“Ripley” explores the eternal appeal of the con man - The Washington Post
Democracy Dies in Darkness

Scammers are having a cultural moment. Why are we so obsessed with them?

Steven Zaillian’s “Ripley” and Emerald Fennell’s “Saltburn” explore the appeal — and the depravity — of con men

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Matt Damon in Anthony Minghella’s “The Talented Mr. Ripley.” (Shutterstock)
8 min

“New Anna Delvey just dropped.”

That’s what a friend posted in a Slack channel recently upon reading about a New York City promoter associated with an archipelago of buzzy restaurants and bars, who had been sued for allegedly pocketing the money of people who thought they were his investors.

It was a particularly good example of the specific kind of excitement that spreads through chats and DMs when it appears there’s a new con artist on the horizon. From the aforementioned Delvey, a.k.a. Anna Sorokin, the fake heiress shacking up at the finest hotels, to disgraced congressman George Santos, spending campaign funds on Botox, there’s something delectable about consuming the details of a grift — especially when there’s an aura of glamour around it.

You could say that scammers have been having a pop cultural moment of late. From the disastrous Fyre Festival impresario Billy McFarland to Theranos founder Elizabeth Holmes and her faulty medical devices to crypto bro fraudster Sam Bankman-Fried, it feels like we’ve been inundated with these stories. But the con artist has long had a hold on the popular imagination. How else to explain the arrival of another iteration of everyone’s favorite fictional con man, Tom Ripley?

Steven Zaillian’s “Ripley,” the latest adaptation of Patricia Highsmith’s 1955 novel “The Talented Mr. Ripley,” was released on Netflix last week. This one stars Irish actor Andrew Scott as the title character, who is recruited by the wealthy father of Dickie Greenleaf (Johnny Flynn) to bring his dilettante son home from Italy. Given that the story is over a half-century old, it is no spoiler to say that Tom takes the elder Greenleaf’s money and eventually ends up murdering Dickie and assuming his identity in Rome.

This, of course, is far from the first time Ripley has been depicted in pop culture. Perhaps most famously, Matt Damon played the character as a youthful beauty in Anthony Minghella’s 1999 film “The Talented Mr. Ripley.” Before that, the French heartthrob Alain Delon took on the role in 1960’s “Purple Noon.” Elsewhere, John Malkovich, who makes an appearance in the Netflix show, was Ripley in the 2002 “Ripley’s Game,” a take on one of Highsmith’s later Ripley novels. Tom has also been portrayed over the years by Dennis Hopper and Barry Pepper.

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So why do we keep adapting this mid-century novel? Zaillian said it goes back to Highsmith’s text, which she wrote from Tom’s point of view. “He has these traits that I think we all relate to,” the director said in a phone interview. “He has aspirations, envy, pride, desires, the same things that we all have and that we try to keep in check. He’s not able to keep them in check, and that’s where the story leads.”

Zaillian’s assessment gets at the enduring appeal of the con man, and why it’s so easy to get a little thrill when a “new Anna Delvey drops.” These characters, be they real or fictional, are relatable. Almost.

For the comedian Laci Mosley, whose “Scam Goddess” podcast, in which she digs into scams new and old, is the subject of an upcoming book, the cultural attraction to scammers is twofold. “I think that people are curious about people who have the audacity to create rules of their own and exist in a reality that is essentially something that they have dreamed up for themselves and works for them,” she said.

But also, she added, people are fearful of being scammed — which contributes to the fascination. That explains the recent virality of a New York magazine story in which a writer admitted to falling for a scam call. Other recent films have tapped into the nightmare of being at the opposite end of a grifter: In the Jason Statham thriller “The Beekeeper,” the hero goes on a rampage after his landlady falls for a phishing scheme. Meanwhile, in the upcoming comedy “Thelma,” June Squibb becomes an elderly action hero after she falls for a phone scam.

