It took a little known production company, Red Granite, to take the gamble on such explicit material and come up with the $100m or so needed to bring the film to cinema screens.
Now that company has been swept up in a corruption investigation amid allegations that some of the money used to make the film was laundered from a scandal-hit Malaysian firm founded by the country's prime minister.
Najib Razak, Malaysia's prime minister, is at the centre of allegations that hundreds of millions of dollars were stolen from 1Malaysia Development Berhad (1MDB), a company that has racked up debts of $7 billion since it was founded.
Global investigators believe $155 million from 1MDB moved into Red Granite in 2012 through an intricate route involving offshore shell companies, according to sources cited by The Wall Street Journal.
FBI agents have issued subpoenas to several current and former Red Granite employees and to a bank and an accounting firm the company used.
One of the company's founders is Riza Aziz, the London-educated 39-year-old step-son of Mr Najib. The company denies any wrongdoing.
“Red Granite is responding to all inquiries and cooperating fully,” a spokesman for the company, based in West Hollywood, California, told the newspaper. He said it had no reason to believe there was anything suspect about the source of its financing.
The Wolf of Wall Street is based on the life of Jordan Belfort, who in the 1990s become a wealthy stockbroker living a life filled with sex and drugs by swindling investors in a securities scam. His firm was shut down in 1995 and Belfort was sentenced to four years in prison, of which he served 22 months.
He has since made a living as a motivational speaker.
DiCaprio won the rights to his memoir in 2007 but the project was shelved by Warner Bros before Red Granite stepped in.
The film was eventually released in 2013 and nominated for five Oscars, although it won none.
Ironically, it was never shown in Malaysia, where censors demanded more than 90 cuts to comply with local morality laws.
But the success of the film elsewhere established Red Granite as a force in Hollywood and it went on to produce Daddy’s Home, with Will Ferrell and Mark Wahlberg, among others.
For his part, Mr Najib denies any wrong doing and says he is the victim of a political conspiracy. He has struggled to explain how hundreds of millions of dollars ended up in his bank account, and initially denied receiving overseas payment.
However, his government later acknowledged that Mr Najib was the recipient of $681 million, saying it was a gift from the Saudi royal family - most of which was given back - to "promote moderate Islam". That explanation is yet to be confirmed by Saudi Arabia and is widely dismissed in Malaysia as a cover story.
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