Summary

• "The Wolf of Wall Street" is a cultural phenomenon, and these recommended movies capture the engaging crime and comedy elements of the film.
• "Moneyball," "Pain & Gain," and "The Big Short" all feature charismatic lead characters with unconventional thinking in their respective industries.
• These movies, like "The Wolf of Wall Street," explore themes of corruption, ambition, and the consequences of pleasure-seeking and vindictive personalities.

The Wolf of Wall Street was nothing short of a cultural phenomenon, spawning parodies, internet memes, and instantly quotable lines aplenty, and the best movies like Wolf of Wall Street had a similar impact. Martin Scorsese’s expletive-laden biographical crime comedy saga has become much more than just a pop culture staple. It's the story of real-life scammer Jordan Belfort vividly brought to life thanks to standout performances from the likes of Leonardo DiCaprio, Jonah Hill, and Margot Robbie, and it acts as something of a parable, warning audiences of what pleasure-seeking and vindictive personalities can lead to.

Nevertheless, The Wolf of Wall Street is also a lot of fun, as it walks the fine line between glamorizing Jordan Belfort's life and looking at it through a critical lens. The movie chronicles the incredible highs and dangerous lows of Belfort’s rampant corruption and fraud on Wall Street. The Wolf of Wall Street sits at such a critical point in the history of the crime movie that there are several movies from before and after the movie's release. From the 1960s to the 2020s. the best movies like Wolf of Wall Street encompass engaging crime and comedy.

1 Moneyball

2011

Moneyball is based on the true story of Billy Beane (Brad Pitt), the general manager of the Oakland Athletics baseball team. The manager faced budget restrictions but still turned the Oakland Athletics into a winning team with his revolutionary approach to team building. On paper, it seems completely different from the 2013 movie. However, like the Scorsese epic, Moneyball features a charismatic lead character with unconventional thinking compared to other professionals in the industry. Just like The Wolf of Wall Street, the movie earned Jonah Hill an Oscar nomination for Best Supporting Actor too.

Beyond its surface-level sports story, Moneyball delves deep into themes of perseverance, innovation, and the challenges of disrupting established systems, drawing a subtle parallel to the ambitious and boundary-pushing ethos in The Wolf of Wall Street. Moreover, both films expertly blend drama with moments of light-hearted humor, making complex subjects accessible and entertaining to a wide audience. This similarity in handling serious topics with a touch of levity further connects Moneyball with The Wolf of Wall Street, showcasing the versatility and range of Jonah Hill and the depth of storytelling in both movies.

2 Pain & Gain

2013

Pain & Gain was a surprisingly stripped-back movie for director Michael Bay at the time, as the crime comedy followed a string of big-budget Transformers films. The 2013 release follows a trio of opportunistic body-building thieves who attempt to steal millions from a wealthy businessman in Miami. The film is one of the best movies like Wolf of Wall Street due to how it follows real-life criminals who aren't that smart, and it's extremely stylish with its Florida setting. However, the Pain & Gain characters exist solely to be laughed at, and there's no living vicariously through the crooks.

The film takes a darkly comedic approach to its portrayal of greed and delusion, emphasizing the absurdity of its characters' endeavors without inviting the audience to aspire to their lifestyle. This contrast in character treatment underscores the broader theme shared with The Wolf of Wall Street: the perilous pursuit of the American Dream can lead to wildly different outcomes, depending on the intelligence and morals of those in pursuit. Pain & Gain, therefore, stands out as a unique reflection on ambition and morality, wrapped in the sun-drenched, muscle-bound veneer of Miami's fitness scene.

3 The Big Short

2015

The Big Short is a satirical look at the events leading up to the 2008 financial crisis, and the movie follows investors who predicted the crash and bet against it. Both movies break the fourth wall, but while Leonardo DiCaprio narrates and sometimes speaks directly to the camera in The Wolf of Wall Street, The Big Short takes it much further. As the 2015 movie can often get complicated, those moments cut to famous people breaking the narrative down in layman's terms, such as the Big Short Margot Robbie cameo where she's in a bathtub speaking directly to the camera about investments.

