Martin Scorsese’s 2013 biographical crime comedy The Wolf of Wall Street was a massive critical and commercial success, grossing nearly $400 million worldwide and earning five Academy Award nominations, including Best Picture. The film chronicles the wild rise and fall of real-life stockbroker Jordan Belfort, played by Leonardo DiCaprio in one of his most iconic roles. Belfort made a fortune in the 1990s through his brokerage firm Stratton Oakmont by defrauding investors and engaging in rampant corruption and illegal activity on Wall Street.
The Wolf of Wall Street is an exhilarating, hilarious, and at times disturbing look at the hedonistic excesses and unchecked greed that defined an era. It’s a film bursting with manic energy, Scorsese’s kinetic directing style, and unforgettable performances, especially from DiCaprio and Jonah Hill.
If you loved The Wolf of Wall Street and are craving more movies that capture a similar vibe – whether it’s the high-stakes world of finance, charismatic real-life con artists and criminals, or just the sheer audacious filmmaking style – then look no further. We’ve compiled the 21 best movies to watch next.
These films span many decades and genres but all share common DNA with Scorsese’s masterpiece. So get ready for more tales of ambition, excess, deception, and the high cost of the American Dream.
1. The Big Short (2015)
Directed by Adam McKay, The Big Short is a darkly comedic look at the events leading up to the 2007-2008 financial crisis. Based on the nonfiction book by Michael Lewis, the film follows a group of outsiders and misfits in the financial world who predicted the housing bubble and bet against the big banks, ultimately profiting from the economic meltdown.
With an all-star ensemble cast including Christian Bale, Steve Carell, Ryan Gosling, and Brad Pitt, The Big Short takes a complex subject and makes it both entertaining and infuriating, shining a light on the greed and fraud that nearly brought down the global economy. Like The Wolf of Wall Street, it’s a scathing indictment of unchecked capitalism and the culture of excess that permeated Wall Street in the early 21st century.
2. Margin Call (2011)
Set over a 24-hour period at the onset of the 2008 financial crisis, Margin Call is a tense, gripping thriller that takes viewers inside the walls of a powerful investment bank on the brink of disaster. When an entry-level analyst (Zachary Quinto) discovers information that could prove the firm’s downfall, a roller-coaster ride ensues as key players (Kevin Spacey, Paul Bettany, Jeremy Irons, Demi Moore) grapple with the moral and financial implications of their actions.
Written and directed by J.C. Chandor, Margin Call is a more sober and restrained film than The Wolf of Wall Street, but it shares its fascination with the high-stakes world of finance and the human toll of unchecked greed. With its stellar cast and taut storytelling, it’s a must-watch for anyone who enjoys smart, thought-provoking dramas.
3. Boiler Room (2000)
Boiler Room stars Giovanni Ribisi as Seth Davis, a college dropout who gets a job as a trainee stockbroker at J.T. Marlin, a shady brokerage firm that specializes in pump-and-dump schemes. As Seth gets caught up in the firm’s fast-paced, high-pressure culture of cold calls and hard sells, he begins to question the ethics of what he’s doing – especially as the FBI starts closing in.
Directed by Ben Younger, Boiler Room is a gritty, intense look at the underbelly of the stock market, with standout performances from Ribisi, Vin Diesel, and Ben Affleck. Like The Wolf of Wall Street, it’s a cautionary tale about the seductive power of easy money and the moral compromises that come with it.
4. Wall Street (1987)
Oliver Stone’s Wall Street is the quintessential film about 1980s excess and the cutthroat world of finance. Charlie Sheen stars as Bud Fox, an ambitious young stockbroker who falls under the sway of Gordon Gekko (Michael Douglas), a ruthless corporate raider who will stop at nothing to get what he wants.
As Bud rises through the ranks and enjoys the spoils of his newfound wealth, he begins to question the morality of Gekko’s “greed is good” ethos – especially as he sees the human cost of his mentor’s actions. With sharp writing, iconic performances, and a still-relevant message about the dangers of unchecked capitalism, Wall Street remains a classic of the genre.
