks volumes. Judge Stogel is the embodiment of righteous authority, a stark contrast to the lawlessness Jordan and his cohorts represent. Her presence in The Wolf of Wall Street cast is brief but impactful, symbolizing the ultimate reckoning for the morally bankrupt.
21. Agent Patrick Denham
FBI Agent Patrick Denham, portrayed with world-weary integrity by Kyle Chandler, is the epitome of a straight arrow in a crooked world. Belfort’s own background check confirms Denham’s unblemished character. He operates strictly within legal boundaries, meticulously following procedure in his investigation: issuing subpoenas, monitoring phone lines, and building a solid case against Belfort. Crucially, when Jordan attempts to bribe Denham during a lavish yacht meeting, he remains unyielding. No luxurious lobster, no expensive champagne, no seductive women can sway him. He even rejects the symbolic “fun coupons” (bundles of $100 bills) Jordan mockingly throws at him. Agent Denham stands as a symbol of incorruptibility, a stark reminder of the ethical line Jordan Belfort and his Wolf of Wall Street cast consistently and flagrantly cross. He’s the exception to the rule, a good cop in a narrative saturated with corruption.
20. ‘Mad’ Max Belfort
“This is obscene,” exclaims Jordan’s father, ‘Mad’ Max Belfort (played with comedic exasperation by Rob Reiner) upon visiting his son’s Stratton Oakmont office – a chaotic scene of chimpanzees on roller skates and orgies erupting amidst the financial frenzy. Aside from Teresa, Max is the only character in The Wolf of Wall Street cast to consistently challenge Jordan’s reckless spending and rampant drug use. He questions the morality of excess, reminding Jordan that just because he can spend $25,000 on a single meal, doesn’t mean he should. Max’s concern extends beyond finances; he’s deeply troubled by Jordan’s crumbling marriage. As Stratton’s de facto CFO, Max offers both financial and moral guidance, scolding his son for his blatant infidelity. However, Max is not without his flaws. His explosive temper, earning him the nickname ‘Mad’ Max, reveals a less-than-perfect character. His over-the-top reaction to missing two minutes of The Equalizer (1985-1989) suggests a man struggling to control his own impulses, even as he criticizes his son’s.
19. Captain Ted
Poor Captain Ted, portrayed by Shea Whigham, is the embodiment of an honest man caught in a storm of corruption. As the captain of Belfort’s yacht, the Naomi, he’s simply trying to earn an honest living. Despite dire storm warnings, Jordan pressures him to sail from Italy to Monaco at breakneck speed, driven by a desperate need to access funds from his aunt’s Swiss bank account before they are seized. Ted pays a heavy price for his employer’s recklessness. The yacht is battered by monstrous waves, a helicopter is torn from its moorings, and the windscreen shatters. It’s a near-death experience orchestrated solely to save Jordan’s ill-gotten gains. Captain Ted is left with a shipwreck on his record, profound trauma, and all for the sake of rescuing a multimillionaire’s pocket change. His only failing is his inability to stand up to Jordan, a difficult feat when your livelihood depends on him. Captain Ted represents the collateral damage inflicted by the Wolf of Wall Street cast’s avarice, an innocent man swept up in their destructive wake.
18. Rocco and Rocco
The identically named security guards, Rocco and Rocco (played by Marcos A. Gonzalez and Chris Caldovino), responsible for safeguarding the Belfort estate, are guilty of minor voyeurism. They are caught on CCTV monitors observing Jordan’s second wife, Naomi (Margot Robbie), as she provocatively teases him in the nursery. While it’s true they were on duty and monitoring security feeds, their prolonged attention to this particular feed suggests a breach of professional boundaries. They could have easily shifted their gaze to other cameras but chose not to. Rocco and Rocco represent the pervasive lack of professionalism and unchecked impulses that permeate even the peripheral members of Jordan’s inner circle in The Wolf of Wall Street cast. Harmless pervs? Perhaps, but still a slight moral misstep.