This innovative storytelling method not only demystifies the financial jargon but also adds a layer of accessibility and entertainment, echoing the dynamic and engaging narrative style found in The Wolf of Wall Street. Furthermore, The Big Short’s exploration of greed, corruption, and the consequences of excessive risk-taking mirrors the thematic concerns of The Wolf of Wall Street, presenting a critical yet humorous examination of financial excesses.

4 The Great Gatsby

2013

The Great Gatsby might not have a satirical element to all the wealth and excess that's depicted in the movie, but like The Wolf of Wall Street, the post-modern Baz Luhrmann-directed film is soaked in extravagance with its over-the-top parties. The movie is set in the 1920s and follows Nick Carraway (Tobey Maguire), who gets involved with his mysterious neighbor, Jay Gatsby (DiCaprio). Between the charismatic lead actor, the exploration of decadence, and the American Dream, both 2013 movies share a lot of similarities, and they're both fun and exciting glimpses into opulent lifestyles fueled by ambition.

The Great Gatsby and The Wolf of Wall Street resonate on a thematic level as well, as both delve into the allure and consequences of decadence, the pursuit of success, and the moral compromises that often accompany them. These movies stand as vivid, thrilling portrayals of different eras in American history, yet they parallel each other in their exploration of how ambition and desire can lead to both triumph and tragedy, capturing the imagination with their stories of excess and the pursuit of the elusive American Dream.

5 American Psycho

2000

American Psycho follows Patrick Bateman (Christian Bale), a wealthy investment banker who is also a sadistic serial killer. The 2000 satirical movie shares thematic similarities with the Scorsese film, such as the dark underbelly of success and ambition. It's easy to imagine Jordan Belfort having the very conversation about business cards that Bateman has. However, as American Psycho is completely fictional, the film can go places where The Wolf of Wall Street can't.

However, American Psycho ventures into darker, more surreal territory, with its narrative steeped in murder and psychological twists, and American Psycho ends completely open to interpretation. This blend of horror, satire, and a critique of capitalist excess makes American Psycho a compelling counterpart to The Wolf of Wall Street, offering a unique perspective on the destructive potential of unchecked ambition and vanity.

6 Boiler Room

2000

Long before The Wolf of Wall Street made it into multiplexes, another slick crime film gave moviegoers a glimpse of the murky side of Wall Street. Boiler Room may not have the wit of Scorsese’s movie, but it’s still an entertaining thriller chronicling the rise and fall of Giovanni Ribisi’s Seth, a college drop-out who joins a brokerage firm with dreams of getting rich quick only to realize it comes at a cost. With early standout supporting turns from Vin Diesel and Scott Caan and an appearance from Ben Affleck, Boiler Room is sharply written and well-paced.

Like The Wolf of Wall Street, it delves into the intoxicating allure of financial success and the catastrophic personal consequences that often accompany unethical business practices. The film paints a compelling portrait of the high-stakes world of finance where ambition can lead to ruin, drawing a parallel to the moral complexities and the sometimes devastating effects of greed showcased in The Wolf of Wall Street. Boiler Room, with its critical look at the seductive power of Wall Street and the ethical dilemmas faced by its protagonists, offers a gripping narrative that complements the themes explored in Scorsese's film.

7 Glengarry Glen Ross

1992

Adapted from David Mamet’s Pulitzer Prize-winning play of the same name, Glengarry Glen Ross is an underrated '90s movie. Boasting a stellar ensemble cast that includes Jack Lemmon, Al Pacino, Ed Harris, Kevin Spacey, and a scene-stealing cameo from Alec Baldwin, it’s certainly among the most vivid depictions of the cutthroat world of business and a worthy companion piece to The Wolf of Wall Street. Set primarily in the offices of a real estate firm, it chronicles the efforts of four salesmen desperately trying to cut deals after learning two of them will be fired later that week.

The film excels in showcasing the raw desperation and moral ambiguity that can pervade the pursuit of success, themes that resonate with The Wolf of Wall Street. Through its intense dialogues and the high-stakes pressure of sales culture, Glengarry Glen Ross uncovers the darker side of the American Dream, mirroring the ruthless ambition and ethical compromises seen in Scorsese’s depiction of Jordan Belfort’s life. Moreover, the movie’s critical look at the lengths individuals will go to achieve success, coupled with its exploration of the consequences of such ambition, aligns closely with the thematic underpinnings of The Wolf of Wall Street.

