Con artists have been popular characters for a long time in Hollywood. Some of the most loved films from Hollywood’s earliest days feature them, like The Wizard of Oz and The Music Man. In honor of that long history, here is our list of some of our favorite movies about con artists and their sneaky ways.
American Hustle
American Hustle was sometimes jokingly called “American Hair and Makeup” because of the elaborate examples of both in this movie set in the 1970s. That’s appropriate too, as the movie is loosely based on a real con set up by the FBI to nab corrupt politicians. The hair and makeup in the movie are also just a great bonus that help make American Hustle a really fun movie.
Heartbreakers
Heartbreakers is a classic con artist movie. Sigourney Weaver and Jennifer Love Hewitt play a mother-daughter team who trick men into marrying and giving up their money. It’s filled with little scams throughout, which is also a fun little bonus, and has a great twist at the end, that you’ll just have to watch the movie to find out about.
The Sting
Without a doubt, one of the best movies about grifting has to be The Sting. The superstar cast led by Paul Newman, Robert Redford, and Robert Shaw chew up the scenery in this fast-paced and delightful classic. The key ingredient in the movie is David S. Ward’s script which effortlessly explains what could be a fairly complicated con to understand on the surface.
The Wolf Of Wall Street
While The Wolf Of Wall Street may be more about the dangers of excess and ego, at its heart is the massive grift that Jordan Belfort (Leonardo DiCaprio) and his cohorts pulled off as they built their fraudulent company. Scams on Wall Street are nothing new, they just took them to a level previously unseen.
The Grifters
Any list like this is going to have to include anymore called The Grifters. The movie, starring John Cusack, Anjelica Huston, and Annette Bening as a trio of con artists plays out like a ’50s crime novel set in the early ’90s. It has a “classic” feel to it and it’s really fun.
Ocean’s Eleven
Some might call Ocean’s Eleven a heist film, and it is. But it’s also got a whole lot of grifting going on in it. Every one of the “eleven” has some hustle to their game, especially Danny Ocean (George Clooney). The smooth-talking burglar uses his wits more than his brawn to pull off their incredible heist. It makes for some incredible dialog and a some unforgettable moments.
The Greatest Showman
It might not be totally fair to call PT Barnum a con artist, but there is a reason he is associated with the famous quote, “There’s a sucker born every minute,” though he almost certainly didn’t actually say it. But as a showman, there was still a little grift in him. He just made it worth it to be to give them his money.
Boiler Room
Years before The Wolf Of Wall Street, Ben Affleck, Giovanni Ribisi, and Vin Diesel teamed up for Boiler Room about a sketchy brokerage firm running basically the same scam Jordan Belfort ran that inspired the Scorsese movie. It’s a raw look at the industry and its shifty ways.
A Fish Called Wanda
Wanda Gershwitz (Jamie Lee Curtis) isn’t the greatest grifter of all time, and her boyfriend Otto (Kevin Kline) has to be one of the dumbest ever. Teaming up with Ken and Archie (Michael Palin and John Cleese, respectively) doesn’t help them much, either. Somehow, A Fish Called Wanda has become a little bit of a forgotten classic more than three decades after its release, but it’s still wild and hilarious and we promise you won’t be DISAPPOINTED with it.
The Wizard of Lies
One of the worst, most destructive con men in history was Bernie Madoff. His decades-long con left many innocent people holding the bag. Two good happened after that. First, Madoff spent the last decade of his life having a miserable time in prison and second, HBO made a pretty darn good movie about the whole scam, starring Robert De Niro as Madoff.
Six Degrees of Separation
The movie Six Degrees of Separation is based on a play by the same, itself loosely based on the life of grifter David Hampton, who scammed money out of Manhattan socialites by convincing them he was the son of actor Sidney Poitier. That’s exactly what Will Smith’s character, Paul, does in the movie. And yep, if you’re wondering it’s the play that brought the term into the mainstream.
The Talented Mr. Ripley
Tom Ripley, played by Matt Damon in The Talented Mr. Ripley is one of the more terrifying hustlers on this list. Through the tense movie, he proves he’ll stop at nothing to get what he wants. This is not one of the “fun” movies about con artists.
Focus
Will Smith plays a con man who Margot Robbie has the misfortune of trying to con. It sets up an interesting dynamic and while it’s not the most original idea to ever come of Hollywood, its sleek production and snappy script make well worth anyone’s time.
Dirty Rotten Scoundrels
Now we come to an all-time classic. Steve Martin and Michael Caine play two con artists forced to come together to pull off some huge cons in Dirty Rotten Scoundrels and it works well…until it doesn’t and they find themselves on the other end of a grift. It’s just the best comedy about con artists ever made, and one of Steve Martin’s best movies too, don’t you agree?
The Wizard Of Oz
This is a tricky one to place on here, but there is no doubt that on the surface, the Wizard in The Wizard of Oz is a perfect example of a scam artist. He’s a pretty great one too, seeing as how he got the whole of Oz to believe his nonsense. He can’t pull one over on Dorothy though, she’s sees his scam almost immediately.
