Hollywood Loves The Grift: Inventing Anna vs. The Dropout

Hello, everyone!

Americans love to watch narratives about con-artists, grifters, and scammers just as much as Hollywood loves to tell them. Too often, however, the victims in these stories fade behind the glamour of the con-artist themselves, and viewers are left with stories that can’t seem to tell the difference between exposing a scammer and glorifying them. Two such stories, Netflix’s series Inventing Anna, and Hulu’s series The Dropout, both dramatize the grifts of real people, but only one show manages to find the correct balance between telling a larger-than-life tale and remembering the little people at its center.

The show Inventing Anna is based off of the true story of Anna Sorokin, a Russian woman who pretended to be a German heiress and scammed hundreds of thousands of dollars in services and loans from hotels, restaurants, resorts, and banks. Told from the perspective of journalist Vivian Kent, a maligned reporter desperate to rescue her reputation, the show portrays Anna as a sensitive artistic soul who uses money as a way of keeping friends and whose $200,000 grift was merely a failed but ultimately good-natured attempt to establish herself in the world of New York’s elite. The show spends lots of time following Anna as she showers hotel employees and waiters with hundred-dollar tips and dreams about creating her Soho-House style social club The Anna Delvey Foundation. Through this lens, Anna comes across as a generous person with a vision of creating a haven for artists. Her only flaw it seems, according to the show, was that she was born poor, and forced to find creative sources of revenue to fund her dreams.

The show’s portrayal of Anna as a Robin Hood who steals from the rich and gives to the poor(er) hardly squares with the real Anna Sorokin’s documented history of behavior. The methods that she used to steal money, from pretending to be the manager of her fake trust fund, to sticking friends and acquaintances with her unpaid bills, demonstrate that she took advantage of others’ trust and general courtesy. She asked a friend to buy her a $3000 ticket to the Venice Biennale, then “forgot” to pay him back. She took another set of friends on an all-expenses-paid trip to a Moroccan resort, then ran away when it was time to pay, leaving one of the friends with a $60,000 credit card bill. Time and time again, Anna lied about her wealth to form connections with others, and let them pay the consequences for her actions. Rather than being a criminal mastermind, Sorokin was simply a manipulator; a person who used the unspoken rules of friendship and polite society to get what she wanted.

Perhaps the show lets Anna off the hook because she committed the majority of her fraud at fancy hotels and restaurants, or perhaps it’s because she made elite banking institutions look like fools, but either way, Inventing Anna finds it hard to blame Anna for anything. Instead, it relishes in her glamorous cons, giving her sassy one-liners and fabulous outfits to match her outlandish spending habits. In reality, however, Sorokin isn’t someone to aspire to. Acquaintances of Sorokin claim that she is “entitled and mean” and treated people in the service industry horribly, which is a far cry from her portrayal in the TV show. The fact is that Sorokin is a con-artist and a criminal. She committed grand larceny and put her friends into huge amounts of debt. The fact that she defrauded the wealthy doesn’t make her actions any less criminal. Sorokin has never shown any remorse, saying in 2019 that she’d “be lying to you and to everyone else and to myself if I said I was sorry for anything.”

But Inventing Anna doesn’t hold Sorokin accountable. Instead, it blames her victims, painting people like Rachel Williams, the friend who was made to pay Anna’s $60,000 resort bill, as greedy hanger-ons who only liked Anna for her money. The show makes a huge effort of painting Rachel as the bad guy in this scenario, acting as if she’s a person too naive and money hungry to deserve empathy, while giving the benefit of the doubt to Anna, even when her entire con was based around leeching off of other wealthy people. Why the show bends over backwards to excuse Anna’s actions is no secret. The very philosophy of the show is laid out in the trailer.

Image, money, power, everyone is hustling. Everyday, men do far worse things than I’ve allegedly done.

According to the show, we shouldn’t blame Anna for chasing the American dream and following the example of thousands of other rich people who “fake it ’till they make it.” The people who fell for her grift weren’t victims, they were simply incapable of competing in a free market. Anna isn’t a criminal; she’s a reflection of our society.

It’s so easy to let Anna off the hook. It’s harder, and scarier, to realize that she committed her crimes, not in the name of hustling, but in the name of self-interest and greed. If she’s a reflection of our society, then she’s a reflection of its worst decay.

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Compare Inventing Anna to The Dropout, and you get two series that are like night and day. While the former glorifies the antics of its subject, the latter investigates the systemic flaws that could allow someone to accumulate enough money and power to con others without consequences.

The Dropout tells the story of Elizabeth Holmes, the CEO of Theranos, a company that claimed to be able to test for hundreds of conditions with only a few drops of blood. Holmes managed to raise over $700 million in venture capital for her supposedly “revolutionary” company, only for it all to come crashing down when investigators discovered that the company had falsified its results and greatly exaggerated the capabilities of its technology.

The Dropout doesn’t shy away from portraying Holmes as a complex person. While the series depicts Holmes as a brainy and precocious undergrad with dreams of revolutionizing the health care system, it also shows her to be arrogant, uninformed, and obsessive; a person who is so determined to be the next Steve Jobs that she would lie, steal, and cheat her way to the top.

While Inventing Anna cloaks its protagonist in the shield of “girl-bossing,” The Dropout shows Holmes using her status as a female CEO to her advantage. She cries at a board meeting to gain sympathy from her detractors, and reels in investors by acting like a naive young girl in search of a father figure. The series wants its viewers to know that Holmes’ manipulation is a deliberate choice, and bolsters this by showing Holmes practicing different speeches in front of a mirror, or stealing a sob-story from an employee at the Apple Store. Holmes herself even says that she “doesn’t feel things like other people,” perhaps hinting at, if not psychopathy, then something close to it. Every choice Holmes makes, from faking test results to lying to investors, is portrayed as premeditated. The series avoids the mistakes of Inventing Anna by holding Holmes’ words accountable to her actions. The series could have easily let her off the hook by buying into Holmes’ own story of being a young and inexperienced CEO who accidentally defrauded investors, but instead The Dropout makes a point to show that Holmes’ fraudulent activity was not accidental, but instead a series of deliberate choices made for her personal gain.

The extent of Holmes’ fraud was much larger than Sorokin’s, so it makes sense that The Dropout feels more serious than Inventing Anna. But even though both grifters preyed on wealthy elites, The Dropout emphasizes the human cost of Holmes’ fraud by showing how her scamming hurt her employees, her family, and the patients who were involved in testing her products. The Dropout shows that large-scale fraud like Holmes’ can only take place on a systemic level, and that the blame lies with the system, not the victims of the fraud. Inventing Anna takes an opposite position, blaming Anna’s victims for their fraud by implying that it was their responsibility to protect themselves in the first place.

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Final thoughts: Inventing Anna is everything wrong with how Hollywood thinks of con-artists. It glorifies Sorokin’s exploits, blames her victims, and excuses her actions as symptoms of a fake it ’till you make it hustle culture. Conversely, The Dropout exemplifies the right way to discuss a scammer by showing how the actions of a self-interested con-artist can have destructive societal repercussions. Hollywood has a long history of making media in the vein of Inventing Anna, but I hope that The Dropout will show that it’s possible to tell a compelling story about a scammer without falling for their con.

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