8 Goodfellas

1990

The style of editing that Scorsese had cultivated with his longtime creative collaborator Thelma Schoonmaker was already very famous and well-respected by the time Goodfellas came out. However, this true-crime movie elevated it into the blisteringly energetic format that was used again in The Wolf of Wall Street and emulated in so many other movies. Following the criminal career of notorious former mobster Henry Hill, the movie created what is practically its own genre at this point, taking Scorsese's humanization of the most unsympathetic characters imaginable and applying it to a nonlinear retelling of a sprawling historical epic.

This cinematic approach not only showcases Scorsese's unique narrative style but also his ability to engage audiences with complex, morally ambiguous characters. Like The Wolf of Wall Street, Goodfellas explores the seductive power of wealth and the dark side of the American dream, offering a gritty, unflinching look at the lives of those who pursue it at any cost. Both films use a dynamic, fast-paced editing style that immerses viewers in the whirlwind of their protagonists' lives, making the experience intensely personal and vivid.

9 War Dogs

2016

Jonah Hill was mainly known for his work in teen comedies like Superbad, but he showed hidden depths of his abilities alongside DiCaprio and continued that in War Dogs. Paired alongside the always watchable Miles Teller, Hill plays Efraim, a wannabe businessman who convinces his childhood friend to partner with him as an arms dealer. The pair soon find themselves out of their depth after securing a $300 million deal to supply Afghan forces.

Hill shines as the increasingly unstable Efraim in what is only one of the many crime dramas and best movies like Wolf of Wall Street. War Dogs, like The Wolf of Wall Street, delves into the themes of greed and ambition, showcasing how quickly success can spiral into chaos when moral boundaries are crossed. Both films feature charismatic leads who navigate through morally ambiguous waters, making risky decisions in pursuit of wealth and power.

10 The Founder

2016

A more subtle adaption of a true story, The Founder focuses on the real-life exploits of Ray Kroc, a struggling salesman who discovers and sets about turning McDonald’s into the biggest fast-food restaurant chain in the world. Featuring a powerhouse performance from Michael Keaton as Kroc as well as impressive supporting turns from Nick Offerman and John Carroll Lynch as the naïve pairing of Richard and Maurice McDonald, The Founder doesn't have the flashy approach or the colorful language of The Wolf of Wall Street, but it's a fascinating exploration of the dark side of the American dream.

Through its portrayal of Kroc's relentless drive and innovative, if ruthless, business tactics, The Founder presents a gripping tale of how ambition can reshape an industry and redefine what it means to achieve the American dream. It examines the cost of success, not just in financial terms but also in personal and ethical ones, offering a compelling parallel to the high-stakes financial world of Jordan Belfort. Both films ultimately showcase the exhilarating yet perilous journey of redefining success and the impact it has on those who dare to chase it.

11 I, Tonya

2017

Margot Robbie cemented her status as a bona fide A-lister with this Oscar-nominated turn as disgraced figure skater Tonya Harding. The film is a warts-and-all black comedy chronicling one of the most infamous incidents in US sporting history; Harding allegedly schemed to have a rival taken out in the build-up to the Olympics. Robbie makes the troubled skater a complicated, compelling, and strangely sympathetic character. Director Craig Gillespie excels in chronicling the heavily disputed “facts” of the case as well as the fallout from it, while Allison Janney earned an Academy Award for her supporting turn as Harding’s poisonous mother.

Allison Janney’s portrayal of Harding’s harsh and domineering mother earned her an Academy Award for Best Supporting Actress, adding another layer of critical acclaim to the film. Like The Wolf of Wall Street, I, Tonya explores the themes of ambition, scandal, and the pursuit of success at all costs, albeit in a completely different arena. Both films offer a deep dive into the lives of their protagonists, shedding light on their motivations, the consequences of their actions, and the societal pressures that drive them to extreme measures.