17. Heidi and Nicole
Heidi and Nicole, the pair of attractive blondes present during Jordan’s disastrous attempt to bribe Agent Denham, are essentially bystanders. It’s not their fault Jordan tried to bribe a federal agent; they were simply present for the spectacle. Whether or not they engaged in the alleged act of licking caviar off Jordan’s body, as he boasts, is irrelevant to their moral standing in this ranking. Heidi and Nicole are window dressing, part of the extravagant and morally questionable lifestyle Jordan flaunts, but they are not active participants in the central corruption of The Wolf of Wall Street cast. They are more symbols of Belfort’s excess than perpetrators of any significant wrongdoing themselves.
16. Steve Madden
Steve Madden (played by Jake Hoffman), the real-life shoe designer whose company Stratton Oakmont takes public, presents a moral ambiguity. The film suggests that Madden was likely unaware of Jordan and Donnie’s illegal majority ownership of his company. This is supported by Madden’s swift decision to sell his stock as soon as Jordan’s legal troubles surface. However, Madden did choose Stratton Oakmont to represent his IPO, a firm with a notoriously dubious reputation. As Jordan himself questions, “What person of any substance would trust this bunch of jerk-offs?” Madden’s decision implies either a concerning lack of due diligence or a willingness to overlook ethical red flags for personal gain. While not directly involved in Belfort’s fraud, Steve Madden’s association with Stratton Oakmont places him in a morally grey area within The Wolf of Wall Street cast.
15. Chantalle
Chantalle (Katarina Cas), the Swiss-Slovenian wife of Brad, is actively complicit in Jordan’s criminal activities. She smuggles millions of dollars across international borders for him and recruits her extended family to do the same. While never explicitly confirmed, it’s highly probable she receives financial compensation for her services. Adding to her moral complexity, Chantalle engages in an affair with Jordan’s suave Swiss banker (Jean Dujardin). Chantalle is more than just a bystander; she is a willing participant in Jordan’s money laundering scheme, motivated by personal gain and perhaps a taste for illicit thrills, placing her firmly within the morally compromised characters of The Wolf of Wall Street cast.
14. Brad
Known as the “Quaalude King of Bayside,” Brad (Jon Bernthal) is undeniably shady. His drug dealing past and questionable treatment of women, including demeaning comments towards Chantalle and inappropriate requests from a teenage client, paint him as a morally flawed character. However, Brad operates by his own twisted code. He refuses Jordan’s offer to join Stratton Oakmont, thereby avoiding the majority of the firm’s debauchery (though he does attend the bachelor party). Most surprisingly, Brad demonstrates loyalty by refusing to implicate Donnie, despite their mutual animosity, when questioned by the police, even serving jail time for contempt. Brad’s actions reveal a paradoxical mix of reprehensible behavior and unexpected loyalty, making him a complex, if still morally dubious, member of The Wolf of Wall Street cast.
13. Janet
Jordan’s assistant, Janet (played with sharp intensity by Aya Cash), is a survivor in the toxic, testosterone-fueled environment of Stratton Oakmont. While she has limited screen time, Janet is consistently present amidst the firm’s outrageous behavior. She barks orders, curses at Jordan (“Lick my twat!”), and witnesses the escalating depravity without intervention. Janet’s complicity lies in her active participation in enabling the toxic work environment and, by extension, the firm’s criminal activities. She is present for the strippers in the office, the naked marching band, and the shaving of a sales assistant’s head for money, doing nothing to stop or condemn it. Janet’s ambition and survival instincts lead her to become morally compromised, making her an enabler within The Wolf of Wall Street cast.
12. Naomi Lapaglia
The captivating Duchess of Bay Ridge, Naomi Lapaglia (powerfully portrayed by a young Margot Robbie), Jordan’s second wife, operates in a morally ambiguous space. Legally, Naomi commits no crimes, but she willingly revels in the luxurious lifestyle funded by stolen money. Unlike Teresa’s discomfort with extravagant gifts, Naomi accepts diamond bracelets with “pure, uncomplicated elation.” She is fully aware of Jordan’s illegal activities, overhearing the Swiss bank account scheme and understanding the source of their wealth. Furthermore, Naomi knowingly begins a relationship with Jordan while he is married (though the primary blame for adultery rests with Jordan). However, Naomi redeems herself somewhat by seeking sole custody of her children when Jordan is arrested, protecting them from his corrupting influence. Naomi embodies the allure of wealth and the moral compromises made in its pursuit, a complex figure within The Wolf of Wall Street cast.
