10 TV Shows and Films Featuring the Juiciest Schemes and Swindles You Absolutely Have to Watch

FYRE: The Greatest Party That Never Happened

On paper, the FYRE Festival was every partygoer’s dream. Imagine a two-weekend Bahamas getaway with the promise of luxury accommodations, fine dining, and a musical lineup consisting of top artists.

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FYRE: The Greatest Party That Never Happened

Billy McFarland and Ja Rule’s brainchild made headlines in 2016, bolstered by elaborate marketing collateral featuring high profile personalities such as Kendall Jenner, Bella Hadid, and Hailey Bieber. With ticket costs purportedly ranging from $4,000 to a whopping $250,000, the festivities certainly did not come cheap—but it was a small price to pay for the wealthy, who landed to find disaster relief tents instead of swanky cabanas, a slice of cheese on toast instead of steak and caviar, and no options for return flights. Yikes.

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FYRE: The Greatest Party That Never Happened

Netflix’s FYRE: The Greatest Party That Never Happened unpacks this incredible disaster and clues us in on what really happened. The Guardian describes it as something that “feels like scrolling through Instagram or Twitter,” and it is right on the money. We get clips of would-be attendees looting the tents, of festival producer Andy King turning into an internet sensation thanks to that comment about Evian bottled water, and of the saddest-looking cheese sandwich in the world. It sheds light on more serious matters, too, including the Bahamians whose services were tapped for the festival, only to end up in thousands of dollars in debt. There’s certainly satisfaction in seeing McFarland pay for his crimes. If only the same could be said for Ja Rule, who, apart from several lawsuits, seems to have gotten off scot-free.

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Inventing Anna

To no one’s surprise, some scams are all about the money, such as in the case of Anna Delvey—or rather, Anna Sorokin. The so-called socialite/heiress would spend $4,500 on personal coaching sessions and tip the staff at the 11 Howard $100 in cold hard cash. She shopped like there was no tomorrow, attended all the hottest parties, knew all the best people, and refused to let her friends pay for lunch.

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Inventing Anna

With so much money on her, how could anyone ever suspect her of being a fraud? But when the credit cards started getting declined and when those she borrowed money from—a rather odd habit for someone so exorbitantly wealthy—were getting paid via anonymous Venmo accounts, the people in her orbit began to realize that something was afoot.

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Inventing Anna

Julia Garner steps into the shoes of the titular con artist in Shonda Rhimes’ Inventing Anna, a nine-episode miniseries released on Netflix just this year. Despite its salaciously intriguing source material, the show doesn’t quite know which tone it wants to go with. Reviews from critics have been mixed, but the cast’s spectacular performance makes it an entertaining watch. Emmy Award winner Garner plays Sorokin to sketchy perfection and Laverne Cox is a delight as life coach Kacy Dukes. Ben Rapaport’s cameo as—surprise, surprise—FYRE Festival scammer Billy McFarland, who was, for a time, Sorokin’s roommate. Birds of a feather do flock together.

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The Tinder Swindler

Simon says: “Send money now! My enemies are after me.” And Cecilie Fjellhøy, Pernilla Sjöholm, and Ayleen Charlotte hasten to obey. He’s the love of their life. He’s a dear friend. Of course they would go out of their way to help him, even at their very own financial and emotional expense. And this is how the Tinder Swindler—who calls himself Simon Leviev under the pretense of being the heir to the Israeli diamond tycoon family—crafted and spun this elaborate game of hearts.

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The Tinder Swindler

He would match with women on dating app Tinder, con them into long-distance relationships, fake being in danger via the use of photos and videos of his injured so-called bodyguard, and ask them for their credit card details. Why? Because his “enemies” are after him and he can’t be tracked.

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The Tinder Swindler

We all found ourselves glued to our screens when The Tinder Swindler came out on Netflix, jaws practically on the floor as we watched Leviev Ponzi scheme his way from Cecilie to Pernilla to Ayleen, using the money from one woman to take another on a ridiculously expensive romantic getaway or party.

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The Tinder Swindler

The documentary film was met with high acclaim, with critics describing it as addictive, solid, and even heartbreaking—a must-watch for every true crime aficionado. At a runtime of 114 minutes, this is a gripping retelling of the most dangerous game of Simon Says yet. So next time you go on Tinder, be careful of who you Swipe Right on.

