A con artist is an accomplished actor, the star of an elaborate show staged to tease money from pockets. Chicago’s infamous Joseph Weil, known as the Yellow Kid, pulled off convincing performances—posing as bank presidents, inventors, millionaires, and even scientists—in a swindling career that spanned decades. “I have played more roles in real life,” he once declared, “than the average actor ever dreamed of.”
Like actors and movie-makers, con artists tell stories and create illusions. That’s why swindlers and their brazen schemes are the perfect fodder for the big screen. The characters are brash and larger than life (swindling aficionado David Maurer dubbed them “the aristocrats of crime”). The tales are tall, the plots intricate and absorbing. And the audience is never sure who—if anyone—is telling the truth.
Hollywood has been fascinated with the confidence trickster’s antics since the early 1920s, when a silent film character named J. Rufus “Get-Rich-Quick” Wallingford preyed on the gullible in small-town Iowa. Here are ten of the best swindler flicks—movies where the truth is elusive and make-believe steals the show.
The Sting (1973)
The granddaddy of con man movies, The Sting popularized “the wire,” an elaborate swindle that offered insider tips on race results and assured victims they were betting on a horse guaranteed to win. This is fraud on an industrial scale, complete with fake betting shops and gambling dens and a small army of con-men recruited to pose as patrons and staff.
The movie, set in Depression-era Chicago, revolves around hustler Johnny Hooker (Robert Redford), who’s determined to avenge a friend’s murder by swindling the crime boss who ordered the killing. Hooker enlists the help of veteran con man Henry Gondorff (Paul Newman), a character clearly modeled on the real-life swindling Chicago brothers Fred and Charley Gondorff.
Newman and Redford, together again after their triumph in Butch Cassidy and the Sundance Kid, are at the top of their game as they portray the con men pulling the strings. But the swindle itself is the real star of this Academy Award winner for Best Picture. The crooks are the good guys and the victim, the sneering gangster Doyle Lonnegan (Robert Shaw), is greedy, cruel and gets what he deserves. The rest of us, seduced into thinking we’re in on the con, belatedly discover we’ve been set up too.
Catch Me If You Can (2002)
Con men live “a chameleon existence,” notes Frank Abagnale, the master forger whose five-year run of lies and deceit are the subject of this biopic. Abagnale did just that, impersonating a doctor, a lawyer, an airline pilot and a university professor before he was caught and reinvented himself a final time, as a law-enforcement consultant who uses his skills to battle fraud.
Leonardo DiCaprio is pitch-perfect as the youthful con man (Abagnale was just sixteen when he began passing worthless checks—his haul eventually reached an astounding $2.5 million) and Tom Hanks nails the part of the straight-laced FBI agent on his trail. It’s a rags-to-riches-to-rags story, with a happy ending. And since most of the victims are banks, there’s no harm in rooting for the bad guy.
Dirty Rotten Scoundrels (1988)
Con games are often so outlandish that they descend into farce. Dirty Rotten Scoundrels is a classic comedy that mines the absurdity of the con for laughs.
Steve Martin and Michael Caine are con men competing for marks on the French Riviera. They make a bet: the first one to relieve a visiting American heiress (played by Glenne Headly) of $50,000 wins, and the loser leaves town. Their one-upmanship and amateurish ploys make this a hilarious, over-the-top ride to a surprise ending.
American Hustle (2013)
This caper flick, set in the 1970s and complete with big hair and wide lapels, features two small-time swindlers (played by Christian Bale and Amy Adams) forced to help federal agents catch corrupt politicians. It’s based on an FBI undercover operation launched in 1978, code-named Abscam, which led to the conviction of seven Congressmen on bribery and conspiracy charges.
In the real Abscam, a convicted con man was enlisted to create a fake company as a front for agents posing as Arab investors. Bale, Adams, and Bradley Cooper (as an ambitious but naive federal agent) give stellar performances in a movie that explores how the line between legal and illegal blurs when law enforcement officials pose as crooks – and crooks do what they do best.
Criminal (2004)
“Watch and learn.” That’s the advice small-time con man Richard Gaddis (played to street-wise, smarmy perfection by John C. Reilly) offers to younger, even smaller-time hustler Rodrigo (Diego Luna) when they team up for a day of grifting in Los Angeles.
Their hustles for chump change morph into the chance to make a killing when Gaddis gets wind of a plan to rip off a billionaire who collects vintage currency. The bait is an extremely rare and valuable (and of course, counterfeit) silver certificate. Gaddis takes control of the scam and navigates a perfect storm of roadblocks, rivalries, and greedy partners as he and Rodrigo rush to close the deal. At least, Gaddis appears to be in control—and this keeps viewers guessing until the finale reveals all.