5. Glengarry Glen Ross (1992)
Based on David Mamet’s Pulitzer Prize-winning play, Glengarry Glen Ross is a blistering look at the cutthroat world of real estate sales. Set over two days in a small Chicago office, the film follows a group of desperate salesmen (Al Pacino, Jack Lemmon, Ed Harris, Alan Arkin) as they compete to keep their jobs by any means necessary – including lying, cheating, and stealing.
Directed by James Foley and featuring an all-star cast, Glengarry Glen Ross is a masterclass in acting and dialogue, with Mamet’s razor-sharp script cutting to the bone of the American Dream. Like The Wolf of Wall Street, it’s a searing indictment of a system that rewards ruthlessness and punishes weakness.
6. American Psycho (2000)
Based on the controversial novel by Bret Easton Ellis, American Psycho stars Christian Bale as Patrick Bateman, a wealthy investment banker by day and a sadistic serial killer by night. Set in the excess and materialism of 1980s New York City, the film is a pitch-black satire of yuppie culture and the soulless pursuit of status and wealth.
Directed by Mary Harron, American Psycho is a stylish, darkly comedic thriller that skewers the same culture of greed and narcissism that The Wolf of Wall Street depicts. Bale’s chilling performance as Bateman is a standout, capturing the character’s superficial charm and deep-seated psychosis.
7. Catch Me If You Can (2002)
Directed by Steven Spielberg, Catch Me If You Can tells the true story of Frank Abagnale Jr. (Leonardo DiCaprio), a teenage con artist who successfully posed as a pilot, doctor, and lawyer while cashing millions of dollars in fraudulent checks. Tom Hanks co-stars as Carl Hanratty, the dogged FBI agent who pursues Frank across the country.
Like The Wolf of Wall Street, Catch Me If You Can is a stylish, fast-paced caper that revels in its protagonist’s audacity and charm, even as it acknowledges the damage he leaves in his wake. DiCaprio’s performance is a tour de force, capturing Frank’s intelligence, charisma, and ultimate emptiness.
8. The Founder (2016)
The Founder stars Michael Keaton as Ray Kroc, the ambitious salesman who turned a small hamburger stand called McDonald’s into a global fast-food empire. Directed by John Lee Hancock, the film chronicles Kroc’s ruthless rise to power, as he wrests control of the company from its founders and builds an empire on the backs of franchisees.
Like Jordan Belfort in The Wolf of Wall Street, Ray Kroc is a man consumed by his own ambition, willing to do whatever it takes to succeed. Keaton’s performance captures both Kroc’s charm and his darkness, making him a fascinating and complex protagonist.
9. Molly’s Game (2017)
Written and directed by Aaron Sorkin, Molly’s Game tells the true story of Molly Bloom (Jessica Chastain), a former Olympic-class skier who ran one of the world’s most exclusive high-stakes poker games for Hollywood celebrities, business tycoons, and the Russian mob. When she becomes the target of an FBI investigation, Molly must fight to clear her name and rebuild her life.
Like The Wolf of Wall Street, Molly’s Game is a fast-paced, adrenaline-fueled look at a world of wealth, power, and excess. Chastain delivers a powerhouse performance as Molly, capturing her intelligence, toughness, and vulnerability.
10. The Gambler (2014)
A remake of the 1974 film of the same name, The Gambler stars Mark Wahlberg as Jim Bennett, a literature professor with a serious gambling addiction. As his debts mount and his life spirals out of control, Jim must confront his demons and find a way out before it’s too late.
Directed by Rupert Wyatt, The Gambler is a gritty, intense look at the seductive power of risk and the destructive nature of addiction. Wahlberg delivers a raw, vulnerable performance as Jim, capturing the character’s desperation and self-loathing.
11. Arbitrage (2012)
Arbitrage stars Richard Gere as Robert Miller, a wealthy hedge fund magnate who seems to have it all – a loving family, a successful business, and a lavish lifestyle. But when a deadly accident threatens to expose his fraudulent dealings and destroy everything he’s built, Robert must navigate a web of lies and betrayal to stay one step ahead of the law.
Directed by Nicholas Jarecki, Arbitrage is a taut, suspenseful thriller that explores the corrupting influence of power and wealth. Gere delivers one of his best performances as Robert, a man whose charm and confidence mask a deep-seated sense of entitlement and amorality.
