In the prologue to his 2007 book The Wolf of Wall Street, Jordan Belfort describes his first day as a trainee at the storied Wall Street firm LF Rothschild. From snorting cocaine during lunch to hiring prostitutes for a weekend getaway, it’s all in a day’s work for Wall Street high-fliers. The prologue ends on a more somber note, as Belfort promises to familiarise the reader with the “cautionary tale” of his unbridled success on Wall Street.

Belfort is the founder of Stratton Oakmont, which rode on the stock market boom in the early 1990s to defraud investors into buying penny stocks that had no long-term value. The firm was finally shut down in 1996 and securities fraud and money laundering charges were brought against Belfort and his associate Danny Porush in 1999. They served reduced prison sentences after cooperating with the authorities.

With this background and the earnestness of the prologue, one would imagine that Belfort’s book would be a serious attempt at redeeming himself. Unfortunately, the book’s tone indicates otherwise. Right from the first chapter, Belfort is keen to introduce the reader to the perks of the high life. His description of properties owned and collectibles gathered runs into many pages, inducing a mix of boredom and revulsion in the reader.

What’s worse, Belfort’s materialism extends to his description of the people in his life. Particularly galling is his description of Nadine, his second wife, who comes across as little more than a body hired for his pleasure. One scene has him describe his frustration at her decision to decline him sex after she discovers that he has been spending his nights with other women. The graphic, vulgar language leaves a bad taste.

It is fair to guess that Martin Scorsese was enthused by Belfort’s story since he wished to capture the changing nature of organised crime in America. For the man who gave us penetrating insights into the lives of drug lords and gangsters, the opportunity to capture Wall Street swindling must have been too delicious to pass.

Sadly, like the book, the 2013 film too does not leave an impact. It is a nearly faithful adaptation, with entire scenes and dialogue dutifully planted on the screen, but the whole refuses to become more than a sum of the parts. Leonardo DiCaprio plays Belfort and Jonah Hill plays Donnie Azoff, Belfort’s sidekick modelled on Porush. That’s the first of the film’s problems, with DiCaprio entirely miscast in the role.

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The Wolf of Wall Street (2013).

This comes through at several points in the film. The scene where he tries convincing Naomi (Margot Robbie playing Nadine) to have sex with him is surreal not merely for its inclusion in a Scorsese film but because DiCaprio is simply not our idea of a man who will be found in that sort of a situation. Even as the actor tries to carry it off with a vile mix of desire and obsequiousness, he is less than convincing.

In a later scene, DiCaprio is on the trading floor, introducing footwear expert Steve Madden to his employees. (Madden’s IPO was filed by Stratton Oakmont.) This scene is one of many in which DiCaprio evangelises for his lifestyle, pitting the “winners” against the “losers”, speaking ostentatiously about the advantages of being super-rich. The problem, again, is not so much the scene or DiCaprio’s hollow words as the fact that he delivers them.

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The Wolf of Wall Street (2013).

It is not that DiCaprio has not played the antihero before. In films such as Catch Me If You Can and Shutter Island, his character has shades of gray, but seldom has he played a part that does not have some emotional truth to it. In Catch Me If You Can, his swindling was built on an arc of utter, wholesome loneliness, and in Shutter Island, his villainy arose from psychosis. Such nuances do not operate in The Wolf of Wall Street.

This outcome springs from the turgidness of the book itself. Belfort would have had a real shot at making amends for his past if he had spoken about the ruined lives of those caught up in his skullduggery. But his book is entirely silent on his victims, the faux-tone of remorse towards the end masking his real regret: his inability to continue living the high life without getting caught.

The film maintains this tone, as it chronologically maps the dismantling of the cards that Belfort illegally stacked. This is one reason that, as I reached the end of the film, I began entertaining the idea that DiCaprio’s miscasting may have been a deliberate ploy by Scorsese.

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The Wolf of Wall Street (2013).

If the book’s flashiness is in danger of luring the gullible reader into believing that there is something to making illicit money, the film disabuses the viewer of any such notion. And it drives this point home by making DiCaprio the face of the systematic abuse of financial trust. At no point does the viewer connect with DiCaprio, because even at Belfort’s worst moments, the viewer cannot escape the feeling that the man on the screen is not DiCaprio but a soulless doppelganger.

To the reader of the book, this feeling reinforces the aversion engendered by the film. In its twisted way, then, the film is at least able to send out the message that Belfort purportedly hoped to convey through his book. It also saves the viewer from reading Belfort’s purple prose. That apart, the film has few compensating qualities. Other recent films, such as The Big Short, do a better job of educating viewers about what goes down on Wall Street. Scorsese’s tale of a stock trader’s rise and fall fails to be a triumph.

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Jordan Belfort.