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WeCrashed

Not a fan of spending your 9-to-5s ensconced in a boring, claustrophobia-inducing cubicle? Disgraced WeWork co-founder Adam Neumann wasn’t, either. Wanting to change the way offices were set up, he and his business partner Miguel McKelvey began renting spaces out to entrepreneurs, freelancers, and other businesses on a monthly or yearly contractual basis. Investors such as JP Morgan Chase & Co., SoftBank, and Goldman Sachs came calling, landing Neumann in the billionaires club. Everything got to his head; Neumann began to lead an extremely lavish lifestyle, purchasing a $60 million dollar plane, among other things, amidst rapidly growing suspicion and discontentment from employees.

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WeCrashed

Apple TV’s WeCrashed explores and dramatizes how this remarkable success story ended up in shambles. After WeWork filed for an IPO in 2019, account after account of Neumann’s unscrupulous ways of conducting business came pouring out, revealing just how much money WeWork was losing. His expansion plans were simply unsustainable, forcing him to keep operations afloat by scamming money from his investors.

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WeCrashed

Jared Leto and Anne Hathaway play Neumann and his New Age advocate wife Rebekah, respectively, chew the scenery with their trademark theatrical aplomb—perfect for portraying a couple that elevates each other’s reckless behaviour. This is just one of many WeWork stories, but the Leto-Hathaway partnership gives the show a bit of a love story treatment; whether this is a come-on or a detriment all depends on you.

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The Dropout

It should go without saying that Theranos founder Elizabeth Holmes has got to be one of the greatest fraudsters of all time. Only 19 when she founded her multibillion biotech start-up, this perpetually turtleneck-clad—she deeply idolized Steve Jobs—entrepreneur managed to dupe the American medical community into thinking the Edison, her so-called revolutionary device, could successfully run multiple tests using only a single drop of blood. This, of course, was just as fake as the odd, throaty baritone speaking voice Holmes adapted in order to assert more power. Simple, yes, but a chilling first step in the establishment of what would be a long con that was finally unraveled in 2015 after John Carreyou’s tell-all was published in The Wall Street Journal.

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The Dropout

Amanda Seyfried delivers a powerful performance as the Theranos founder. Her Holmes is likable; she is smart, she is ambitious, she is awkward, she is kind. The viewer—women, especially—can’t help but root for her. She’s propelling herself forward in a male-dominated industry, never giving up despite the setbacks. And, more importantly, she wants to help make the world a better place.

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The Dropout

It just sucks she felt the need to lie to sell the Edison narrative, and that she kept on exercising her privileged position to keep doing so. The Dropout doesn’t seek to excuse her or absolve her, and she does get what she deserves. The real Miss Holmes is currently awaiting sentencing.

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Dirty Money

Here’s an understatement: the world is filled to the brim with all sorts of problems. And if we were to craft a documentary highlighting even just the major ones… Well, we’d have too much material and too little time on our hands. Corporate greed and securities fraud are common evils in the realm of capitalism, especially when the super rich come into play. Such instances happen time and time again, simply because the system that is currently in place lets these guys get away with their crooked dealings, and little has been done to make sure no repeat performance ever takes place.

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Dirty Money

Dirty Money is a two-season documentary series highlighting various incidences of financial fraud, with each episode helmed by a different director. These are serious, hard-hitting exposes, all of them gripping, informative, and offering the audience plenty to digest. The first season opens with Emissionsgate, also known as the Volkswagen emissions scandal, and closes with a look at how Donald Trump’s unscrupulous business practices and deceiving marketing tactics.

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Dirty Money

Season two is just as strong, with the Slumlord Millionaire episode being the highlight of the bunch. Focusing on Trump son-in-law Jared Kushner, it explores his sketchy background and dissects how he may have used his prestigious position to secure deals for his private businesses. On another note, the Guardians, Inc. episode was pulled from streaming after Netflix was faced with a defamation lawsuit.

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Operation Varsity Blues: The College Admissions Scandal

In 2019, federal prosecutors made public their findings on a felony conspiracy that would rock the boat with regards to the American college education admission process. William Rick Singer, the CEO of Key Worldwide Foundation and The Edge College & Career Network, pleaded guilty to fraudulently facilitating college admissions decisions in several top universities for over 750 families. To go about his dirty work, he utilized two methods: helping the applicants cheat on the entrance exams and falsifying credentials in athletic excellence.

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Operation Varsity Blues: The College Admissions Scandal

A total of 50 people have been implicated, including parents of the applicants and several coaches and administrators. A few famous names have popped up among those charged, including actresses Lori Loughlin and Felicity Huffman.

