Experts Explain Why You’re So Addicted To Scammer Stories

by Trish Bendix
Metro Goldwyn Mayer Pictures

In Ocean's 8, audiences were rooting for Sandra Bullock, Cate Blanchett and the rest of their crew to sneak into the Met Gala and retrieve their rightful (stolen) diamonds. In The Hustle, out May 10, we're likely to feel similarly about Anne Hathaway and Rebel Wilson's characters — con women hustling men who easily fall for their tricks because of their own gender bias. When it comes to real-life scam stories, however, our sympathies are usually with the victims. But why are we so fascinated by grifters and scammer stories in the first place?

Take, for instance, the endless discourse and countless memes about Fyre Festival, the luxury music event that was meant to take place in the Bahamas in 2017 but crashed and burned when it turned out that organizers had way overpromised on almost everything. There was only one failed attempt, but now the name of the disastrous music festival has become synonymous with scams and sh*tshows. Recently, a Jewish weekend retreat was coined "Passyover Fyre Fest" by Forward, who reported that hundreds of people were left stranded in Florida when organizers couldn't pay for goods and services. In Virginia, the rescheduling of the 2019 Nova Mac and Cheese Festival had one customer saying "I feel like this is the new 'Fyre Festival,'" which WLJA quickly spun into a headline.

Fyre Festival has become part of the lexicon in a major way thanks to its presence on social media and the two documentaries delving into the specificities of its demise. But its continued popularity is largely due to America's fascination with the monied attendees who were enticed into buying into a "luxury" experience that became a nightmare. Those of us who hadn't committed to going watched the fallout both in real time and later on screen, doing our own continued research and following threads on the specific parts of the scamming that were of interest. The public was, perhaps, looking for clues as to how this could have happened in the age of TMI. How could so many people be bamboozled?


It's not just Fyre Festival that has Americans glued to updates and aftermath. Much like the true crime craze that spawned Making a Murderer, Serial, and Dirty John, true scam stories have grown into their own popular genre. In the last year alone, the story of author Lee Israel's elaborate bait-and-switch scheme was made into the Oscar-nominated film Can You Ever Forgive Me?; Elizabeth Holmes' alleged lies about her medical company, Theranos, became an ABC podcast, an HBO documentary, a forthcoming feature film starring Jennifer Lawrence (via People), and a Hulu series with Kate McKinnon; and Shonda Rhimes is turning the story of the "Soho Grifter," Anna Delvey, who was just found guilty of conning "friends, banks and even an executive in charge of a private jet company out of over $250,000 in cash, goods, and services," according to Time, into a new Netflix series. Producers and studio execs aren't just spinning these true stories into consumable pop culture without a willing audience, though. It's our insatiable curiosity about who scams, who gets scammed, and why that keeps us invested and the adaptations coming.

Lo, 24, says she's always been a fan of scam stories, but started following them more closely when, in 2017, Zoella, a British beauty YouTube personality, pedaled a luxury "12 Days of Christmas Advent Calendar" that was promised to contain enviable home and lifestyle products, but turned out to be full of cheap items that weren't worth the $66 price tag.

"I just couldn't believe the audacity of it," Lo says, adding that she started looking further into YouTube and internet personalities like Caroline Calloway who, Business Insider reports, held "'creativity workshops' for her followers that were criticized as poorly run and derided as 'scams.'" The events were compared to (what else?) the Fyre Festival.

There’s something captivating about the ways scammers lure people in; the combination of entitlement and denial stands out to me.

"The Caroline Calloway 'scam' kept me hooked for ages," Lo continues. "Probably because I couldn't, and still can't, work out if she is a scammer mastermind of just an incredibly self-aggrandizing privileged white girl who doesn't realize how much she's ripping people off."

Lindsey, 30, says she's been enthralled by stories about women like Holmes and Delvey, but also by Keith Raniere, whose NXIVM cult, alleged to have involved blackmail and sexual abuse, will be the focus of of a docuseries this year.

"There’s something captivating about the ways scammers lure people in; the combination of entitlement and denial stands out to me," she tells Bustle. "I’m invested because I want to see how long people can balance these contradictory outlooks before being caught."