The Usual Suspects
“The greatest trick the devil ever pulled was convincing the world he didn’t exist,” says everything you need to know about Verbal Kint aka Keyser Söze (Kevin Spacey). It’s a line that sums up the entire movie in one breath. Verbal Kint is the ultimate confidence man, brimming with exactly that, confidence, after all, he pulls off his grift in the middle of a police station filled with cops looking for him.
Saltburn
Like The Talented Mr. Ripley in the ’90s, Saltburn takes things to absolute extremes when it comes to scams. Oliver Quick (Barry Keoghan) is diabolical in the planning and execution of his scam. The fact that he gets away with it only makes it that much more disturbing.
Catch Me If You Can
There’s a lot to unpack with Catch Me If You Can. The movie, with a great cast that includes Leonardo DiCaprio and Tom Hanks, is based on the autobiography of career criminal Frank Abagnale. It’s a fantastic movie that fans can watch over and over, but it may in and of itself all be a scam. There is a lot of doubt in how much of the book – if any of it – is true at all. So meta.
Matchstick Men
In Matchstick Men, Nicolas Cage plays a con artist who really has everything always going against him. It’s a look into what happens when cons go wrong, really. Like a lot of movies about grifters, we root for the criminal, and Cage’s performance and his character’s bad luck make it easy.
The Spanish Prisoner
The Spanish Prisoner is the name of one of the oldest and most widely used scams in history. The movie of the same name is basically Steve Martin’s character pulling this grift on Campbell Scott’s character. It’s the same scam that we’ve all had attempted on us by Nigerian scammers promising great wealth by helping them with a lost rich relative.
The Producers
Of all of Mel Brooks’ amazing movies, The Producers might be the one that is most surprising in how it’s endured over the years, with a wildly successful musical based on it and another movie based on the musical. In the end, the plot it just a good old-fashioned scam.
The Prestige
Magicians are, at their heart, con artists. Any great magician will admit to it. It’s how they use the power of deception that separates them from criminal grifters. That’s why The Prestige finds its way onto this list. Competing magicians fooling each other with their tricks and illusions are nothing more than scams.
Now You See Me
Now You See Me is a perfect example of magicians using their powers of persuasion and artistry for crime. The magicians in the movie use everything they’ve learned about magic and illusion to commit crimes but with a side trick of actually acting a bit like Robin Hood with the ill-gotten gains. It’s complicated, but that’s what makes it great.
Curly Sue
Kids have been used in deceptions for centuries and in the movies we’ve seen it with movies like Curly Sue. It’s a classic grifter movie, with James Belushi playing the most stereotypical con man of all time. And yet, the movie still works really well. Sure, it’s a bit dated, but hey, keep a sharp eye for a young Steve Carell, who made his film debut here.
Leap Of Faith
It turns out Steve Martin has a real knack for blaming scam artists. In Leap of Faith, he plays one of the oldest versions of a grifter on earth – the religious type. Martin stars as Jonas Nightengale, a con man who discovers that he can make serious money by pretending to be a faith healer, using every trick in the book to separate desperate people from their money.
I Love You Phillip Morris
I Love You Phillip Morris is really a love story, but it’s about a con man who is so in love with Phillip Morris he can’t stop scamming people or breaking out of jail to be with him. Jim Carrey’s performance as Steven, the con artist is one of the most underrated of his stellar career.
The Good Liar
Romance scams, like the one in The Good Liar, are as old as time. When it’s Ian McKellen playing the grifter though, you know it’s worth checking out. He’s just so perfect in the role of an aging hustler running his scam on a widow (Helen Mirren).
The Frighteners
Director Peter Jackson’s The Frighteners is a different kind of grifter movie. The main character, played by Michael J. Fox runs his scams with the help of a few ghosts that only he can see. It’s honestly one of the most underappreciated movies by Jackson with fantastic performances all around.
The Music Man
If you’ve never seen The Music Man, but you’re a fan of The Simpsons, you are more familiar with the plot that you may be aware. One of the best Simpson’s episodes of all time has to be “Marge Vs. Monorail” and it’s basically all based on The Music Man. In the movie, the “Man” isn’t selling a monorail, but he is selling the town a scam with his words and his songs.
Maverick
Mel Gibson has a few forgotten hits, and Maverick is a great example of one that should be better remembered. Gibson plays a gambler and card sharp in late 19th Century America on his way to play in a poker tournament but finds plenty of ways to hustle on the way.
White Men Can’t Jump
Billy Hoyle (Woody Harrelson) sure knows how to hustle guys on the basketball court. He quickly becomes Sidney Deane’s (Wesley Snipes) nemesis on and off the court. That is, until the two team up to hustle for even more money.
Trading Places
While Trading Places is strictly about con men, the con that Billy Ray Valentine (Eddie Murphy) and Louis Winthorpe III (Dan Aykroyd) team up to pull on the Duke Brothers at the end surely makes it worthy of addition to this list. Like many on the list, it’s really easy to root for the ones pulling the scam.