12 Wall Street

1987

The film that inspired Jordan Belfort and countless others to pursue a career on Wall Street, Oliver Stone’s movie offers a fascinating look at the archetypal portrayal of 1980s success. While the action follows the exploits of Charlie Sheen’s junior stockbroker Bud, Wall Street undoubtedly belongs to Michael Douglas. He earned the Best Actor Oscar for his performance as Gordon Gekko, Bud’s shady boss whose willingness to do whatever it takes to turn a profit proves his undoing. His classic line “greed, for lack of a better word, is good” was one of the most quoted of the decade.

In the vein of The Wolf of Wall Street, Wall Street delves deep into the ethos of financial excess and the ethical dilemmas that come with it, painting a vivid picture of ambition and corruption. The portrayal of Gekko as a charismatic yet morally ambiguous character mirrors the complex personalities at the heart of Scorsese's film. Both movies critically examine the allure and consequences of unchecked ambition within the competitive arena of finance, making Wall Street a seminal film that remains a critical touchstone for understanding the dynamic and often problematic allure of the financial industry.

13 Thank You For Smoking

2005

This searing satirical black comedy shares the same DNA as The Wolf of Wall Street, buoyed by a career-best turn from Aaron Eckhart. The actor plays Nick Naylor, a smarmy spokesman for Big Tobacco, juggling the dual demands of being a lobbyist spinning half-truths for cigarette manufacturers and being a father and role model to his 12-year-old son. Thank You For Smoking is a witty and deliciously dark movie that achieves the feat of being both hilarious and deeply depressing, making it one of the best movies like Wolf of Wall Street.

Like The Wolf of Wall Street, it delves into the morally ambiguous world of high-stakes lobbying with a charismatic lead who uses wit, charm, and underhanded tactics to navigate the complexities of an industry many love to hate. The film's exploration of themes such as success, morality, and the power of persuasion mirror the intricate dynamics seen in The Wolf of Wall Street, presenting a compelling look at the lengths individuals will go to achieve success and influence, regardless of the ethical costs.

14 The Aviator

2004

Leonardo DiCaprio has collaborated with Martin Scorsese on six films, and while The Wolf of Wall Street and The Departed may be among the most celebrated, arguably DiCaprio's most complete and complex performance comes in The Aviator. A stunningly realized biopic chronicling the life and times of aviation pioneer and director Howard Hughes, DiCaprio brilliantly captures the business magnate's increasingly unstable mental state as he wrestles with the severe obsessive-compulsive disorder that would ultimately turn Hughes into a recluse. It’s a gorgeous film showcasing the Golden Age of Hollywood while offering insight into a truly fascinating figure from the period.

The Aviator, much like The Wolf of Wall Street, explores themes of ambition, success, and the personal cost of achieving greatness. Both films feature DiCaprio in roles that challenge the limits of their character's ambitions and the impacts those ambitions have on their personal lives and mental health. The portrayal of Howard Hughes's struggles with mental illness and his efforts to overcome personal and societal limitations parallels Jordan Belfort's relentless pursuit of wealth and excess in The Wolf of Wall Street.

15 Margin Call

2011

The Big Short is the popular pick when it comes to films about the 2008 global financial crash, but Margin Call is the less showy, more substantial pick in the niche subgenre and one of the best movies like Wolf of Wall Street. Taking place over a dizzying 24-hour period at a fictional Wall Street investment bank, it chronicles the terrifying initial stages of the crisis and a group of employees' doomed attempts at rescuing the situation. With fine turns from Zachary Quinto and Stanley Tucci, it’s Jeremy Irons who steals the show as one of the firm’s senior partners.

Margin Call's strength lies in its intense focus on the moral and ethical decisions faced by individuals at the brink of financial ruin, mirroring the themes of greed and ambition explored in The Wolf of Wall Street. The film's quieter, more reflective approach provides a stark contrast to the high-octane energy of Scorsese’s work, yet both movies offer a penetrating look into the complexities of financial systems and the human behaviors that drive them.

16 The Social Network

2010

David Fincher took an entirely different–but just as contemporarily relevant–look at unhealthy behavior in this dramatization of the events surrounding Facebook. The lives of the main characters are much more restrained than the gangster-adjacent energy of The Wolf of Wall Street, but the impact of their work and the implications of their moral dubiousness is far more concerning than even the culture of corruption within the financial world.

