The Art of the Dirty Deal: 17 Movies, Shows, and Documentaries About Scams (2024)

The Art of the Dirty Deal: 17 Movies, Shows, and Documentaries About Scams (1)

Scamming is so hot right now. The confidence arts have been lighting up Hollywood, and networks and streamers are practically overflowing with content about grifters, fraudsters, and gougers. This year alone, scam-hungry viewers have been served Inventing Anna, The Tinder Swindler, WeCrashed, Super Pumped: The Battle For Uber, The Dropout, Worst Roommate Ever, Bad Vegan, and The Thing About Pam.

That might seem like a lot — and it is for just a few months of programming — but the truth is that scams and grifters have inspired films, shows, and documentary projects for years. If you’re one of those people who can’t get enough of the twisted justifications of Elizabeth Holmes or who loves a look behind the pyramid-scheme curtain, here are 17 more shows, movies, and documentaries to check out.

Art And Craft (2014)

A critically acclaimed 2014 documentary about one of the most staggeringly prolific art forgers in history, Art And Craft follows the 30-year career of Mark Landis, who spent years knocking off everything from renaissance masters to Walt Disney. The twist? He didn’t do it for the money — at least, not for the money for himself. Instead, Landis donated many of his works to noted art museums and institutions, inviting them to either display the works or pawn them off to pad their coffers. He eventually got caught, of course, but not until his work had been unknowingly seen by thousands who marveled in its grace and beauty.

Stream this scam: Kanopy, CuriosityStream, PlutoTV, and Topic

Can You Ever Forgive Me (2018)

Melissa McCarthy and Richard E. Grant deliver a one-two punch of great acting in Can You Ever Forgive Me, a movie from 2018 about another famed forger, Lee Israel. Known for her smart and intimate faux-letters purported to be written by long-gone celebrities and literary figures, Israel used her “art” to support herself for a good part of the early ’90s. Can You Ever Forgive me roughly traces that path, giving viewers a glimpse at how McCarthy’s Israel hits rock bottom before finding a false sense of fame and security through her work.

Stream this scam: Amazon Prime Video (rent/buy)

Catch Me If You Can (2002)

Leonardo DiCaprio just loves a con man. In Catch Me If You Can, his first of two movies on this list, DiCaprio plays Frank Abagnale Jr., a wily teenager who managed to pose as a doctor, lawyer, and jetliner co-pilot before he was even eligible to vote. Pursued in this movie by Tom Hanks’s FBI agent Carl Hanratty, Abagnale Jr. used his forgery skills to pass bad checks — remember, this all takes place in the ’60s, when you could do that sort of thing — ultimately netting boatloads of bucks from banks. The FBI lands their man, of course, but there’s a postscript: After prison, Abagnale Jr. ended up living a long and productive life working as one of the world’s most preeminent experts on fraud. Who said crime doesn’t pay?

Stream this scam: Amazon Prime Video (rent/buy)

Dirty John season one (2018) and Dr. Death (2021)

Two teeth-grindingly uncomfortable (in a good way) series inspired by podcasts, Dirty John and Dr. Death cast Eric Bana and Joshua Jackson, respectively, as medical professionals withmega-problems. Dirty John’s first season was birthed from an Los Angeles Times podcast that told the story of the manipulative and vindictive John Meehan, who glommed on to a woman named Debra Newel (Connie Britton). They eventually married, despite the objections of her children, and then the wheels started to come off. The results are terrifying and tragic and should make anyone question how far they’d go to truly believe a lie.

Dr. Death, on the other hand, is about a catastrophic failure of a different sort. First detailed in a Wondery podcast, Dr. Death follows Jackson’s Dr. Christopher Duntsch, a Texas neurosurgeon who’s believed to be the next big thing until he isn’t. Refusing to accept his own failures, Duntsch pushes on, injuring and maiming countless patients in truly awful-sounding surgeries. The worst part? Hospitals continue to give him privileges, and Duntsch soldiers on. He’s ultimately taken down by a team of doctors played by Alec Baldwin and Christian Slater (who’s also in Dirty John season two, incidentally) and a spitfire lawyer played by AnnaSophia Robb, but not before severing his trusting best friend’s spinal cord.