12. The Company Men (2010)
Set against the backdrop of the 2008 financial crisis, The Company Men follows three corporate executives (Ben Affleck, Chris Cooper, Tommy Lee Jones) as they struggle to rebuild their lives after losing their jobs in a round of downsizing. As they grapple with issues of identity, purpose, and self-worth, the film offers a poignant commentary on the human cost of corporate greed and the fragility of the American Dream.
Directed by John Wells, The Company Men is a more somber and introspective film than The Wolf of Wall Street, but it shares its fascination with the culture of wealth and success that defines so much of American life. With strong performances from its cast and a thoughtful script, it’s a moving and thought-provoking drama.
13. Rogue Trader (1999)
Based on the true story of Nick Leeson, the British trader whose fraudulent dealings brought down Barings Bank in the 1990s, Rogue Trader stars Ewan McGregor as Leeson, a young man whose ambition and hubris lead him down a path of destruction. As he takes increasingly risky bets in the Singapore stock market, Leeson digs himself deeper and deeper into a hole, ultimately causing the collapse of one of Britain’s oldest and most respected financial institutions.
Directed by James Dearden, Rogue Trader is a cautionary tale about the dangers of unchecked greed and the consequences of taking shortcuts to success. McGregor delivers a compelling performance as Leeson, capturing both his charm and his desperation as he tries to cover up his mounting losses.
14. Owning Mahowny (2003)
Based on the true story of Canadian bank manager Brian Molony, who embezzled millions of dollars to feed his gambling addiction, Owning Mahowny stars Philip Seymour Hoffman as Dan Mahowny, a mild-mannered banker with a secret double life. As his gambling debts mount and his schemes become more desperate, Dan risks everything – his job, his marriage, and his freedom – to chase the next big win.
Directed by Richard Kwietniowski, Owning Mahowny is a quiet, understated film that nonetheless packs a powerful punch. Hoffman delivers a masterful performance as Dan, capturing the character’s inner turmoil and the seductive power of his addiction.
15. Enron: The Smartest Guys in the Room (2005)
A documentary rather than a narrative film, Enron: The Smartest Guys in the Room nonetheless shares many of the themes and concerns of The Wolf of Wall Street. Directed by Alex Gibney and based on the book of the same name, the film chronicles the rise and fall of Enron, the Houston-based energy company whose fraudulent accounting practices and rampant corruption led to one of the biggest corporate scandals in American history.
Through interviews with former employees, executives, and whistleblowers, as well as extensive archival footage, the film paints a damning portrait of a company culture that rewarded greed, deception, and hubris at the expense of ethics and accountability. It’s a chilling reminder of the human cost of unchecked corporate power and the importance of oversight and regulation in the financial world.
16. The Wizard of Lies (2017)
Directed by Barry Levinson and starring Robert De Niro as Bernie Madoff, The Wizard of Lies is a HBO film that chronicles the downfall of the infamous financier whose Ponzi scheme defrauded investors of billions of dollars. The film focuses on the aftermath of Madoff’s arrest and the impact of his crimes on his family, particularly his wife Ruth (Michelle Pfeiffer) and sons Mark and Andrew.
Like The Wolf of Wall Street, The Wizard of Lies is a portrait of a man consumed by greed and hubris, willing to destroy everything and everyone around him in pursuit of wealth and power. De Niro delivers a chilling performance as Madoff, capturing both his charm and his sociopathic detachment, while Pfeiffer brings depth and nuance to the role of Ruth, a woman struggling to come to terms with her husband’s betrayal.
17. 99 Homes (2014)
Set against the backdrop of the 2008 housing crisis, 99 Homes stars Andrew Garfield as Dennis Nash, a struggling single father who is evicted from his home by a ruthless real estate broker named Rick Carver (Michael Shannon). Desperate to provide for his family, Dennis begins working for Rick, learning the tricks of the trade and becoming complicit in the very system that destroyed his life.
Directed by Ramin Bahrani, 99 Homes is a powerful and provocative film that explores the human cost of the financial crisis and the moral compromises that people make in the face of economic hardship. Garfield and Shannon deliver intense, riveting performances, capturing the complex dynamic between their characters and the larger forces at play in the housing market.