11. Aunt Emma
Naomi’s English Aunt Emma (played with delightful mischievousness by Joanna Lumley) is a charmingly amoral character. Her introduction at Naomi’s wedding reception, where she casually brushes cocaine off Jordan’s nose with a knowing, “Into the doughnuts, I see,” establishes her laissez-faire attitude towards his vices. Aunt Emma readily agrees to smuggle money to Switzerland, exploiting her European passport (during the UK’s EU membership) for Jordan’s benefit. She turns a blind eye to Jordan’s sex addiction and embraces a carefree, “good vibes” approach to life, even in the face of blatant immorality. Aunt Emma is undeniably cool and fun-loving, but her willingness to overlook and even participate in Jordan’s criminal enterprise places her on the morally questionable side of The Wolf of Wall Street cast.
10. Manny Riskin
Manny Riskin (Jon Favreau), Jordan’s high-priced securities lawyer, is a morally flexible operator. Charging $700 an hour and indulging in free pastries, Manny’s motivations are clearly self-serving. While he offers warnings about government scrutiny and eventually advises Jordan to cooperate with authorities, his primary interest is in prolonging Jordan’s legal troubles, thus maximizing his own billable hours. Manny is not as overtly criminal as the Strattonites, but he is cut from the same cloth – profiting from Jordan’s misdeeds and prioritizing his own financial gain over ethical considerations. He represents the legal enablers who thrive in the morally murky world depicted in The Wolf of Wall Street cast.
9. Dwayne
Spike Jonze, in his director-turned-actor role, portrays Dwayne, the unscrupulous owner of Long Island’s Investor’s Center. Dwayne’s business model is built on exploitation, preying on vulnerable individuals lured by “get rich quick” schemes advertised in adult magazines. He tricks “schmucks” (his own word) into investing in worthless penny stocks. The Investor’s Center operates outside SEC regulations, a clear legal violation that Dwayne ignores. His sole concern is maximizing profit, regardless of the ethical or legal implications, making him a predatory figure within The Wolf of Wall Street cast, even before Jordan’s ascent to greater infamy.
8. Kimmie Belzer
The Wolf of Wall Street features only one female broker, Kimmie Belzer (Stephanie Kurtzuba), a loud and assertive presence in the pink Armani suit. Initially, Kimmie’s motivations appear somewhat noble – she claims to have entered finance to provide for her child. Jordan portrays himself as her savior, hiring her when she was desperate and facing eviction. However, this narrative conveniently omits Jordan’s self-serving “god complex” in recruiting her. Any initial nobility Kimmie might have possessed is long gone by the time we meet her in the film. Her lavish lifestyle, complete with holiday homes and luxury cars, is funded by stolen money. While her specific involvement in Stratton’s criminal activities is not detailed, she is clearly complicit and benefits directly from the fraud. Kimmie’s resistance to arrest at the end, soundtracked by The Lemonheads’ “Mrs. Robinson” cover, solidifies her position as a morally compromised member of The Wolf of Wall Street cast.
7. Jean Jacques Saurel
Jean Dujardin’s Jean Jacques Saurel, the French-Swiss banker, is knowingly corrupt from his first scene. He immediately uses his connections to prevent Jordan from being arrested after assaulting a flight attendant. Jean Jacques then actively assists the Strattonites in hiding their illicit wealth through Switzerland’s notoriously secretive banking system. His on-screen actions are just the tip of the iceberg, as he is later arrested in Miami for laundering money through offshore boat racing. Jean Jacques is a professional enabler of financial crime, a sophisticated and morally bankrupt figure who facilitates the excesses of The Wolf of Wall Street cast.
