25 Movies To Watch If You Love The Wolf Of Wall Street

25 Movies To Watch If You Love The Wolf Of Wall Street

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.

25 Catch Me If You Can (2002)

Leonardo DiCaprio Con Movie

Catch Me If You Can Where to Watch

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Director Steven Spielberg Release Date December 25, 2002 Distributor(s) DreamWorks Distribution Cast Leonardo DiCaprio , Tom Hanks , Christopher Walken , Martin Sheen , Nathalie Baye , Amy Adams , James Brolin , Brian Howe

In The Wolf of Wall Street, Leonardo DiCaprio plays Jordan Belfort, a man who scammed countless people to become a very rich and powerful person. However, Martin Scorses tells this story as a dark comedy, with Jordan as the main point of view and oblivious to the damage he was causing and the devastating downfall coming his way. In the Steven Spielberg movie, Catch Me If You Can, DiCaprio is also the lead as a man who cons plenty of people to get what he wants.

Both
Catch Me If You Can
and
The Wolf of Wall Street
are based on books by the real-life criminals they tell the story of.

This is a good movie to watch alongside The Wolf of Wall Street, as it shows DiCaprio playing two dishonest people in very different ways, but both movies have a lighter touch. While not as dark as Scorsese’s movie, Catch Me If You Can as DiCaprio as Frank Abagnale Jr., who spends the entire movie stealing identities from people and living his best life while an FBI agent (Tom Hanks) is hot on his tail. Frank is more sympathetic, but both men are criminals who eventually pay for their crimes.

24 Dumb Money (2023)

The GameStop Stock Scandal

Dumb Money Book Cover Dumb Money Where to Watch

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Director Craig Gillespie Release Date September 15, 2023 Distributor(s) Sony Pictures Releasing Cast Paul Dano , Pete Davidson , America Ferrera , Nick Offerman , Anthony Ramos , Sebastian Stan , Shailene Woodley , Seth Rogen , Dane DeHaan , Myha’la Herrold , Talia Ryder , Clancy Brown , Kate Burton , Larry Owens , Olivia Thirlby , David Faber Expand

The Wolf of Wall Street is about Jordan Belfort, a stockbroker who became wealthy by defrauding his clients while trading their stocks. Anyone who wants to see a more light-hearted but still amazing story of the stock market should check out the movie Dumb Money.

This is based on real-life stock market trading in 2021 when people on Reddit began working together to buy and sell stock to force a rise in the value of the video game store GameStop. The movie stars Paul Dano, Seth Rogen, Pete Davidson, Vincent D’Onofrio, and America Ferrera as the real-life people involved in the stock trading that caught the attention of Congress, who stepped in to do something to stop it.

What these people were doing was not unlike big-money traders, but because they were just regular people, a Congressional hearing shut them down. The movie earned positive reviews from critics, although it was a box office bomb.

23 Pain Hustlers (2023)

A Pharmaceutical Corporate Drama

Pain Hustlers (2023) - Poster - Emily Blunt & Chris Evans Pain Hustlers (2023)

Director David Yates Release Date October 20, 2023 Studio(s) Grey Matter Productions , Wychwood Media Cast Emily Blunt , Chris Evans , Catherine O’Hara , Jay Duplass , Andy Garcia

Pain Hustlers is a Netflix movie starring Emily Blunt and Chris Evans about a company that sells pain medication to cancer patients. Unlike The Wolf of Wall Street, this is not based on a true story. However, it is based on a real problem in the world: pharmaceutical companies often take advantage of the weak and despondent.

In this movie, Emily Blunt plays a single mother with an epileptic daughter who is offered a job at Zanna, where she convinces doctors to prescribe pain medication to cancer patients. Unlike The Wolf of Wall Street, where Jordan’s only goal is to become as wealthy as possible and live the highest of lives, this movie tries to paint Liza as a mother who wants to make things work for her and her daughter.

This causes the two movies to send different messages, with Wolf of Wall Street showing the downfall of a bad man and Pain Hustlers mostly ignoring the victims who become addicted to the dangerous medicine and making Liza, one of the villains of the story, the victim instead.

22 The Gentlemen (2019)

Matthew McConaughey As A Different Kind Of Businessman

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Director Guy Ritchie Release Date January 24, 2020 Writers Guy Ritchie Cast Henry Golding , Jeremy Strong , Matthew McConaughey , Colin Farrell , Hugh Grant , Charlie Hunnam , Michelle Dockery

In The Wolf of Wall Street, Matthew McConaughey played Mark Hanna, the man who taught Jordan Belfort everything he knows about working as a stockbroker and defrauding as many people as possible to make as much money as possible. One of the best scenes in the movie is when Mark is at a dinner with Jordan and explains why their job is the best in the world. McConaughey has another movie where he plays a successful person in business, but this time, it is illegal dealings.

