The Wolf of Wall Street showcased Leonardo DiCaprio and Martin Scorsese at their best, and there are other great movies out there for fans to enjoy.
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 wasn’t just one of the best films of 2013, it was nothing short of a cultural phenomenon, spawning parodies, internet memes, and instantly quotable lines aplenty, and here are the best movies like Wolf of Wall Street. Martin Scorsese’s expletive-laden biographical crime comedy saga has become so much more than just a pop culture staple. The movie is 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 a number of movies to recommend from before and after the movie's release. From the 1960s to the modern time period, these are the best movies like Wolf of Wall Street that encompass engaging crime and comedy.
Moneyball (2011)
- Stream on Prime Video, Max, and Paramount+
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. The movie is significantly more uplifting than The Wolf of Wall Street and, on paper, 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.
Pain & Gain (2013)
- Stream on Paramount+
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 actually that smart, and it looks extremely stylish with its Florida setting. However, the main Pain & Gain characters exist solely to be laughed at, and there's no living vicariously through the crooks.
The Big Short (2015)
- Stream on Netflix
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. The Big Short has incredibly sharp wit and even an educational component. 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.
The Great Gatsby (2013)
- Rent on Apple TV
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.
American Psycho (2000)
- Stream on Peacock
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. American Psycho is full of murder and strange goings-on, and American Psycho ends completely open to interpretation, making it one of the best movies like Wolf of Wall Street.
Boiler Room (2000)
- Rent on Apple TV
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. Notable for featuring early standout supporting turns from Vin Diesel and Scott Caan as well as an appearance from Ben Affleck, Boiler Room is sharply written, well-paced, and worth checking out.
Glengarry Glen Ross (1992)
- Stream on Hulu
Adapted from David Mamet’s Pulitzer Prize-winning play of the same name, Glengarry Glen Ross might well be one of the most underrated movies of the 1990s. 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.
Goodfellas (1990)
- Stream on AMC
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.
War Dogs (2016)
- Stream on Hulu
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 go into partnership with him as an arms dealer. While things go to plan initially, the pair soon find themselves out of their depth after securing a $300 million deal to supply Afghan forces. Hill shines as the unreliable and increasingly unstable Efraim in what is only one of the many crime dramas and best movies like Wolf of Wall Street.
The Founder (2016)
- Stream on Tubi
A more subtle but no less powerful 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 might not have the same flashy approach or the colorful language of The Wolf of Wall Street, but it remains a fascinating exploration of the dark side of the American dream.
I, Tonya (2017)
- Stream on Max
Margot Robbie cemented her status as a bona fide A-lister with this Oscar-nominated turn as disgraced figure skater Tonya Harding. A warts-and-all black comedy chronicling one of the most infamous incidents in US sporting history when Harding allegedly schemed to have a rival taken out in the build-up to the Olympics, Robbie does a brilliant job of making the troubled skater a complicated, compelling, and strangely sympathetic character. Director Craig Gillespie also 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.
Wall Street (1987)
- Rent on Apple TV
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.
Thank You For Smoking (2005)
- Rent on Apple TV
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. Written and directed by Jason Reitman and based on Christopher Buckley’s 1994 novel of the same name, 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.
The Aviator (2004)
- Stream on Paramount+
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.
Margin Call (2011)
- Stream on Paramount+
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. An ensemble piece featuring fine turns from Zachary Quinto and Stanley Tucci, it’s Jeremy Irons who steals the show as one of the firm’s senior partners when he learns of the unfolding chaos.
The Social Network (2010)
- Stream on Paramount+
David Fincher took a look at 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 more chilling protagonist than DiCaprio's flamboyantly flawed Jordan Belfort.
The Death of Stalin (2017)
- Stream on Hulu
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.
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, and it should be of great interest to anyone captivated by Scorsese's use of beautiful actors in lewd circumstances. 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.
Casino (1995)
- Stream on Paramount+
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.
The Irishman (2019)
- Stream on Netflix
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, and 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.
