15 Best Movies Like The Wolf Of Wall Street

Martin Scorsese’s film, “The Wolf of Wall Street,” narrates the story of Jordan Belfort, a character portrayed by Leonardo DiCaprio, who accumulated wealth and faced imprisonment due to his questionable dealings in the stock market. The movie garnered DiCaprio his third Academy Award nomination for Best Actor, alongside Scorsese’s seventh nomination for Best Director. Notably, this R-rated film was a commercial success, ranking among the highest-grossing controversial films ever made.

When seeking films similar to “The Wolf of Wall Street,” it’s logical to explore movies centered around the stock market. However, “The Wolf of Wall Street” isn’t just about financial dealings; it delves into stories of individuals amassing wealth through unscrupulous means, deceiving others, and hiding questionable actions behind a friendly facade. It also explores the belief that money can resolve all issues and is the ultimate indicator of social standing.

In this list, we suggest movies that meet some or even all of these requirements, as well as another movie by Martin Scorsese, but perhaps not the one you’re expecting.

Wall Street

1987’s “Wall Street” is a top pick for fans of “The Wolf of Wall Street,” not just due to their similar subgenre, but because Jordan Belfort himself has acknowledged its significant influence. In his words, Belfort admired the main character, Gordon Gekko, portrayed by Michael Douglas in “Wall Street,” and aspired to follow a career path like Gordon’s — even though it seems he missed the part where Gordon eventually ended up in jail.

Despite some people having an overvalued admiration for Gordon Gekko, “Wall Street” is still a must-watch for anyone with a passing interest in stock trading and corporate finance. Michael Douglas won his only acting Oscar for his role as Gordon Gekko, a corporate raider who takes on the young stockbroker Bud Fox (played by Charlie Sheen) as an apprentice. At first, Bud appreciates the benefits of wealth and power that Gordon shows him how to wield, but when they have a falling out, it’s a battle between loyalty and self-preservation.

Casino

Instead of suggesting “Goodfellas” as a typical follow-up to “The Wolf of Wall Street” by Martin Scorsese, we suggest going with “Casino,” his less celebrated 1995 crime drama, for a more fitting Scorsese double feature.

One key similarity is that “Casino” primarily focuses on business matters, making it thematically consistent. Additionally, it’s based on a true story and follows a Chicago gangster named Sam Rothstein (portrayed by Robert De Niro). He’s tasked with revitalizing a struggling casino in Las Vegas. With the help of his childhood friend Nicky Santoro (Joe Pesci), he manages to turn things around using methods that aren’t always legal. Initially, everything goes well, but as the assignment becomes more challenging and complex, it starts to strain Sam both in his professional and personal life.

Beyond being among the top Las Vegas-themed movies, the film “Casino” is considered one of Martin Scorsese’s lesser-known masterpieces, often overshadowed by “Goodfellas”. However, it merits greater recognition and could be seen as a superior counterpart to “The Wolf of Wall Street”.

The Big Short

Numerous movies, TV programs, documentaries, and books have delved into the 2008 financial crisis, a topic that wasn’t typically light-hearted due to its grim nature. However, the 2015 film “The Big Short,” directed and co-written by Adam McKay, introduces humor to keep viewers engaged while still portraying the gravity of the crisis’s impact without sugarcoating it.

Gathering a powerhouse ensemble featuring Christian Bale, Steve Carell, Ryan Gosling, Melissa Leo, and Brad Pitt, McKay combined three pivotal events that unfolded in the years preceding 2008. The film portrays charismatic figures in suits peddling their goods and ideas, with some consciously embodying the role of charlatans while others did so seemingly unaware. It also showcases individuals who recognized the impending cracks, but whose warnings were largely disregarded or suppressed by those who stood to gain financially from the devastation they were poised to inflict on millions of American citizens.

Uncut Gems

Though Adam Sandler had previously garnered acclaim for his moving performances in films such as “Punch-Drunk Love,” “Reign Over Me,” and “The Meyerowitz Stories (New & Selected),” many were taken aback by the remarkable acting displayed in “Uncut Gems.” This performance netted him an Independent Spirit Award and a significant number of voices advocating that he was wrongly overlooked for an Oscar nomination.

In “Uncut Gems,” Sandler delivers an exceptional performance, and the film features a death-defying stunt, all while offering a gripping portrayal of the same persuasive, fast-paced, macho hustling that Jordan Belfort employed to amass his fortune. However, it’s not just about jewelry and precious stones; this time, the setting is different. The film gives us a glimpse into Howard Ratner’s life, who, like Belfort, seems to have triumphed over the system and has all the pieces in place for a well-deserved break. Yet, victory isn’t enough for Howard – he keeps chasing that elusive next big win, that “last” score, even though it’s his addiction to the excitement of the chase that truly drives him, not the actual attainment of success.

