A spectacularly dazzling corner of true crime has been snatched by scammers. Con artists who have the gift of gab, terrific charisma, or a sales pitch too good to be true, can be as fascinating as they are infuriating. If you can’t get enough of tales of scams, cons, and deceptions, we’ve got you covered with a collection of daring documentaries.
Whether you want the rundown on infamous scam artists like Elizabeth Holmes, or the story behind the absolute mess that was Fyre Fest, or the outrageous truth behind a submarine scheme, a faked fast food giveaway, or a menacing imposter, there’s a documentary for you. Some of them are as shocking as they are amusing, others are riveting and unnerving. All of them are worth the watch, even as they give you goosebumps.
Here are the best documentaries about scammers, now streaming.
1. The Inventor: Out for Blood in Silicon Valley
Enter the absolutely unreal delusion of disgraced Theranos founder Elizabeth Holmes in The Inventor: Out for Blood in Silicon Valley. Academy Award winner Alex Gibney walks viewers through the scam concocted by the ex-CEO, which not only garnered the support of numerous high-profile investors but even saw its entirely fake technology — a blood-testing device called « Edison » — begin a pseudo rollout in actual pharmacies.
Repurposing some incredible footage of Holmes — intended for use in a Theranos advertising campaign — Gibney renders a stunning portrait of a now convicted fraud. The result is a mesmerizing watch that will make you question how easy you’d be to fool when faced with one of the most notorious liars of the 21st century.* — Alison Foreman, Entertainment Reporter
How to watch: The Inventor: Out for Blood in Silicon Valley is now streaming on HBO Max.
2. The Lady and the Dale
HBO has a library of sensational true crime offerings, yet this 2021 mini-series is uniquely fascinating. Directors Nick Cammilleri and Zackary Drucker unfurl the times and trials of Elizabeth Carmichael, who was not only a nationally recognized automobile executive and infamous con artist, but also a wife, mother, and transgender trailblazer.
For decades, her story has been framed by those who despise her, resulting in a narrative rife with speculation and transphobia. In this challenging and boldly funny four-episode documentary mini-series, Carmichael’s story is reclaimed by balancing the perspective of her haters with in-depth interviews with those who knew her best. With animated photography, a playful soundtrack, and a cheeky sense of adventure, The Lady and The Dale aims not only to showcase the complexity of the late Carmichael but also to capture her spirit. All this makes for a watch that is surprising, thrilling, and unforgettable.* —Kristy Puchko, Film Editor
How to watch: The Lady and the Dale is streaming on HBO Max.
3. The Tinder Swindler
Beyond its impossibly fun name (say it three times fast), 2022’s The Tinder Swindler is an engaging look at a scam that unfolded in the hallowed halls of Tinder. The titular swindler is named Shimon Hayut, but on Tinder, he presented himself as Simon Leviev, an incredibly wealthy man who whisked matches away on lavish journeys and heaped them with gifts. However, he would then trick these women into lending him large sums of money — only to never pay them back.
As the film plays out, Hayut’s victims team up to take him down. Will this serial scammer face justice, or get away scot-free? Don’t google the answer, dive in. — Belen Edwards, Entertainment Reporter
How to watch: The Tindler Swindler is now streaming on Netflix.
4. The Imposter
Bart Layton’s 2012 documentary is maybe the most mind-bending offering on this list, arguably inspiring not one but two twisted horror movies: Orphan: First Kill and Titane.
The story begins with a Texas family, who has spent years hoping for the return of their teen son who vanished without a trace in 1994. When a phone call from Spain announces their boy has been found, the Barclay clan is initially elated. But there’s something about this recovered kid, something about his ears, the eyes, and the way the Texan now speaks in a French accent. It’s not a big reveal that this imposter is the infamous con artist Frédéric Bourdin. But as Layton interviews the Barclays and Bourdin in increasingly tense interviews, every other turn of this story is ruthlessly riveting. But be warned: This scam story doesn’t pay off with a happy ending. —K.P.
How to watch: The Imposter is now streaming on Peacock.
5. McMillions
For more than a decade starting in 1989, a veritable army of crooks and stooges bilked McDonald’s out of $24 million worth of winnings from its annual McDonald’s Monopoly sweepstakes. It was such a sprawling scheme that in 2020, HBO turned it into a documentary miniseries directed by James Lee Hernandez and Brian Lazarte. Across six episodes, the fascinating and frequently hilarious doc introduces us to colorful characters on both sides of the law as it digs into the particulars of the criminal enterprise and how it eventually fell apart.
By the time it’s all over, you’ll know the who, what, when, where, why, and how of the historic McDonald’s Monopoly fraud case. But you’ll also be left with plenty of questions about what McMillions‘ most memorable character, FBI Agent Doug Matthews, isn’t telling us.* — Adam Rosenberg, Senior Entertainment Reporter
How to watch: McMillions is now streaming on HBO Max.
6. Operation Varsity Blues
Remember the 2019 college admissions scandal that featured TV stars like Lori Loughlin and Felicity Huffman? Netflix’s documentary about the scam — led by mastermind Rick Singer— invites you to think about that formative college application period and never lets you lose sight of it. Imagine how teens who worked tirelessly to get into college on their own merits felt upon learning that select students were illegally admitted to the nation’s most highly regarded universities — simply because their wealthy parents cheated the educational system.