Justin Sullivan/Getty Images News/Getty Images

On the expert side, clinical psychologist and host of The Kurre and Klapow Show, Dr. Joshua Klapow, says we are drawn to scams for some of the same reasons we are drawn to looking at an accident when we pass it on the highway.

"We are vicarious learners," Dr. Klapow tells Bustle over email. "We learn not just by experiencing things directly but also by watching others experience."

Scams represent a kind of danger, he explains. "Maybe not life threatening, but a danger. By watching these stories we are coming closer to the very thing that could harm us. It’s almost a hardwired way of learning. We are drawn to them because they allow us to see what might happen to us without having to actually endure the pain of being put through a scam."

Scam story fan Ashley Louise, 31, agrees. She says she thinks there's an interest in the likes of Holmes and Fyre Fest creator Billy McFarland because they were self-styled entrepreneurs whose actions were allegedly putting people in danger.

"I think a lot of their behaviors — fake it to you make it, embellish (lie!), close the deal, figure out how to get it done later — are all pretty typical behaviors for a segment of [venture capitalist] folks raising money and trying to aggressively grow their businesses."

"These two are the most interesting to me because they just seem to operate in a totally different reality," 27-year-old Kate says of Holmes and McFarland. "They fundamentally didn't seem to understand that what they had done was wrong until they were punished for it. You can even see shades of it with these college admissions scam parents. When you have that kind of money, blind confidence, and whiteness, illegality feels relative. And it also makes people much more likely to believe you. I think that's a pretty scary thing and it's the root of so many issues in this country. It feels like a social responsibility almost to figure out how these people got as far as they did."

... If you trick a bunch of rich people, that's OK — they had it coming.

"I think the negative is it gives a very poor message, which is to say that we're rewarding bad behavior," says Dr. Pamela Rutledge, Director of the Media Psychology Research Center, of our hunger for scam stories. She says the reason we as viewers are so interested in the way that these cons play out is that scammers are also storytellers.

"All of those [movies] where the villain is now the hero and is someone who is charismatic, they had to have a really good story to pull the thing off," she says, speaking over the phone. "In the narrative, whoever was cheated had it coming, or has money to spare or something, so if you trick a bunch of rich people, that's OK — they had it coming. If you cheat a bunch of venture capitalists, that's OK — we're currently not very high on venture capitalism. And we're also interested in — just like you're interested in the best singer, best dancer, the best something, these are people who pulled off something sort of extraordinary. How did they do that?"

Dr. Klapow says that part of the appeal is the need to figure out how and why others were fooled so we can keep ourselves from falling prey to the same kinds of scenarios.

"Humans need certainty and rules in their world in order for them to feel most at peace," he says. "Scam artist stories are stories that say the world is not certain, it is not rule-following and that bad things can happen to us. When a scam artist story ends with the scammer being caught, we are validated and frankly comforted that our world is right, and orderly."

Dr. Rutledge says audiences are as innately curious about how scammers can be successful as they are about why those who were scammed fall for them in the first place. "You want to reassure yourself that it couldn't happen to you," she says. "Your fascination has to do with, at some level, the relevance to yourself and your basic survival instinct — what does this have to do with me and would I be vulnerable for this? So you're very interested in these outliers because you need to determine your own risk level. And of course everyone thinks they couldn't possibly be conned."

The fascination, then, is not only with the people who fell for the frauds, but with the frauds themselves, we either consciously or subconsciously attempt to avoid our own pitfalls in the future. But Kaplow sees a dehumanizing downside to the trend.

"The only negative really is the degree to which we relish in seeing others harmed. If that is the primary draw then it feeds an unhealthy apathy about the world and other humans," he says.

"It helps to calm [our] anxiety by dissecting these people or even fetishizing them because it seems to create a sense of control, or the ability to say 'I would never behave X way in this situation, so I'll be safe' or 'I would never fall for that, I'm too smart for that,'" Kate posits. "Which of course is totally bogus."