Money Monster

In the 2010s, numerous films explored the struggling economy, one of which was “Money Monster” from 2016, featuring George Clooney and Julia Roberts. However, it didn’t receive much attention when it was released. In this film, Clooney plays a host of a financial advice show who is held hostage by a disgruntled viewer (Jack O’Connell), whose life was negatively impacted by the show’s suspect investment advice. The entire broadcasting station becomes entangled in this dramatic situation.

In summary, while “Money Monster” received mixed reviews regarding its ending, critics appreciated the acting and writing. The film stands out because it presents a well-known story from an uncommon perspective, focusing on revenge rather than mere sadness and financial ruin. Although seeking revenge in real life is not advisable, especially if it’s illegal, it makes for an entertaining plot twist in this movie where no one gets physically harmed.

Maddman: The Steve Madden Story

In January 2025, news broke that a genuine documentary about Jordan Belfort and his troubled brokerage firm was under development. This will mark the first full-length documentary on both Belfort and Stratton Oakmont since previous documentaries only consisted of episodes from docuseries and YouTube videos. Once released, it’s highly likely to rank high among recommendations for viewing either before or after “The Wolf of Wall Street.

For those who have watched “The Wolf of Wall Street,” it’s worth noting that before then, a film most closely associated with the world of Belfort and Stratton Oakmont is the 2017 documentary “Maddman: The Steve Madden Story.” Steve Madden, famous for his luxury shoe, handbag, and accessory line, as well as his past legal troubles involving fraud and stock manipulation, has connections to Stratton Oakmont. This company was co-founded by one of Madden’s childhood friends. Interestingly, Madden himself appears in the movie, portrayed by actor Jake Hoffman.

Margin Call

For an entertaining take on the 2008 financial crisis, I’d recommend watching “The Big Short,” which features some of Hollywood’s most charismatic actors. If you prefer a more serious and informative approach, consider watching “Margin Call.” Together, they make for an engaging double feature, offering distinct perspectives on the same event while maintaining significantly different atmospheres.

Some might contend that an event which left lasting devastation on countless lives, with many still grappling to recover even two decades later, ought not be presented casually. For those who have been deeply affected, the film “Margin Call” would resonate more profoundly as it deals with a financial firm confronting news of an impending crash, set to occur the very next day. This leaves key figures at the company grappling with a moral dilemma: those advocating for actions that benefit the greater good versus those primarily concerned with minimizing personal losses and protecting their own livelihoods.

American Psycho

Despite the debate over its notorious ending often eclipsing its overall impact, there’s no disputing that “American Psycho” holds classic status, particularly among those who find figures like Jordan Belfort ripe for satire. In this film, Christian Bale portrays Patrick Bateman, a prosperous banker who appears to lead an enviable life. However, he also has a dark secret: he brutally murders individuals without any apparent remorse.

In terms of dark humor, “American Psycho” stands out as one of the bleakest, and not everyone may find it suitable. Although audiences who found “The Wolf of Wall Street” acceptable due to its excessive profanity and numerous nudity scenes might still feel uncomfortable with some of Patrick’s actions, the true comparison lies in their underlying messages. Some viewers may mistakenly admire the protagonists in “The Wolf of Wall Street,” despite the filmmakers’ intentions. However, “American Psycho” makes it clear within the first half that any approval is unwarranted and undesirable.

Trading Places

For a change of pace, let’s explore a cheerful comedy that humorously delves into the contrast between how the stock market and wealth operate differently for the affluent compared to everyday people. After watching intense films such as “The Wolf of Wall Street,” viewers seeking a lighter take on financial humor may find “Trading Places” refreshing, since it lacks the gruesome elements often found in similar movies.

Louis Winthorpe III (portrayed by Dan Aykroyd) and Billy Ray Valentine (Eddie Murphy) are a director of an investment firm and a swindler, respectively, who find themselves in completely contrasting situations. They become unwitting participants in a wager between two wealthy men, leading to a reversal of their roles, somewhat like a prince and a pauper. This experiment seems to validate the notion that wealth tends to accumulate among the rich while the less affluent struggle, but it’s also an entertaining journey and a timeless comedy – earning its status as a classic for good reason. In recent years, Reddit even named “Trading Places” as their unofficial favorite Christmas movie.

The 25th Hour

As a gaming enthusiast, let me say that while there’s a Wall Street trader character in Spike Lee’s “The 25th Hour,” it’s not just that reason that makes me recommend this movie to fans of “The Wolf of Wall Street.” Instead, the main focus is on the protagonist Monty, played by Edward Norton. He’s a drug dealer about to start a prison sentence, and the story unfolds over his last day of freedom. The film alternates between Monty trying to spend time with friends and loved ones before he goes in, and the incidents that led up to his initial arrest.