Stream these scams: Dirty John is on Netflix; Dr. Death is on Peacock.

The Eyes Of Tammy Faye (2021)

Starring Jessica Chastain in the role that nabbed her an Oscar, The Eyes Of Tammy Faye is a fresh-out-of-theaters movie inspired by the lives of televangelists Jim and Tammy Faye Bakker. Fueled by the power of the lord, Chastain’s Tammy meets, falls in love with, and rises to prominence alongside Andrew Garfield’s Jim Bakker. Coated in an increasingly heavy shellacking of makeup, Tammy struggles to go along to get along in the evangelical world, only to eventually find out that Jim has both been unfaithful in their marriage (and to God) and bilked their beloved supporters out of millions of dollars. There’s debate, of course, over how much Tammy knew or chose to ignore, but Jim did ultimately end up spending a significant amount of time in jail for his crimes.

Stream this scam: HBO Max

Fyre Fraud (2019) and Fyre: The Greatest Party That Never Happened (2019)

Arguably the documentaries that sparked streaming’s recent scam-mania, Fyre Fraud and Fyre: The Greatest Party That Never Happened track the inception, execution, and catastrophically hilarious failure of the Fyre Festival. A supposed luxury music festival in the Bahamas that went viral in 2017 for just how awful it actually was, Fyre Festival was emblematic of the occasional emptiness of influencer culture and lifestyle marketing. While both documentaries follow the festival’s foibles — including but not limited to Ja Rule, bird shit, bounced checks, barely veiled racism and colonialism, FEMA tents, and sad cheese sandwiches — they’ve also each got their own merits and flaws. If you want the full picture of what went down, watch both and attempt to parse it for yourself.

Stream these scams: Fyre Fraud is on Hulu; Fyre: The Greatest Party That Never Happened is on Netflix.

Hustlers (2019)

Yes, Hustlers is about stripping, but it’s really about so much more than that. Jennifer Lopez and Constance Wu star in the 2019 movie inspired by a New York magazine article by Jessica Pressler, who also wrote the piece that inspired Inventing Anna. (She knows scams!) The women-on-top escapade is a tale of drunk assholes and stolen credit cards — until, of course, everything goes too far and it’s no longer fun. Even the most justified scam must go a little awry in the end, after all.

Stream this scam: Hulu

I Care a Lot (2021)

Hate old people? Then I Care a Lot is for you. The fictional but feasible black comedy stars Rosamund Pike as Marla Grayson, a bobbed, cutthroat figure who has made her fortune by exploiting the elderly. After identifying a wealthy target, she has the court declare them legally incompetent, naming her their legal guardian. She throws them in a substandard assisted-living facility, empties their accounts and liquidates their assets, and then basically waits for them to die. Unfortunately for Grayson, she picks the wrong target in Dianne Wiest’s Jennifer Peterson, who is apparently the secret mother of a crime lord played by Peter Dinklage. A legal back-and-forth ensues, followed by round after round of scheming one-upmanship. It’s deliciously devious, as long as you don’t really think about how often this probably happens to people in real life.

Stream this scam: Netflix

The Inventor: Out for Blood in Silicon Valley (2019)

The documentary that introduced much of the world to the cult of the monotone personality known as Elizabeth Holmes, The Inventor: Out for Blood in Silicon Valley details the onionlike layers of scammy bullshit laid out by Holmes over the course of her career. Watching the documentary, it’s hard to imagine how anyone ever fell for Holmes, and yet hundreds if not thousands did, including people behind some of the biggest VC companies in Silicon Valley. It’s no wonder Holmes was recently convicted of fraud and faces up to 80 years in prison.

Stream this scam: HBO Max

LuLaRich (2021)

Another documentary from the makers of Fyre Fraud, LuLaRich takes something seemingly innocuous — colorful, comfortable leggings — and exposes the broad and incredibly depressing pyramid scheme behind one of the garment’s biggest boosters. The doc lifts the proverbial curtain on not just the pervasive nature of multilevel marketing schemes, especially among women, but specifically goes after LuLaRoe, a women’s clothing company that went from making $1 billion in 2016 to being named in a massive class-action lawsuit in 2017.