18. Billionaire Boys Club (2018)
Based on the true story of the Billionaire Boys Club, a group of wealthy young men who ran a Ponzi scheme in 1980s Los Angeles, Billionaire Boys Club stars Ansel Elgort as Joe Hunt, the charismatic leader of the group, and Taron Egerton as Dean Karny, his right-hand man. As their scheme unravels and the authorities close in, Joe and Dean resort to increasingly desperate measures to maintain their lavish lifestyle and keep their investors at bay.
Directed by James Cox, Billionaire Boys Club is a stylish and fast-paced film that captures the excess and hedonism of the 1980s, as well as the dark underbelly of the American Dream. Elgort and Egerton deliver strong performances, capturing the charm and the menace of their characters, while Kevin Spacey (in one of his final roles before his fall from grace) brings a sense of gravitas to the film as Ron Levin, the con artist who becomes the Boys Club’s ultimate mark.
19. Goodfellas (1990)
Another Martin Scorsese classic, Goodfellas is the obvious choice if you’re seeking more of the director’s signature style and flair for depicting the lives of charismatic criminals. Like The Wolf of Wall Street, it’s based on a true story and stars Ray Liotta as Henry Hill, a former member of the Lucchese crime family who recounts his life in the mob.
With an all-star ensemble including Robert De Niro, Joe Pesci, and Lorraine Bracco, Goodfellas is a kinetic, violent, darkly funny look at life in the mafia. It features Scorsese’s trademark use of voiceover narration, pop music, and bravura camerawork, including the famous Copacabana tracking shot. Pesci won an Oscar for his unforgettable performance as the volatile Tommy DeVito.
20. American Hustle (2013)
David O. Russell’s American Hustle is another film that feels very much in the Scorsese mold, with its 1970s setting, ensemble cast, and freewheeling directing style. Christian Bale and Amy Adams star as Irving Rosenfeld and Sydney Prosser, a pair of con artists forced to work with an FBI agent (Bradley Cooper) to entrap corrupt politicians, including the mayor of Camden, New Jersey (Jeremy Renner).
Like The Wolf of Wall Street, it’s a stylish and darkly comic look at real-life events, in this case the FBI’s ABSCAM sting operation. The period details are impeccable, from the costumes to the hairstyles to the soundtrack. And the performances are fantastic across the board, especially Jennifer Lawrence, who earned an Oscar nomination for her supporting turn as Irving’s unpredictable wife Rosalyn.
21. American Made (2017)
American Made is a wild, entertaining ride based on the true story of Barry Seal, a former commercial airline pilot who became a drug smuggler for the Medellín Cartel in the 1980s before being recruited by the DEA to provide intelligence. Tom Cruise stars as Seal, bringing his trademark charisma and intensity to the role. Directed by Doug Liman, who previously worked with Cruise on Edge of Tomorrow, the film is a fast-paced, darkly comic look at the absurdity of the war on drugs and the CIA’s involvement in the cocaine trade.
Like The Wolf of Wall Street, American Made revels in the excesses and debauchery of its protagonist’s lifestyle, from the piles of cash to the exotic locales to the wild parties. But it also doesn’t shy away from the darker aspects of Seal’s story, including his eventual downfall and the toll his actions took on his family. If you’re a fan of Cruise or just love a good crime caper based on a true story, American Made is definitely worth checking out.
Conclusion
These 21 films capture the essence of what made The Wolf of Wall Street such a captivating cinematic experience. From the rise-and-fall narratives of Goodfellas and Boogie Nights to the exposés of corporate greed in The Insider and The Big Short, these movies offer a fascinating look at the dark side of the American Dream. Whether you’re drawn to the glitz and glamour of Casino and The Aviator or the gritty realism of Boiler Room and Glengarry Glen Ross, there’s something on this list for every fan of Scorsese’s masterpiece.
So grab some popcorn, settle in, and prepare to be transported into worlds of ambition, excess, and the high cost of chasing fortune and fame. These films may not have the same comedic energy as The Wolf of Wall Street, but they all share its unflinching look at the lengths people will go to achieve their dreams – and the consequences that come with living life in the fast lane.