The Gentlemen
spin-off series streams on Netflix.

Guy Ritchie directed The Gentlemen in 2019, a movie where McConaughey plays Michael “Mickey” Pearson, an American who sells cannabis wholesale in England. He has become very successful and very wealthy, but he is ready to step down and wants to sell his business. However, people want the business for themselves and don’t want to pay for it. The movie was so successful that it became a spin-off streaming series on Netflix with Theo James starring as Mickey.

21 There Will Be Blood (2007)

The Story Of How Oil Ruined Small Towns

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Director Paul Thomas Anderson Release Date December 26, 2007 Distributor(s) MiraMax Cast daniel day-lewis , Russell Harvard , Ciarán Hinds , Dillon Freasier , Paul Dano , Kevin J. O’Connor

The Wolf of Wall Street was about a man who ruined people’s lives for years to become wealthier himself. The P.T. Anderson movie There Will Be Blood has a similar story. Based on the Upton Sinclair book, Oil!, the movie stars Daniel Day-Lewis as Daniel Plainview, a man who comes into small towns to buy land, plant his oil rigs, and then sucks the towns dry before moving on to the next town. He meets someone who stands up to him in Paul Dano’s preacher, Eli Sunday.

There Will Be Blood
won two Oscars with eight nominations.

There Will Be Blood is a deep story, much more so than The Wolf of Wall Street. The movie is clearly influenced by horror movies like Dracula, with Daniel Plainview as the vampire who comes into town and drains it of its lifeblood before moving on. The fact he meets a young preacher who stands up to him is no coincidence either. However, also unlike the Scorsese movie, the villain here is destroyed by the end (he loses his son Henry), but he comes out as the victor over the young preacher.

20 Moneyball (2011)

Business In The World Of Baseball

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Based on the book by Michael Lewis, Moneyball chronicles the Oakland A’s general manager Billy Beane as he attempts to assemble a baseball team on a lean budget – by employing computer-generated analysis to acquire new players. Billy partners with a young and hungry economist, played by Jonah Hill, as they develop an unconventional team of players that will change the game of Baseball forever.

Director Bennett Miller Release Date September 23, 2011 Cast Brad Pitt , Jonah Hill , Robin Wright , Philip Seymour Hoffman , ​Chris Pratt2 Runtime 133 minutes

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.

19 Pain & Gain (2013)

Bodybuilders Plan Out A Kidnapping & Extorsion Scheme

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Pain & Gain features Mark Wahlberg, Dwayne Johnson, and Anthony Mackie as three Miami bodybuilders who get caught up in a kidnapping and extortion scheme that goes awry. The 2013 action comedy, directed by Transformers director Michael Bay, is based on the true story of the real-life Sun Gym gang.

Director Michael Bay Cast Mark Wahlberg , Dwayne Johnson , Anthony Mackie , Tony Shalhoub Runtime 129minutes Release Date April 23, 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 of ambition and morality, wrapped in the sun-drenched, muscle-bound veneer of Miami’s fitness scene.

18 The Big Short (2015)

Based On The 2007-2008 Financial Crisis

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A fictionalized depiction of the events surrounding the financial crisis of 2007-2008, The Big Short employs narrative techniques such as fourth-wall breaks to succinctly explain financial concepts to its audience, using Michael Lewis’s 2010 book as a template. The film features an ensemble cast that includes Christian Bale, Steve Carell, Ryan Gosling, and Brad Pitt. 

Director Adam McKay Release Date December 23, 2015 Cast Brad Pitt , Melissa Leo , Ryan Gosling , Marisa Tomei , Steve Carell , Christian Bale Runtime 130minutes

The Big Short is a satirical look at the events leading up to the 2008 financial crisis, following 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 further.

As the 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.

17 The Great Gatsby (2013)

Leonardo DiCaprio In The F. Scott Fitzgerald Adaptation

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The Great Gatsby is a 2013 drama romance film based on the book of the same name by F. Scott Fitzgerald. The movie is one of many adaptations of the iconic 1925 novel, this time starring Leonardo DiCaprio as Jay Gatsby and Tobey Maguire as Nick Carraway. The film received a polarizing reception upon release but won two Oscars at the 2014 Academy Awards.

