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 encom engaging crime and comedy.

25 Catch Me If You Can (2002)

Leonardo DiCaprio Con Movie

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

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 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

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

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

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 ing 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

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

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 , 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

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.

16 American Psycho (2000)

Christian Bale In A Yuppie Horror Movie

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.