6. Sea Otter
Here begins the final descent into the core Strattonites, where moral distinctions become razor-thin. These are venture capitalists willing to betray anyone for profit. Alden Kupferberg, nicknamed “Sea Otter” (Henry Zebrowski), is ranked lower due to his apparent lack of intelligence. His colleagues seem to consistently exploit his dim-wittedness. Sea Otter’s ignorance, exemplified by his lack of a high school diploma and misinformed views on nuns, suggests a level of cluelessness that, while not excusing his actions, positions him as perhaps slightly less culpable than his more cunning colleagues within The Wolf of Wall Street cast.
5. Pinhead
Robbie ‘Pinhead’ Feinberg (Brian Sacca) edges out Sea Otter for similar reasons of perceived intellectual deficiency. He took five years to finish high school and struggles to understand a Moby Dick reference. Pinhead’s lack of awareness is further highlighted by him being the first Stratton employee arrested during the FBI raid. While not a significant moral differentiator, Pinhead’s apparent dimness places him slightly lower in the depravity ranking among The Wolf of Wall Street cast, suggesting a level of unwitting participation in the firm’s crimes.
4. Chester Ming
Another of Jordan’s old friends, Chester Ming (Kenneth Choi), transitioned from selling tires and hash to Stratton Oakmont thanks to Jordan’s “legitimizing” influence. Like Sea Otter and Pinhead, Chester is portrayed as somewhat unintelligent, failing even Jordan’s simple “sell me this pen” test. His sales incompetence suggests that his wealth is likely derived from fraudulent activities like manipulating financial records, rather than genuine salesmanship. Chester’s presence in The Wolf of Wall Street cast underscores how Jordan elevated less-than-capable individuals into positions of power within his corrupt empire.
3. Rugrat
Nicky Koskoff, nicknamed “Rugrat” due to his conspicuous hairpiece (PJ Byrne), is significantly more morally reprehensible. His law school background makes him the most intellectually equipped of the Stratton staff, and he weaponizes this knowledge for malicious purposes. Unlike some of his seemingly clueless colleagues, Rugrat displays genuine malice. He is shown celebrating with disturbing enthusiasm upon learning of a client’s wealthy relative’s death, directly linking client misfortune to personal gain. Rugrat’s most damning moment is his central role in the stomach-churning dwarf-tossing discussion, where he dehumanizes entertainers to minimize legal repercussions. Nicky “Rugrat” Koskoff’s calculated cruelty and legalistic justifications for inhumane acts place him among the most morally bankrupt members of The Wolf of Wall Street cast.
2. Mark Hanna
Mark Hanna (Matthew McConaughey), Jordan’s initial mentor, is the catalyst for Belfort’s descent into depravity. Their infamous lunch scene is pivotal, with Hanna outlining his cynical philosophy of Wall Street: “Fuck the clients! Name of the game? Move the money from your client’s pocket into your pocket.” Hanna’s toxic influence permeates the entire film. Jordan later mimics Hanna’s martini order and adopts his cocaine use as a professional necessity. Hanna openly advocates for greed and self-interest, even recommending thinking about money during masturbation. Mark Hanna is the ideological architect of Jordan Belfort’s moral collapse, making him a profoundly corrupting figure within The Wolf of Wall Street cast, setting the stage for all the subsequent excesses.
1. ‘Diamond’ Donnie Azoff
Unsurprisingly, Jordan’s right-hand man, ‘Diamond’ Donnie Azoff (Jonah Hill), claims the top spot as the most morally bankrupt member of The Wolf of Wall Street cast, excluding Jordan himself. Donnie is closest to Jordan and fully immersed in his depraved world. His rapid descent into corruption is evident in his impulsive resignation from a children’s furniture sales job upon seeing Jordan’s exorbitant paycheck. Donnie’s extensive list of misdeeds includes smuggling drugs, public indecency, animal cruelty (eating a goldfish), and illegal IPO manipulation. His treatment of Brad, who is doing him a favor, is particularly reprehensible, culminating in Brad’s arrest. Even Donnie’s supposed “come-to-Jesus” moment during the yacht storm proves fleeting; he remains unchanged upon returning to shore. His marriage to his cousin, while not legally criminal, further underscores his moral compass’s severe dysfunction. Donnie Azoff embodies the unchecked greed and depravity at the heart of The Wolf of Wall Street, making him the most deserving recipient of the “most deplorable” title among this already morally compromised cast.