Director Baz Luhrmann Release Date May 10, 2013 Cast Leonardo DiCaprio , Carey Mulligan , Joel Edgerton , Tobey Maguire , Jason Clarke , Elizabeth Debicki , Isla Fisher Runtime 143 Minutes

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.

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From undercover cops to deceitful conmen, Leonardo DiCaprio has played some of his best characters across his six Martin Scorsese movies.

16 American Psycho (2000)

Christian Bale In A Yuppie Horror Movie

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Based on the book of the same name by Bret Easton Ellis, American Psycho follows Patrick Bateman (Christian Bale) an investment banker in New York in 1987 who leads a double life as a serial killer. As investigators circle Bateman after the disappearance of a colleague, he finds himself trapped in a spiral of murder and excess, unable to stop himself from giving in to his increasingly dark urges. Also stars Willem Dafoe, Jared Leto, Justin Theroux, and Reese Witherspoon. 

Director Mary Harron Release Date April 13, 2000 Cast Jared Leto , Reese Witherspoon , Chloe Sevigny , Willem Dafoe , Justin Theroux , Christian Bale Runtime 101 minutes

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.

15 Boiler Room (2000)

A Crime Movie In A Brokerage Firm

Vin Diesel with his arms stretched out in Boiler Room

Boiler Room (2000) R

Boiler Room is a gripping drama set in the high-stakes world of underground stock trading. Giovanni Ribisi stars as Seth Davis, a college dropout who becomes entangled in an illegal brokerage firm that promises instant wealth but at a moral cost. The film explores themes of greed, corruption, and the pursuit of the American Dream, showcasing the consequences of unethical business practices.

Director Ben Younger Release Date February 18, 2000 Cast Giovanni Ribisi , Vin Diesel , Nicky Katt , Ben Affleck , Ron Rifkin Runtime 120 Minutes

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.

14 Glengarry Glen Ross (1992)

The Cut-Throat World Of Salesmen

Alec Baldwin giving a presentation with Always Be Closing written on the blackboard behind him in Glengarry Glen Ross

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Glengarry Glen Ross is a drama directed by James Foley, adapted from David Mamet’s Pulitzer Prize-winning play. The film stars Al Pacino, Jack Lemmon, Alec Baldwin, and Kevin Spacey, and centers on a group of real estate salesmen whose jobs are on the line as they compete in a high-stakes sales contest. The intense narrative unfolds as desperation and unethical tactics come to the forefront in the battle for survival.

Director James Foley Release Date October 2, 1992 Cast Al Pacino , Jack Lemmon , Alec Baldwin , Alan Arkin , Ed Harris Runtime 100 Minutes

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.

13 Goodfellas (1990)

A Martin Scorses Crime Movie Masterpiece

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Goodfellas is a 1990 crime film starring Robert De Niro, Joe Pesci, and Ray Liotta. The film was directed by Martin Scorsese and outlines the life and times of mobster Henry Hill. It’s based on the book Wiseguy, written by Nicholas Pileggi.

Director Martin Scorsese Release Date September 12, 1990 Cast Robert De Niro , Ray Liotta , Joe Pesci , Lorraine Bracco , Paul Sorvino , Frank Sivero Runtime 146 minutes

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.

12 War Dogs (2016)

Jonah Hill Stars In A Movie About Arms Trading

Jonah Hill wearing sunglasses in War Dogs

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In 2005, David’s life takes a turn when he joins his friend Efraim’s arms-dealing business to support his growing family. As they navigate risky deals and betrayals, David faces moral dilemmas and learns the true cost of their actions. With his loyalty tested and secrets exposed, David must confront his conscience amidst escalating tensions. The story culminates in a thrilling climax as David grapples with the consequences of his choices, leading to unexpected outcomes and a poignant resolution.

Director Todd Phillips Release Date August 19, 2016 Cast Jonah Hill , Shaun Toub , JB Blanc , Dan Bilzerian , Brenda Koo , Ana De Armas , Miles Teller , Barry Livingston , Bradley Cooper

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.

11 The Founder (2016)

The Man Who Created McDonald’s

Ray at the original McDonald's in The Founder

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In the 1950s, Ray Kroc discovers a revolutionary fast-food restaurant run by the McDonald brothers. Determined to turn their concept into a global empire, Kroc faces ethical dilemmas, power struggles, and personal sacrifices. As he navigates the complexities of business, relationships, and ambition, Kroc transforms McDonald’s into an iconic brand. With high stakes and unexpected twists, this gripping tale delves into the price of success and the true meaning of the American dream.

