Underrated Movies About Real-Life Scammers And Con Artists

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Vote up the movies that sweep you up in a real-life scam.

Catch Me If You Can and American Hustle are two of the best-known movies about real-life con artists. If you've seen them but crave more fact-based scam films, try one of these underrated titles. The subject of scamming has long fascinated audiences, likely because it plays into a couple primal emotions simultaneously. We admire the ingenuity and creativity that goes into devising these schemes, yet at the same time, we loathe the idea of amoral scammers ripping off and deceiving other people. Such cognitive dissonance makes it easy to get sucked in.

Many big stars appear in the following movies. Among them are Melissa McCarthy, Jim Carrey, Jennifer Lopez, and Robert DeNiro. In each case, the stories provide a captivating look at how true cons were carried out and what the consequences were for the parties involved. They turned to some ethically dubious individuals for inspiration, making great art out of crimes that were often shocking.

  • In I Love You Phillip Morris, Jim Carrey plays Steven Russell, a former cop who decides his life needs a radical change following a car accident. He comes out of the closet, leaves his wife, and, oddly, starts pulling credit card scams in Florida. He's sentenced to jail for that last part, which is where he meets and falls in love with Phillip (Ewan McGregor). But even Phillip isn't immune from his scams. At one point during which they're separated, Steven convinces his lover via phone call that he's dying of AIDS. The movie offers an insightful exploration of compulsive lying and the mindset that makes the character so intent on pulling off one deception after another. Carrey shows a different side of his immense talents here, mixing his dramatic and comedic abilities in a unique manner, ensuring we care about this guy even if we don't exactly like him.

    Steven Jay Russell is currently serving a 144-year jail sentence for a stunning series of crimes ranging from insurance fraud to falsely passing himself off as a judge. He's also escaped from jail four different times. The driving force behind those escapes was a desire to be with the love of his life, Phillip Morris, a man he met while they were behind bars together. When Russell wasn't in jail, he embezzled $800,000 to spend on creating a lavish lifestyle for them to enjoy. The movie captures the unusual core of the true story, which is that love was the factor that drove many of Russell's crimes. 

    84 votes

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  • Melissa McCarthy earned an Oscar nomination for a rare dramatic role in Can You Ever Forgive Me? She plays Lee Isreal, a professional biographer whose career has taken a substantial hit, thanks to an alcohol problem, a bad attitude, and a desire to write about non-commercial subjects. Desperate for cash, she starts forging letters, alleging they were penned by great authors, then selling them on the collectibles market. Richard E. Grant is Jack, a fellow alcoholic who helps her as the authorities close in. With McCarthy at the helm, the movie is gripping for two reasons. First, it's a well-told story about a woman whose desperation drives her to engage in a very risky scam. Second, the character surprisingly doesn't feel much remorse for her actions. People were reading - and paying for - her writing, and in her mind, that's more than enough justification for the con. 

    The real Lee Isreal was a literary forger desperate for cash to pay her rent and afford treatment for her sick cat. She therefore faked letters, claiming they were written by the likes of Noel Coward, Fanny Brice, and Dorothy Parker, then peddled them around New York's bookstores. Although she didn't get rich doing so, Isreal made a fair amount of cash from the scheme, while undermining the integrity of the literary memorabilia market. Some would argue she got a slap on the wrist for her offenses. Isreal, who openly expressed pride in her writing, was sentenced to six months of house arrest and five years' probation.

    49 votes
  • 3
    46 VOTES

    Big Eyes tells a pretty wild true story. Amy Adams plays Margaret Keane, an aspiring painter who creates hypnotic portraits of big-eyed waifs. Her husband Walter (Christoph Waltz) is a painter, too. Because Margaret signs her work with only her last name, people mistake her creations for his. Instead of setting the record straight, he takes credit for it. Before long, he's got Margaret working overtime to crank out more paintings, as he executes a business plan that makes them wealthy while also making her feel resentful. Directed by Tim Burton, Big Eyes shows Walter's narcissism and manipulativeness in fascinating detail. More than that, though, it's a rousing story about how Margaret finds the strength to stand up for herself and reclaim her art. Positioned as awards bait in 2014, the movie was unfortunately crowded out by the competition, coming up short with awards bodies and at the box office. 