The Brothers Bloom (2008)
Most con games end with the fraudsters richer and their victims poorer, their dreams of easy money shattered. If there’s such a thing as a perfect con, Stephen Bloom observes in this wild ride of a movie, it’s one “where everyone involved gets just the thing they wanted.”
Rian Johnson, writer and director of the delightful whodunit Knives Out, also wrote and directed this clever play on the thin line separating fact and fiction. Stephen (Mark Ruffalo) and his younger brother, with the improbable name Bloom Bloom (Adrien Brody) have been pulling cons since they were kids, and team up for one last job. The mark is a reclusive heiress (Rachel Weisz), who craves excitement and joins them for a globe-trotting adventure complete with forays into smuggling, theft, kidnapping, and faked deaths. Deception being at the heart of the genre, of course, not everything is as it seems.
The Usual Suspects (1995)
While not among the usual suspects in the con man genre, this movie is all about deception. The plot hinges on Kevin Spacey’s Oscar-winning performance as Roger Kint, the shifty and talkative survivor of a heist gone wrong. Under police interrogation, he weaves a tale of intrigue and double-cross orchestrated by a ruthless mob boss named Keyser Söze.
The truth emerges only in the final moments, after “Kint” walks free. The names and places for his convoluted story have been gleaned from odds and ends posted on a bulletin board at the police station, and the mysterious Keyser Söze has fooled everyone.
Matchstick Men (2003)
Can a con man be conned? That question—spoiler alert—drives the plot of Matchstick Men, which devotes plenty of screen time to the phobias and struggles of Roy Waller (Nicolas Cage), a clean-freak who spends more time holed up in his house than fleecing victims. His attempts to reconnect with his teenaged daughter provide further distractions as Waller’s restless, fast-talking partner Frank Mercer (Sam Rockwell) sets up a lucrative score.
Waller, like Richard Gaddis in Criminal, thinks he knows what’s going down. So does the audience. And even when the game goes sour, the train wreck that unfolds is not what’s really happening at all.
While Waller at one point calls himself a “matchstick man,” this does not appear to be a common term for a con artist (try searching it on Google—most hits circle back to the movie). It may refer to the fact that con men tend to adopt simple, two-dimensional personas, like the crude figures a child might draw. Or perhaps the movie’s title is made up, and it’s just another con-within-a-con.
The Good Liar (2019)
The latest contribution to the who’s-conning-whom genre, this is the story of aging swindler Roy Courtnay, who uses an online dating service to find his mark, the wealthy (and oh-so-trusting) widow Betty McLeish. At least, that’s where the story begins. A victim of a previous fraud bent on revenge, a burned accomplice with a score to settle, and a murder soon conspire to complicate Courtnay’s plan to plunder her fortune.
Acting royalty Ian McKellan and Helen Mirren are perfectly cast in the lead roles of this stylish game of cat-and-mouse. The backdrop shifts from London to Berlin, then back in time to pivotal events that occurred in the German capital in the chaotic years during and after World War Two. Nothing is quite as it seems, of course, and no one is who they say they are—until a lifetime’s worth of secrets and lies are finally exposed.
Ocean’s Eleven, Twelve and Thirteen (2001, 2004 and 2007)
Three films rolled into one to round out this list may sound like cheating, but hey, these movies are all about cheating. Each installment in the Oceans franchise offers a fresh take on the elaborate “long con” made famous by The Sting— the meticulously planned and professionally executed confidence game. Danny Ocean, a crook with class, assembles a dream team of fellow fraudsters, with skill-sets ranging from disguise to computer hacking, to pull off what appear to be impossible heists.
The action shifts from the casinos of Las Vegas to the capital cities of Europe and the scripts sizzle with wit and banter. George Clooney as Ocean leads the ensemble cast, along with fellow A-listers Brad Pitt and Matt Damon. Adding even more Hollywood royalty, the acclaimed Steven Soderbergh directs all three.
It’s a winning combination, a sure-thing. And that goes for all of these movies.
Trust me—would I steer you wrong?
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Dean Jobb is the author of Empire of Deception (Algonquin Books and HarperCollins Canada), the true story of a master swindler Leo Koretz, who hoodwinked the elite of 1920s Chicago with tall tales of vast oil fields in the jungles of Panama. He teaches in the MFA in Creative Nonfiction program at the University of King’s College in Halifax, Nova Scotia.