Director John Lee Hancock Release Date December 16, 2016 Runtime 115 Minutes Cast John Carroll Lynch , Nick Offerman , B.J. Novak , Steve Coulter , Laura Dern , Patrick Wilson , Michael Keaton , Linda Cardellini , Griff Furst , Kimberly Battista

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.

10 I, Tonya (2017)

Margot Robbie’s Tonya Harding Biopic

Margot Robbie on the ice in I Tonya

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Based on the life of figure skater Tonya Harding, I, Tonya chronicles Harding’s personal life, rise to fame, and subsequent downfall after her involvement in the infamous attack on her rival Nancy Kerrigan in 1994. Framed in a mockumentary style that routinely breaks the fourth wall, I, Tonya is directed by Craig Gillespie and stars Margot Robbie and Harding, with Sebastian Stan and Allison Janney as Harding’s ex-husband and overbearing mother respectively. 

Director Craig Gillespie Release Date December 8, 2017 Cast Julianne Nicholson , Allison Janney , Margot Robbie , Bobby Cannavale , Bojana Novakovic , Sebastian Stan , Caitlin Carver Runtime 120minutes

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.

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9 Wall Street (1987)

Oliver Stone’s Original Stock Broker Drama

Michael Douglas as Gordon Gekko behind desk in Wall Street

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In 1985, ambitious stockbroker Bud Fox seeks success under the mentorship of Wall Street mogul Gordon Gekko. As Bud climbs the ranks using insider information, he faces moral dilemmas and ethical compromises. When Gekko’s ruthless tactics threaten Bud’s values and his father’s livelihood, Bud orchestrates a daring plan to expose Gekko’s corruption. With high-stakes betrayals and moral reckonings, Bud navigates a world of wealth, power, and consequences.

Director Oliver Stone Release Date December 10, 1987 Cast Charlie Sheen , Tamara Tunie , Franklin Cover , Chuck Pfeiffer , John C. McGinley , Hal Holbrook Runtime 125 minutes

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.

8 Thank You For Smoking (2005)

Big Tobacco Lobbying The Government

Aaron Eckhart uses a lighter in Thank You For Smoking

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In Thank You For Smoking (2006), Nick Naylor, a charismatic tobacco lobbyist, navigates the challenges of promoting cigarettes while facing public scrutiny and personal conflicts. With wit and charm, Nick defends his industry against health advocates, politicians, and media attacks. As he balances ethics and loyalty, Nick confronts the consequences of his profession and discovers the true meaning of integrity. This satirical comedy offers a sharp commentary on media manipulation and moral ambiguity in modern society.

Director Jason Reitman Release Date March 17, 2006 Cast Joan Lunden , Eric Haberman , Aaron Eckhart , Mary Jo Smith , Todd Louiso , Jeff Witzke Runtime 92 minutes

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 mirrors 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.

7 The Aviator (2004)

Leonardo DiCaprio As Howard Hughes

Cate Blanchett and DiCaprio smiling at one another in The Aviator

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The Aviator is a 2004 biopic about Howard Hughes, a famous film producer, and pilot that was once considered one of the wealthiest and most influential men in the world. Directed by Martin Scorsese and written by John Logan, Leonardo DiCaprio stars as Hughes alongside Cate Blanchett, Kate Beckinsale, John C. Reilly, and Alec Baldwin.

Director Martin Scorsese Release Date December 25, 2004 Cast Willem Dafoe , Alan Alda , Leonardo DiCaprio , John C. Reilly , Alec Baldwin , Kate Beckinsale , Ian Holm , Cate Blanchett , Gwen Stefani , Jude Law Runtime 170 minutes

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.

6 Margin Call (2011)

A Movie About The 2007-2008 Financial Crisis

Zachary Quinto looks worried in Margin Call

Margin Call R Where to Watch

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In Margin Call (2011), an investment bank grapples with an impending financial crisis. When an analyst uncovers alarming data, the firm’s executives must make difficult decisions to save themselves and their company. As tensions rise and morality is tested, employees navigate the high-stakes world of finance where profit comes at a profound cost. This gripping drama sheds light on the complexities of Wall Street and the human toll of economic collapse.

Director J.C. Chandor Release Date February 11, 2011 Cast Kevin Spacey , Paul Bettany , Jeremy Irons , Zachary Quinto , Penn Badgley , Simon Baker Runtime 109 minutes

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.

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