From Inventing Anna to The Dropout – why Hollywood loves a scammer

Dramatisations and documentaries about scammers are taking over our streaming services. Laura Harding appraises the offerings.

What is it about scammers that we find so hard to resist? There is something about stories of con artists, swindlers and chancers that always keeps us coming back for more.

And Hollywood is getting in on the action, with some of the most high-profile scammers getting the small screen treatment with big-budget adaptations of their stories, starring famous faces.

The latest addition is Inventing Anna, the long-awaited drama series from Grey’s Anatomy creator Shonda Rhimes, based on the true story of “fake heiress” Anna Sorokin, played by Ozark star Julia Garner.

It is the first show Rhimes herself has written since she signed her blockbuster deal with Netflix (Rhimes is already the executive producer of Bridgerton, which is made by her company Shondaland).

Each episode begins with the following title card: “This whole story is completely true. Except for the parts that are completely made up.”

It follows Sorokin, a Russian-born German citizen, who went by the name Anna Delvey and posed as a wealthy German heiress in New York to scam banks and friends out of hundreds of thousands of dollars.

She claimed she had gone to the city to create the Anna Delvey Foundation, an artsy social club, and managed to insert herself into the New York social scene, rubbing shoulders with the movers and shakers of the city and convincing her wealthy new friends to foot her bills.

She racked up huge tabs at luxury hotels, where she managed to check in without leaving a credit card, she left friends thousands of dollars in debt as she foisted on them bills for high-end luxury trips, and she forged documents to defraud banks.

She was ultimately found guilty in 2019 of theft of services and grand larceny, having scammed more than 200,000 dollars (£145,000) from banks and luxury hotels.

She was sentenced to between four and 12 years in prison and served almost four (two in pre-trial detention) before she was released in February 2021 to much fanfare.

She launched a media blitz in New York, in which she appeared unrepentant for her crimes, but she was arrested again for overstaying her visa and remains in jail amid an appeal against deportation.

Soon arriving on Disney+ is The Dropout, based on the podcast of the same name, starring Amanda Seyfried as the Theranos founder Elizabeth Holmes.

Famed for her distinctive deep voice and black polo necks, Holmes convinced high-profile figures including media tycoon Rupert Murdoch and tech mogul Larry Ellison to invest in her start-up, claiming she had invented a pioneering blood testing machine, while former secretary of state Henry Kissinger and former defence secretary James Mattis sat on the board of the company.

The Stanford University dropout (hence the title) was hailed as “the next Steve Jobs” and “the world’s youngest self-made female billionaire” by business magazines, and Theranos was valued at nine billion dollars (£6.5 billion) for its Edison machine.

The machine could supposedly diagnose hundreds of medical conditions using just a few drops of blood, taken by pricking a finger.

The problem was, the machine did not work and Holmes’s recent trial heard of the lengths she went to to conceal this fact.

The dominoes started to fall after a Wall Street Journal investigation in 2015 found the company had only ever performed roughly a dozen of the hundreds of tests it offered using the device, and even those had questionable accuracy.

It turned out that Theranos was using devices made by other companies to run its tests and in 2018, Holmes and Theranos settled fraud charges with the Securities and Exchange Commission, but did not admit to or deny any of the allegations as part of the deal.

Last month Holmes was convicted by a jury in California of conspiracy to commit fraud against investors and three charges of wire fraud. She had denied the charges, which carry a maximum prison term of 20 years each.

During the trial, prosecutor Jeff Schenk told jurors that Holmes “chose fraud over business failure. She chose to be dishonest with investors and patients. That choice was not only callous, it was criminal”.

The show will cover the first series of the hit podcast, documenting the rise and fall of Holmes and her company, with Lost star Naveen Andrews playing her former business partner and ex-boyfriend Sunny Balwani, who is also facing criminal charges.

The second series of the podcast documented Holmes’ landmark trial, which ran for months, in detail.

These glitzy shows about scammers come hot on the heels of the hugely popular The Tinder Swindler, the first documentary to land at the top of Netflix’s weekly film viewing chart.

It exposes a fraudster posing as a jetsetting diamond mogul billionaire who lured women into his web of lies using the dating app and then conned them out of millions of dollars.

And who can forget the failed Fyre Festival – subject of the jaw-dropping Netflix documentary Fyre: The Greatest Part That Never Happened – where guests were promised luxury accommodation and deluxe food on an island in the Bahamas.

When they turned up they were told to sleep in tents used for disaster relief and offered meals of cheese slices on bread, and their luggage was thrown into a dark car park.

The event was billed as the “cultural experience of the decade” but turned out to be more like the holiday from hell.

Billy McFarland, who spearheaded the festival, is serving a six-year sentence after pleading guilty to multiple counts of wire fraud and bank fraud, but not before he became an internet sensation and the subject of countless memes.

It seems scammers will always hold an endless fascination, whether it is as cautionary tales, opportunities for voyeurism and maybe a bit of judgment of the people they duped, or just pure spectacle.

And as long as we are interested, the TV shows and documentaries will keep on coming, even if it is just to remind us to be cautious who we give our cash to.

Inventing Anna is streaming on Netflix now. The Dropout launches on Disney+ on March 3.