In a straightforward manner: It’s understandable that Monty doesn’t elicit much sympathy when he experiences consequences that are deserved. Frank appears to share this sentiment, although he never shows it directly to Monty. The individuals around Monty, however, exhibit some internal conflict about the justice of his punishment and whether or not he actually deserves it based on moral principles. “The 25th Hour” and “The Wolf of Wall Street” provide different perspectives on a criminal facing retribution, making them excellent pairings for viewing.

Dumb Money

A more contemporary film titled “Dumb Money” portrays the intricate and volatile realm of stock trading, with its dramatic events unfolding during the COVID-19 pandemic in 2020. The story revolves around a live streamer who heavily invests in the struggling Gamestop stock.

The leader persuades his supporters to act similarly, and what unfolds is a tale that demonstrates the unpredictable nature of stock values, how easily they can be influenced by powerful individuals, and how swiftly those same influential figures can reverse their fortunes – at the expense of ordinary people – whenever they choose. In the end, not every favorite character emerges victorious, nor does every adversary suffer defeat, but it remains a compelling narrative that underscores the fact that everyday people can sometimes outsmart Wall Street.

The Founder

1954 marks the year when Ray Kroc, a milkshake machine salesman, pays a visit to a Californian restaurant named McDonald’s, which had an unusual number of his machines. Upon arrival, he discovers an operation that strikes a balance between speed, efficiency, and quality service, comparable to other burger joints. It doesn’t take much time before Kroc manages to secure a partnership in the business through persuasion, ultimately assuming full control and leaving the original McDonald’s founders with minimal returns despite their crucial role in building a global fast-food empire.

In “The Founder,” Michael Keaton portrays Ray Kroc, a man who seizes control of an empire built by others – an enterprise he didn’t initially establish himself. This film stirs intense emotions, as it shows how one can manipulate their way to wealth, while marginalizing the very people responsible for their success. It is a must-watch for those with any curiosity about 20th-century business dynamics and entrepreneurship.

Boiler Room

As a fervent enthusiast of “The Wolf of Wall Street”, let me highly recommend the 2000 film “Boiler Room”. Jordan Belfort himself has hinted at its connection to his life, although the makers of “Boiler Room” have neither confirmed nor denied this claim. Regardless, the striking resemblance between the stories and the timing of “Boiler Room’s” release shortly after Belfort’s downfall makes it reasonable to draw a parallel.

Boiler Room” portrays the story of Seth (Giovanni Ribisi), who has skillfully created a thriving illegal gambling den within his home. When his stockbroker cousin introduces one of his associates to Seth’s hidden enterprise, they are taken aback by his achievements and extend an invitation for him to join their firm. Believing this to be an opportunity to apply his interpersonal skills and business savvy in a legitimate profession, Seth accepts the offer, only to discover that the company is far from ethical. Unwillingly, he becomes embroiled in an illicit venture that surpasses the illegality of his home gambling den.

Moneyball

As a gamer, I’d rephrase it like this: Not all folks juggling funds to tackle an issue are driven by selfish desires or intent on deceiving everyone. This notion resonates with the tale of “Moneyball,” centering around the man who masterminded the Oakland A’s resurgence in their 2002 season, not by splashing cash on potential superstars but by leveraging stats and math. Now, while “Moneyball” didn’t always stick to the facts, it provides a captivating glimpse into how raw intellect can outsmart conventional thinking in professional sports realms.

In the film “Moneyball”, none of the characters are like Jordan Belfort. To put it simply, while Billy Beane (played by Brad Pitt) may appear to be as invested in disproving his critics as he is in helping the A’s team succeed, ultimately, his actions serve a greater purpose beyond himself. The movie showcases once again how skillful manipulation of statistics can lead to victory.

Glengarry Glen Ross

Despite not being set in the stock market or Wall Street, ‘Glengarry Glen Ross’ is just as much a classic portrayal of intense salesman competition as ‘Wall Street’, if not more so. This compelling movie by David Mamet is based on his Pulitzer Prize-winning play and follows a team of real estate agents struggling to keep their jobs in a limited timeframe, pushing each other to the limit.

Without a doubt, this film brings out the most unscrupulous behavior in almost everyone, as they resort to every underhanded tactic imaginable – undermining, betraying, and sabotaging their peers just for personal gain. While only Al Pacino received an Oscar nomination, the movie serves as a testament to the exceptional acting skills of all involved, including heavyweights like Alec Baldwin, Jack Lemmon, Ed Harris, Alan Arkin, and Kevin Spacey, who delivered some of their finest performances ever. “Glengarry Glen Ross” is a film that film enthusiasts in general should watch, regardless of whether they’re seeking similar movies within a specific genre.

2025-06-21 04:31