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From ‘WeCrashed’ to ‘The Dropout,’ Why Is Grifter TV the Trend of the Moment?

There's now a desire to go beyond the headlines and show these characters in a way that feels authentic.

Amanda Seyfried

“The Dropout”

HULU

Editor’s Note: This post has been updated on April 6, 2022.

Grifters are littering the TV landscape. From Netflix’s “Inventing Anna” and true-crime documentaries “Bad Vegan” and “The Tinder Swindler,” to Hulu’s “The Dropout,” and Apple’s new series “WeCrashed,” audiences are flush for choice when it comes to the art of being bad. But what is it about grifters that is currently attracting us? It’s a soup as complicated as the characters we’re seeing.

This isn’t a particularly new trend; the conman, of course, is as American as apple pie. These shows generally depict not just a con, but the entitlement and ridiculousness of the rich. “WeCrashed” follows Adam and Rebekah Neumann (Jared Leto and Anne Hathaway, respectively), the founders of WeWork, as they blithely remain out of touch to things like equal pay and gender imbalances. “Inventing Anna,” Netflix’s buzzy retelling of the Anna Delvey story, sees leading lady Julia Garner wrap herself and her friends in expensive vacations and other trappings of sophistication. The audience is enthralled by seeing how much money can buy and how insular that world is. The women of these stories are generally presented as lonely, awkward, and desperate to please. The men confident, but entrenched in delusions of grandeur.

It’s reminiscent of the screwball comedies of the 1930s, a film genre heavily connected to the Great Depression. Screwball comedies often presented the wealthy as similarly out-of-touch and zany. It’s not that they don’t know what’s going on in the world, it’s that their wealth has allowed them to stay safely away from the rampant homeless and “forgotten men” who litter the streets. In the sharpest divergence between this era and our current one, screwball comedies often had a “real” character, usually a man, who was representative of the people who would corral and tame the (usually female) rich person. Some of these commonalities remain, like journalist Vivian Kent (Anna Chlumsky) slowly turning into Anna Delvey’s one friend in “Inventing Anna.” But more often than not these characters remain stuck in their bubble, not necessarily interested in being tamed or finding what’s real, but creating their own realities.

But why the uptick? There’s certainly a desire to capitalize on true stories, especially ones that would draw in the crime market. In a 2021 article on The Ringer, true-crime documentaries was cited as one of the biggest and fastest growing markets of documentary out there. Add to that continued economic disparity and political divide and the time has never been better for an exploration of how the rich and fake have been able to profit off the pain of others.

Julia Garner

“Inventing Anna”

NICOLE RIVELLI/NETFLIX

The characters assembled in this new wave of grifter television don’t fall cleanly into the realm of antiheroes, an oft-overused term that tends to encompass anyone from a flawed character to an outright villain. The show doesn’t necessarily want to glorify these characters’ crimes, but instead presents their exploits as over-the-top, proof of how the one percent lives. There’s a large amount of schadenfreude that comes from watching their inevitable downfall, particularly in a landscape where justice so often seems to evade the rich and powerful.

But with today’s grifter television shows there’s an added air of give and take, a desire to go beyond the headlines and show these characters in a way that feels authentic. Today’s audiences want the story behind the story. Entrepreneurs like the Neumanns and Theranos founder Elizabeth Holmes were perceived as revolutionaries at the time; Holmes, especially, ushered in the era of the “girlboss,” compelling women to start companies and be their own leaders. With the distance of time, these shows often believe there’s an ability to find nuance in their larger-than-life personas.

For Seyfried, the appeal comes from seeing people do the wrong thing and wonder if a different decision might have affected the outcome. “I am looking for a reason to want to believe in them,” Seyfried said to IndieWire. “I’m looking for hope. I’m looking for any sign that it’s not all or nothing, or that they’re not that bad.” Seyfried noted the act of watching television is for the audience to put themselves in a role and that narrative looks at grifters help teach the audience compassion.

“I wasn’t devastated when I listened to ‘The Dropout’ podcast,” Seyfried said. “I was like, ‘Good, she got what she deserved.'” But to actually see a narrative is to see how the main figure views themselves.

This might explain the give-and-take grifter shows are having with their main characters. “The Dropout” presents Holmes as both a swindler and also a young woman in a toxic and controlling relationship with her business partner, Sunny (Naveen Andrews). “WeCrashed” sells itself not strictly as the story of WeWork’s crash and burn, but the “love story” between its founders. Since “Inventing Anna” debuted, that series has received both criticism and praise for how it presents victim Rachel Williams as more of an opportunist than Delvey herself.

Jared Leto, Anne Hathaway

“WeCrashed”

Apple TV+

Garner said she certainly doesn’t believe Delvey is innocent but that much of the convicted conwoman’s actions seem motivated by a fear of failure. “She went to the nth degree…which ultimately didn’t work,” Garner told IndieWire when discussing the project. “But behind the fear of failure is the fear of rejection, and behind the fear of rejection is a person struggling with their identity.”

It’s hard not to see that somewhat, especially in works like “Inventing Anna” where all of Delvey’s friends are presented as eager to join the life of exotic trips and dinners to fancy restaurants. The characters peppering the current wave of grifter television have lost their high-powered positions or have seen criminal charges; Anna Delvey is set to be deported while Elizabeth Holmes could be sentenced to 20 years in jail this September. But the Neumanns still live in the lap of luxury, with a recent Forbes article listing Adam Neumann’s net work at $750 million. (Mr. Neumann has never been charged or indicted for fraud, although the New York District Attorney was investigating Neumann for self dealing shortly after he resigned as CEO in the face of pressure from his board and investors.) Simon Leviev, the alleged “Tinder Swindler” of Netflix’s doc, allegedly signed a deal with a Hollywood agent.

If anything, this stokes the fuel that many of these grifter series show the discrepancy of being a bad woman versus a bad man. Though it’s unclear whether this is justice as audiences have come to expect. The fact that none of these shows take a harsh stance on whether these characters are wrong or just flawed only continues to push the fact that, deep down, consumers enjoy being taken in. 

Seyfried said it feels poignant that many of these shows end with a downfall (regardless of where their real-life counterparts end up). “Comebacks aren’t as fun for some sadistic reason,” she said. Maybe because, unlike the screwball comedies of the 1930s, there’s little ability to feel good about watching a comeback from people who have hurt many. But that doesn’t stop us from pressing play on the next scam.

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