If you turn on Operation Varsity Blues hoping to learn more about high-profile parents involved in the scandal, like Loughlin, or her YouTube-famous daughter, Olivia Jade, you will. But the overarching narratives of inequality, the volatility of hyping up « elite » institutions, and the exposure of a shattered system that sets the white and wealthy up for innate success, are the things that will linger long after the end credits roll.* —Nicole Gallucci, Senior Editor
How to watch: Operation Varsity Blues is now streaming on Netflix.
7. Fyre: The Greatest Party That Never Happened
It was the cheese sandwich seen ’round the world, and the beginning of the end of aspiring impresario Billy McFarland’s biggest scheme.
If you believed the sponsored content posted by celebs on Instagram, the first Fyre Festival was poised to be a party paradise, full of kick-ass music, haute cuisine, and bikini-clad models frolicking on gorgeous beaches. Then guests, who shelled out big bucks for an island oasis vacation, arrived to find rusty buses and urine-soaked tents. The backlash and schadenfreude came fast and hilarious. Director Chris Smith takes audiences behind the scenes of this fraud-filled festival, speaking not only to the stiffed guests but also to the former McFarland employees, who smelled smoke but couldn’t stop the Fyre.* —K.P.
How to watch: Fyre: The Greatest Party That Never Happened is now streaming on Netflix.
8. Bad Vegan: Fame. Fraud. Fugitives.
If you think Bad Vegan is a docuseries focused on exposing something wild about veganism, you’ve been scammed. It is, however, the four-part tale of restaurateur Sarma Melngailis, owner of New York vegan restaurant and celebrity hotspot Pure Food and Wine, and the con man she married and lost her fortune to: Shane Fox (real name, Anthony Strangis).
Fyre: The Greatest Party that Never Happened director Chris Smith, who also exec-produced Tiger King, delves into the events that led to Melngailis being known as the ‘Vegan Fugitive’. Through interviews with perplexed former staff, lawyers, and Melngailis herself, the series examines how Strangis encouraged her to drain over $1.6 million of the restaurant’s funds, and how the pair ended up giving the game away by a now-infamous Domino’s pizza order. And if you didn’t realize the documentary would explore the potential immortality of a pitbull, again, you’ve been duped. —Shannon Connellan, UK Editor
How to stream: Bad Vegan is now streaming on Netflix.
9. Operation Odessa
Seeking a true-crime tale that’s stranger than fiction? Then you’ll love every moment of this deranged yet oddly delightful doc.
Operation Odessa kicks off with a Russian mobster known as Tarzan and climaxes with a shady deal to sell a Soviet submarine to a Colombian drug cartel to ship cocaine to the U.S. The story on its own is wild enough to make Tiller Russell’s true-crime trip worth the watch. However, the true treasure here is Tarzan and his cohorts, who offer interviews that are not only astoundingly frank about their criminal endeavors but also full of panache. Whether they’re detailing arson hits, racy strip club acts, or how they conned a bunch of Soviets by pretending to be Pablo Escobar, they do so with a mischievous grin, a flair for storytelling, and a sailor’s tongue that’ll leave you drop-jawed and howling with laughter.* —K.P.
How to watch: Operation Odessa is available for purchase on iTunes.
10. My Old School
One of the most curious documentaries of 2022 begins with the day in 1993 when a new student turned up at a Scottish secondary school calling himself Brandon Lee. From the start, there was something about hm that seemed different. But his classmates embraced him as one of their own. That is until the scandal broke.
Director Jono McLeod was one of Lee’s class mates, and uses these bonds to urge his peers — as well as the infamous Lee himself — to share their recollections about these wild school days. Interviewing them in a classroom setting, often in pairs, adds a convivial atmosphere that keeps things fun, even as the revelations begin veering into the bizarre. But more spectacle comes in the form of flashbacks rendered in Daria-inspired animation, with actor Alan Cumming lending his voice as Lee. The result is a documentary that deals deftly with the wonder of nostalgia and the dangers of getting stuck in the past. —K.P.
How to watch: My Old School is available for purchase on Apple.
11. Catfish
It’s the eye-popping documentary that birthed a new definition in true crime — as well as a spinoff series. In the early days of social media and online dating, 20-something Nev Schulman had made a love connection over Facebook with a beguiling young woman called Megan. But as their long-distance romance heats up, some things just don’t add up.
Documentarians Ariel Schulman and Henry Joost follow Nev’s journey to discover the truth behind the online lies. In 2010, what they revealed resulted in an astounding finale that proved the tip of an iceberg of internet deception. All these years later, the movie that made a franchise out of outing online deceivers may be less shocking, but the empathy with which the filmmakers approach their subjects keeps it undyingly poignant. —K.P.
How to watch: Catfish is available for rent or purchase on Prime Video.
Honorable mention: The Polka King
A great scam of the internet right now is that The Man Who Would Be Polka King can not be found for streaming (not by legal means anyway). This terrific 2009 doc unravels the crimes of a notorious performer/scammer, and it does it all from the stool of a local bar and with interviews bursting with local color. But the next best thing is this docu-drama/dark comedy that it very directly inspired.
Co-written by Maya Forbes and Wallace Wolodarsky, The Polka King pulls a lot of dialogue directly from interviews with the friends, family, and victims of Jan Lewan, a charismatic con artist who aimed to build a polka empire with other people’s money. Jack Black stars, bringing all the rock star panache you need to understand how Lewan could be so beguiling to the Pennsylvanian retirees who surrendered their savings to the self-proclaimed Polka King. Bonus fun comes in salty supporting turns of Jenny Slate, Jacki Weaver, and Jason Schwartzman. —K.P.
How to watch: The Polka King is now streaming on Netflix.