    In real life, Walter Keane was, to put it mildly, a real piece of work. He asked his wife to teach him how to paint the big-eyed characters, and when he couldn't do it, laid the blame at her feet. He then literally kept her locked away in the beautiful home her paintings bought, where she toiled endlessly on stuff that he fraudulently passed off as his own. Because he controlled their finances, Margaret never saw a penny of the money she technically earned. When the two finally divorced, she blew the lid off the whole scam, even challenging him to a “paint-off” in order to prove herself the true artist. Walter unsurprisingly refused to participate. 

    46 votes

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  • Will Smith shook off his Fresh Prince persona with a dramatic turn in 1993's Six Degrees of Separation. He portrays Paul, a young Black man who charms his way into the lives of a rich white couple, Flan (Donald Sutherland) and Ouisa (Stockard Channing) Kittridge. He does this, in part, by claiming to be a friend of their Ivy League children, but also the son of famed actor Sidney Poitier. They let him stay in their lavish home, even giving him spending money. Paul's cover is blown when he brings a hustler home one night, so the Kittridges kick him out. They soon learn that he has pulled this exact same scam on others. Smith shows the beginning of the dramatic abilities that would eventually win him an Oscar. Six Degrees of Separation is additionally a poignant story about how this man strives to leech off people far wealthier than he is. 

    The real Paul was David Hampton, a guy from Buffalo, NY who yearned to be part of the elite social scene in Manhattan. He lied, telling people he was Sidney Poitier's son, an act that quickly opened doors. A Columbia University dean and a TV station executive were among those he fooled. His benefactors lavished him with money, clothing, and other gifts. Eventually his scam was revealed, and it turned out he had a fairly lengthy arrest record. Hampton died of AIDS in 2003.

    20 votes

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  • 5
    41 VOTES

    Compliance is a film guaranteed to get under your skin and completely unnerve you. Becky (Dreama Walker) is a fast-food worker who has been accused of stealing money from a customer. Her manager, Sandra (Ann Dowd), is determined to get to the bottom of things. She talks to a police officer, who identifies himself as “Officer Daniels," on the phone. He tells her what to do, but his commands become increasingly uncomfortable and invasive for Becky. A strip search is part of it. Sandra starts having doubts about him, but believing he really is a law enforcement officer, she continues to comply, despite the little voice in her head telling her something is wrong. The movie is taut and tense, and it speaks to how individuals are prone to doing bad things when ordered to by someone with a position of authority.

    If Compliance sounds far-fetched, it's not. Writer/director Craig Zobel based it on a 2004 incident. A Florida prison guard, apparently feeding into some bizarre kinks, pretended to be a cop and called a McDonald's restaurant, then ordered a manager and her fiancée to detain, strip-search, and sexually assault a female employee. Astonishingly, the caller was acquitted at trial, while the manager received a year of probation. Only the fiancée got a stiff punishment, as he was the one who performed the assault. For his role, he got five years in jail. The employee settled with McDonald's for an unknown amount of money. 

    41 votes

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  • 6
    28 VOTES


    Photo: STX Films

    Hustlers was a box office hit and got rave reviews, and yet people still underrate its quality. That's how good it is. Destiny (Constance Wu) and Ramona (Jennifer Lopez) are strippers whose clientele tends to be rich Wall Street types who frequent the club where they work. When the 2008 stock market crash occurs, their industry goes belly-up. Desperate for cash, Ramona comes up with a scheme to rip off those wheeler-dealers by seducing them, getting them intoxicated, and encouraging them to max out their credit cards at the club. Before long, they and their colleagues are flush with more cash than they know what to do with. The first time you see Hustlers, it's easy to be wowed by the edgy nature of the film, the sexual content, and the thrill of seeing the women triumph over the amoral stockbrokers who caused the crash. See it again, though, and you notice what a sharply written, skillfully made film it is. In other words, it's even better than you remember. 

    The movie takes a few small liberties with the true story, yet certainly remains true to its spirit. Ramona is based on Samantha Barbash, a gentleman's club hostess who devised a “fishing” scheme with cohort Roselyn Keo (the inspiration for Destiny). As seen onscreen, they used their sexuality to lure wealthy contacts to a meeting, got them drunk or high on ecstasy, then took them to the club to wear out their credit cards. This scheme netted them as much as $100,000 per night. Eventually, the women were busted, with Barbash getting five years' probation and Keo avoiding significant punishment via a plea bargain.

    28 votes