Of course, there's also the entertainment aspect. When true scam stories are turned into content, those behind the camera and in the editing room are looking to tell a compelling story. Thanks to the TV version of a viral documentary feature hit, MTV viewers can watch one play out weekly.


"The movie Catfish really opened up a love of scam stories for me because it framed this elaborate scam as a thriller, which is really kind of the format they've all adopted now, even though ultimately it kind of just has a sad ending," says 29-year-old Marie.

The appeal of fictional scammer stories like The Hustle and Ocean's 8, meanwhile, also incorporate the fact that, in the past, on-screen depictions of scam artists have often been relegated to the men: Catch Me If You Can's Frank Abagnale, Jr., for one, and Bernie Maddoff, who had a mini-series, an HBO movie, and a documentary dedicated to his Ponzi scheme. It's only been in the last year or so that women scammers have gotten more play, from Melissa McCarthy's depiction of Israel in Can You Ever Forgive Me? to the continued prevalence of Holmes in media and popular culture.

Ashley says she's looking forward to Hollywood's versions of the Holmes and Delvey scandals, partly because she thinks they'll be, well, entertaining.

"One thing that has so far frustrated me with the Theranos coverage is that it's felt very focused on the science and very cut and dry business stuff, and what I'm really here for the saucy bits," she says. "There must have been tons of crazy stuff going on — apparently she's obsessed with costume parties — and that's more of the details I want."

Kate, meanwhile, is fascinated by how quickly Hollywood jumps on these stories these days.

Holmes, McFarland, and Delvey are getting their comeuppance legally, to be sure, but culturally? Mixed messages at best.

"There's something to be said for the way we almost immediately allow these figures to enter the cultural imagination. Anna Delvey has made requests from prison that Jennifer Lawrence or Margot Robbie portray her. She has a courtroom stylist. This girl knows her star is still on the rise even behind bars," Kate says. "Here we are in 2019 with a new JT Leroy film! And it's only a matter of time before we get probably Jake Gyllenhaal in the Dan Mallory biopic. Holmes, McFarland, and Delvey are getting their comeuppance legally, to be sure, but culturally? Mixed messages at best."

These mixed messages, Dr. Rutledge says, are being spread because when we're investing time, energy and money into stories and entertainment about these crimes, we're raising the con artists profiles and potentially providing them profit.

"When you see Shonda Rimes buying the story of a woman who cheated out banks and all that stuff, you have to say 'Is it appropriate for people to benefit when they've caused damage? Is it morally ethical or morally appropriate to promote a story without also showing the consequences?'" she asks.

Kate explains that she also sees a connection between the interest in true crime and true cons, one that isn't always so positive.

"I keep thinking about all these upcoming projects and our excitement for them compared to the response to the upcoming Ted Bundy film. Obviously, Bundy's crimes are on an entirely different level of psychopathy and tragedy and I agree should not be made salacious, but scams are not victimless crimes. A man killed himself as a [Editor's note: alleged] result of Elizabeth Holmes' bullying and liesand others made life-altering medical decisions. Families lost life savings because of Bernie Madoff. Madoff himself lost his son to suicide," she says. "So I think the question going forward is where do we draw the lines when giving these people notoriety, and what does that notoriety look like, since that's the thing all of them, serial killer or serial scammer, are after in some way or another."

With all the controversy, there are some positive things we can learn from giving so much time and energy to learning about scams and those who pull them. Dr. Klapow offers that these stories can teach us not to be cynical, but to be more engaged and aware.

"We can learn that the world can be unpredictable, that we need to be aware and not overly naive, that bad things can happen to good people, and that we can trust, but not trust blindly," Dr. Klapow says. "These are all protective lessons that help keep us safe in our world. Also to the extent that the scam artists get caught — our unconscious desire to have justice in the world is fulfilled."

Investing in fictional scams is fairly safe. Still, Dr. Rutledge suggests we consider the ramifications of giving our attention and energy to certain con artists, and consider who's inevitably benefitting from that attention and energy.

"We should not be so in love with the story of how it happened," she says, "that we forget about the real world outcome."