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Operation Varsity Blues: The College Admissions Scandal

FYRE director Chris Smith adapts a different tone for Operation Varsity Blues: The College Admissions Scandal. This is likely the most straight-to-the-point documentary film he’s ever done, taking the transcripts of wiretapped conversation and having actors portray all those involved. Matthew Modine takes an excellent turn as the shamelessly clever Singer, with critics holding his performance to high regard. Yet what is most valuable about this film is how it frames the very concept of admission itself: that the prestige of having entered an elite educational institute can be bought for as long as you can afford it. Again, it highlights a massive flaw in the system. In an ideal world, no one should be allowed to do such things—and criminals like Singer should not be allowed to walk free.

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The Woman Who Wasn’t There

To craft a false narrative about having survived one of the most heinous terrorist attacks in history is simply terrible. Spanish citizen Alice Esteve Head created an online support group for 9/11 survivors under the name Tania Head. She claimed to be an employee at Merrill Lynch, and that she had been inside the South Tower when United Airlines Flight 175 hit.

The Woman Who Wasn’t There

Head’s detailed accounts propelled her into the limelight, often being invited to speak to the media and at conferences, and even conduct tours in the WTC Visitor Center. It was only in 2007 that her lies began to unravel. The New York Times wanted to publish her account as part of an anniversary piece, but could not find any record of her employment at Merrill Lynch. La Vanguardia reported that she had actually been in class in Barcelona during the World Trade Center attacks. This revelation caused Head to back out of any and all interviews, and leave New York.

The Woman Who Wasn’t There

Angelo J Guglielmo, Jr., a member of the WTC Survivors’ Network and an ex-friend of Head’s, co-write a book called The Woman Who Wasn’t There, and directed a documentary that shares the same title. It features accounts from her former friends, showing how admiration turned into fury when they eventually realized that some details from Head’s stories didn’t seem to add up. Aside from being exposed, this fraudster—who may have masterminded another lie claiming she had died by suicide—gets her comeuppance. As a result of her horrible, elaborate lie, Head was fired from her position at an insurance company.

The Puppet Master: Hunting the Ultimate Conman

Coercive control is defined as the use of intimidation and humiliation or other forms of verbal abuse to frighten a person, establishing dependency by monitoring their behavior and isolating them from other support systems. Conman Robert Hendy-Freegard was particularly masterful in this area. He masqueraded as an MI5 agent for over a decade, pressuring his victims to bend to his will through various threats, allowing him access to their finances and their lives.

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The Puppet Master: Hunting the Ultimate Conman

In 1992, he befriended three students from Harper Adams University, going as far as having them sever ties with their families and “go undercover” with him based on false claims of being in danger. In 2011, he met divorcee Sandra Clifton through an online dating site, and seduced and coerced her to the point that she left her own children to go off the grid with him.

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The Puppet Master: Hunting the Ultimate Conman

The Puppet Master: Hunting the Ultimate Conman devotes itself to exploring how Hendy-Freegard utilized the same or similar coercive control methods to handle his targets for almost a decade—an intriguing and terrifying feat. It’s a compelling story without a definite ending told in a straightforward manner. Hendy-Freegard was released after only a couple of years in prison; he is still believed to be with Sandra Clifton to this day and their exact whereabouts remain unknown.

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The Act

The Dee Dee Blanchard murder may as well be part of the neophyte true crime aficionado’s primer. In 2015, the authorities found her lying in a pool of blood, having passed from multiple days old stab wounds. Her daughter Gypsy Rose, who suffered from leukemia, muscular dystrophy, and other complications caused by premature birth, was curiously missing. Police tracked her down, and discovered that she had none of the health issues her mother claimed she suffered from.

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The Act

This was all an act orchestrated by Dee Dee, who had coerced her daughter to pretend to be ill in order to gain sympathy from others. This led Gypsy Rose and her boyfriend Nicholas Godejohn to murder her mother. The two attempted to flee, but were caught after appearing on security cameras at several stores. She was sentenced to ten years with parole eligibility in 2024; he was sentenced to life without parole.

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The Act

Hulu’s The Act is a limited series starring Joey King as Gypsy Rose and Patricia Arquette as Dee Dee. It shows how the mother-daughter relationship begins to fray at the seams, with Gypsy Rose wanting to gain a certain degree of independence. It takes a turn for the worse when she finds out the truth, leading her to orchestrate the murder. The story feels a little too stretched out over eight episodes; the series could very well benefit from a shorter run time, paving the way for tighter storytelling. This doesn’t take away from the fantastic work King and Arquette put into their roles, which is what makes the show worth watching.

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