The allure of success and excessive wealth are still very much a part of the story, but Jesse Eisenberg's take on Mark Zuckerberg in The Social Network cast is a chilling protagonist. With its focus on the implications of technological advancement and social media on society, the film extends the conversation about the American dream and the costs of achieving it, making The Social Network a compelling companion to The Wolf of Wall Street for those fascinated by the interplay of power, success, and morality.

17 The Death of Stalin

2017

Worlds don't get any more cutthroat than the culture within the highest levels of the Soviet Union after Joseph Stalin's death, and comedies don't get any darker than Armando Iannucci's take on the power struggle between the key members of the leader's inner circle. Steve Buscemi leads the cast as Nikita Khrushchev caught somewhere between a classic political miser from Veep or The Thick of It and his days as a mob boss in Boardwalk Empire. The talented cast of supporting players delivers hilarious scenes based on some of the bleakest subject matter from modern history.

While The Death of Stalin and The Wolf of Wall Street occupy vastly different settings and genres, they share a sharp, satirical edge that dissects power dynamics and ambition. Iannucci's film, much like Scorsese's, uses humor to explore the absurdities and moral ambiguities of its characters' actions. The cutthroat politicking and backstabbing for power in The Death of Stalin echo the aggressive pursuit of wealth and status in The Wolf of Wall Street, offering a darkly comic perspective on the lengths individuals will go to achieve and maintain power.

18 La Dolce Vita

1960

• Not available to rent or stream

There are few filmmakers that Scorsese has as frequently cited as a primary influence on their work than Federico Fellini, and the Italian director's 1960 masterpiece offers a fascinating reference point for Scorsese's examination of unhappiness and excess in modern life. La Dolce Vita's depiction of the ugly side of beauty is why it's one of the best movies like Wolf of Wall Street. After all, La Dolce Vita was so astute in its observations of fame and obsession for the wealthy that it's the origin of the modern word 'paparazzi.

La Dolce Vita explores the life of Marcello Rubini, a journalist on the hunt for the next big scandal, navigating through parties filled with the elite of Rome's society. Like The Wolf of Wall Street, it delves deeply into themes of decadence, disillusionment, and the search for meaning in a materialistic world. Both films are opulent visual feasts that showcase the allure and the eventual emptiness of chasing after hedonistic pleasures. Marcello, much like Belfort, undergoes a journey that questions the value and the cost of their lifestyles, making both movies poignant studies of their protagonists' internal and external worlds.

19 Casino

1995

Reteaming Scorsese with Goodfellas' co-writer Nicholas Pileggi, as well as stars Robert De Niro and Joe Pesci, Casino is another tale of greed, power, and loyalty that begins with De Niro’s casino executive Sam ‘Ace’ Rothstein engulfed in a ball of flames before working backward to explain how he ended up there. Pesci plays to type as mob enforcer Nicky Santoro, while Sharon Stone deserves the biggest plaudits as Ace’s troubled wife Ginger, a performance that certainly laid some of the groundwork for Margot Robbie's successful turn in The Wolf of Wall Street.

Like The Wolf of Wall Street, Casino delves deep into the complexities of its characters, driven by their desires for more—more money, more power, more control. The film explores the glittering facade of Las Vegas’ gambling empire and the brutal, often violent realities that underpin it, mirroring the themes of ambition and corruption prevalent in The Wolf of Wall Street. Both movies masterfully depict the rise and fall narratives of their protagonists, anchored by Scorsese's dynamic direction and the compelling performances of their leads.

20 The Irishman

2019

The Irishman is one of the best movies like The Wolf of Wall Street. Scorsese, De Niro, and Pesci teamed up once again to adapt another true crime mafia legend, this time revolving around the hitman Frank Sheeran and his supposed involvement in some of the key events of American history in the latter half of the 20th century.

Though De Niro's Sheeran is a much devilish character to have sympathy for, Scorsese explores the humanity of a fairly unrepentant monster through Sheeran. The Irishman, with its deep dive into the life and times of Sheeran, offers a reflective look at the consequences of a life of crime, contrasting with the frenetic pace of The Wolf of Wall Street but similarly engaging with the director's interest in the darker sides of ambition and success. The movie more than lives up to the legacy of the director's other achievements in the genre as well as continuing to further them.