Stream this scam: Amazon Prime Video

McMillions (2020)

Any cultural connoisseur worth their salt knows about McDonald’s Monopoly. The fast-food restaurant’s annual “collect ’em all” game dangles big prizes by encouraging customers to collect more game pieces by buying more food. As it turns out, though, a lot of the game’s biggest prizes were practically unwinnable from 1989 to 2001, a fact that’s colorfully elucidated throughout the McMillions docuseries. Over six episodes, the series uses insider interviews to get at the ridiculous bumbles and turns that led to one of the game’s creators bilking the supposedly unriggable system for about $24 million. Anyone hungry for scam programming will surely be able to make a meal of this delicious and ridiculous case of fraud.

Stream this scam: HBO Max

Operation Varsity Blues: The College Admissions Scandal (2021)

It seems like almost yesterday that the world found out about Lori Loughlin and Felicity Huffman paying some dude to get their respective kids into college. They’ve since been in and out of prison for their crimes, all of which are detailed in Operation Varsity Blues. A mixture of documentary and reenactment, the film stars Matthew Modine as Rick Singer, the man who acted as the kingpin of the whole operation and who now faces up to 65 years in jail after helping what he estimates to be about 750 kids bilk their way — whether they knew it or not — into impressive colleges and universities. If you know the story, the documentary doesn’t break a ton of new ground, but that doesn’t mean it’s not a solid watch all the same.

Stream this scam: Netflix

Queenpins (2021)

Though it comes off like a wacky comedy starring The Good Place alums Kristen Bell and Kirby Howell-Baptiste, Queenpins is actually inspired by the true story of three Arizona women who ran one of the largest counterfeit-coupon fraud operations in U.S. history. In real life, the women managed to take corporations and businesses for tens of millions of dollars, and Queenpins doesn’t stray far from reality in that respect. Where it does go awry is in the film’s story, which relies too much on lowbrow humor and ridiculous situations to move the plot along when really the reality of the scam would have been entertaining enough.

Stream this scam: Fubo TV, Paramount+, Showtime, and DirecTV

The Wizard Of Lies (2017)

The stars aligned to make The Wizard Of Lies, a prestige HBO biopic about the late Bernie Madoff, scam king of New York. Robert De Niro stars as Wall Street impresario Madoff, who wooed New York’s elite with wife Ruth (Michelle Pfeiffer) for almost 50 years before it was revealed in 2008 that his empire was actually a massive Ponzi scheme — the biggest in history, actually. Exposing Madoff led to multibillion-dollar losses on Wall Street, and the fraudster was sentenced to what essentially amounted to life in prison. It’s not De Niro’s best work, but Madoff is a fascinating confidence man, especially considering the wealth and stature he somehow managed to achieve.

Stream this scam: HBO Max

The Wolf of Wall Street (2013)

Speaking of Wall Street: Leonardo DiCaprio once again stars as a charismatic fraudster in The Wolf of Wall Street, which dramatizes the real-life rise and fall (and rise again) of stockbroker Jordan Belfort. A penny-stock schemer who specialized in pump-and-dump operations, Belfort lived the good life alongside pal and business associate Donnie Azoff (Jonah Hill) before flaming out spectacularly in the late ’90s after the Steve Madden IPO, of all things, put federal investigators’ spotlight on the pair’s business dealings. DiCaprio and Hill are incredibly believable as scumbags, as well as incredibly entertaining.

Stream this scam: Paramount+ and Pluto TV

  • The Grifters Have Come for Your TV
  • The Dropout Hits the Scammer Sweet Spot
  • WeCrashed Disrupts Nothing
The Art of the Dirty Deal: 17 Scam Movies, Shows, and Docs

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The Art of the Dirty Deal: 17 Movies, Shows, and Documentaries About Scams (2024)
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