The Dropout, Inventing Anna, and the Fascination with Female Fraudsters

Apr 15

They premiered less than a month apart.

Both boast A-list talent.

Both have topped the charts of their respective streaming platforms.

And both are about the most successful female con artists of our generation.

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Set in New York City, Inventing Anna dramatizes the true crime story of Anna Sorokin (or Anna Delvey, her alias), a woman in her twenties who posed as a German heiress and conned some of the city’s biggest hotels and banks into lending her huge sums of money.

On the opposite coast, set in Silicon Valley, The Dropout depicts the rise and fall of biotech protegé Elizabeth Holmes, who conned government officials, former secretaries of state, and even Walgreens into investing in a blood testing technology that never worked.

Though Inventing Anna premiered first, I actually watched the shows in reverse order, starting instead with The Dropout. Having followed the Elizabeth Holmes trial pretty closely, I was intrigued by a show that depicted her story, all the more so when I realized it featured the brilliant Amanda Seyfried. I wanted to see Hulu’s take on this horrific, unimaginable crime. As I tuned in religiously to each week’s episode, a friend suggested a similar show that she thought I would enjoy. “You like The Dropout?” she said, “Then you should definitely watch Inventing Anna.” I knew nothing about the Anna Sorokin case, so I didn’t realize I was going to watch a second show about a female fraudster. But once I noticed the connections between the shows, I began to wonder what it was about women con artists that audiences found so appealing.

To state what I would assume is the obvious, both Anna Sorokin and Elizabeth Holmes were completely aware of the financial fraud they were committing. Alongside the moguls they fooled, they also directly ruined the lives of ordinary individuals: Sorokin robbed her friend Rachel Williams of more than her annual salary and sent her plummeting into debt, while Holmes gave unreliable test results to patients with serious health issues. Yet, what is so quizzical about The Dropout and Inventing Anna is that both shows structure their narratives to shift the blame away from their protagonists. Elizabeth Holmes is just a pawn of her abusive boyfriend, Sunny Balwani. (In real life, while the courts sympathized with her suffering abuse, they did not find that it impacted her conscious decisions about her business.) Anna Sorokin is a product of New York City’s toxic, money-hungry culture; she’s a woman trying to make it in business, surrounded by men who won’t take her seriously if she doesn’t lie about her wealth.

Not only do the shows exonerate these women from their crimes, but audiences have readily eaten up their stories. Inventing Anna depicts the Sorokin fandom in the show itself, including in a scene where reporter Vivian Kent crosses paths with a stranger sporting a “Fake German Heiress” t-shirt. That scene is a pretty good representation of what has happened in real life, especially as a result of these two miniseries: Sorokin and Holmes have become cultural icons. One TV review even called 2022 “the year of the girlboss scammer.” Girlboss? In my book, these women are called criminals.

But the truth is that I, too, tuned in to watch their stories. I, too, was intrigued. Why?

Perhaps it lies in the fact that Anna Sorokin and Elizabeth Holmes had power, status, and impressive goals they wanted to achieve. The aesthetics of both shows highlight all the glitz and glamor that they had access to, like sleek offices, fancy dinners, businesspeople in suits… the list goes on. Beyond just the material aspects of their lives, these women were also listened to. In The Dropout, Holmes walks into a room and even the CEO of Walgreens shuts up and listens to her. Anna Delvey has the same command of every space she visits in Inventing Anna. Who doesn’t wish they had the power to silence a mean boss or stupid coworker with Delvey’s iconic line: “I do not have time for this, I do not have time for you!”

Perhaps, then, audiences have soaked up The Dropout and Inventing Anna because of the piece inside of them that craves seeing a woman in a position of power. I can’t blame them; I love seeing it too. But does our desire to see strong, independent women erase any shred of a moral compass that tells us when a woman’s actions are wrong?

It also remains puzzling that both The Dropout and Inventing Anna feature supporting female characters, also based on real-life people, who could have been hailed as the “girlbosses of 2022” but their respective shows did not let them. Erika Cheung, the courageous Theranos whistleblower who went on to build an institute for ethics in entrepreneurship, could have been the female role model of The Dropout. Rachel Williams, who turned trauma into triumph and, yes, wrote a book about her story that helped her get out of debt, could have been the superhero of Inventing Anna – the show manages to turn her into the villain instead. Vivian Kent, based on journalist Jessica Pressler who covered the Sorokin story, could have been the ultimate example of an empowered woman who wouldn’t let attacks from the press or impending childbirth stop her from being the journalist she wanted to be. But her arc in Inventing Anna ends with her questioning every decision she made, wondering if she was to blame for who Anna Sorokin became. Raising these supporting characters up as role models would have sent an inspiring message about women’s ability to persevere no matter what the world throws at them, including betrayal from their own friends and colleagues. Instead, their stories fell to the sidelines in order to make room for the supposed “heroes” that were Sorokin and Holmes.

I struggle to believe that the only female-centered stories that will bring in audiences are those about criminals. Yes, women want to see other powerful women on screen, but conflating that with female fraudsters is dangerous and undermines everything that women are capable of. Inventing Anna and The Dropout suggest that successful, powerful women are women who have lied and cheated their way to the top. With Anna Sorokin and Elizabeth Holmes as glorified TV examples, who’s to say that future women climbing the career ladder won’t be suspected of doing the same?