In a 1988 profile of Highsmith in the New York Times Magazine, journalist Joan Dupont tried to identify the appeal of the Ripley novels. “The mystery is in the protagonist’s mind, his makeup,” Dupont wrote. “We sympathize with him and hope he will not be found out. Often, he isn’t. Life may even get better for him, as it does for the gentleman forger and occasional murderer Tom Ripley, the protagonist of four novels, who lives the life of a country squire on his estate near Fontainebleau.”

In real life, there seem to be two tiers of grifters. Some are essentially amusing. Delvey, for instance, has been embraced by the same New York society set she tried to con her way into. In September, she co-hosted a fashion show for the designer Shao Yang at the East Village apartment building where she is under house arrest. (She was aided by celebrity publicist Kelly Cutrone.) Those she defrauded are still angry. Her former friend Rachel DeLoache Williams, who lost $62,000 to Delvey’s schemes, is trying to sue Netflix over her portrayal in the series “Inventing Anna,” arguing that the show presents “Sorokin’s brazen willingness to lie, cheat and steal her way past supposedly unjust obstacles rooted in bureaucracy, ageism and sexism as admirable.” Others now see Delvey as a folk hero with a chic ankle bracelet.

Then there are the scammers the public abhors. Theranos founder Elizabeth Holmes, for example, was met with scorn when she attempted to reinvent herself as “Liz” in the New York Times, ditching her famously deep voice and framing herself as a maternal figure, before starting her prison sentence. That’s because her grift was cruel rather than merely materialistic. Her official crime was fraud, but she also toyed with people’s lives.

Naturally, both Holmes and Delvey have already been the subject of TV shows, too.

Of course, fiction gives audiences permission to root for con men even when the crimes are serious. Take, for instance, Emerald Fennell’s Ripley-infused movie “Saltburn,” which became a viral sensation last year. The film ends with its middle-class-striver protagonist Oliver (Barry Keoghan) having systematically dispatched the rich Catton family and taken over their family estate. When he dances, naked, through the halls, his triumph is cathartic even if Fennell doesn’t exactly celebrate him. There’s a reason the song in those final beats, Sophie Ellis-Bextor’s “Murder on the Dancefloor,” has had such a revival. It’s fun to emulate Keoghan’s movements — there’s dastardly wish-fulfillment afoot.

Tom Ripley is also a murderer, a fact that the new series doesn’t gloss over. (The scenes of him trying to dispose of corpses are extended and brutal. Turns out it’s hard to cover up a killing.) But Zaillian said he doesn’t see Ripley as a psychopath. “I thought he was, in many ways, a normal person who goes too far with the things he wants or the things he needs,” the director said.

We’re taught to think of con artists as abnormal — after all, they operate outside the boundaries of socially acceptable behavior. But it’s the normalcy of their desires that draws us back to them again and again. Scott’s Ripley demonstrates this perfectly. He’s older and a little more faded than Damon or Delon were when they played the character, less defined by the glint in his eye than the exhaustion we all feel. His wants are simple: He wants a beautiful home. He wants art. He wants friendship.

“I think Ripley represents the con artist in the most interesting, complex, purest form,” said documentarian Yon Motskin, creator of HBO Max’s scammer series “Generation Hustle.” “It has nothing to do with money. It’s about identity and class.” Ripley, yes, covets some of the things Dickie has, but it’s less about possession of those things than it is about rising above his lot in life, which is otherwise dreary.

“It’s the bastardization of the American Dream,” Motskin added. “Like, ‘Well, I can’t get there myself so I’m going to go and pretend to be somebody and probably then eventually commit crimes and maybe even kill somebody to get there.’”

The scammer — real or invented — puts the audience in a moral quandary. Can we identify with them even as we root for their downfall? Apparently: The dream is to spend just a moment living with their lack of shame. “For me, scamming is all about having people have fun before the fall,” Mosley said.

So when a new Delvey drops or a new Ripley adaptation premieres, we tune in.