Everybody loves big, intricate caper films like Ocean’s Eleven, but there is also something to be said about the small-time hustlers who will look you in the eye and smile while they take your money. These small cons include short cons that happen within a few hours and the long cons that may take place over weeks, months, or even years.
These grifters have honed their craft and keep audiences on edge as they try to follow their crimes. These movies and their morally ambiguous leads may not be as extravagant as some of their counterparts, but they are just as interesting.
10 ‘The Talented Mr. Ripley’ (1999)
Tom Ripley (Matt Damon) is an average piano player in New York who wants to be someone else: an opportunity presents itself to do just that. When the father of Dickie Greenleaf (Jude Law) mistakes Tom for a Princeton classmate of his son, he sends him to Italy with $1000 to go and retrieve the rakish, irresponsible ex-pat living off his family’s wealth.
From forging passports to an uncanny ability to replicate any voice he’s ever heard, Tom is the kind of small-time con that can be very dangerous. Unassuming and winsome, he can earn your trust in a flash, but a violent and insecure crook lies beneath the charm.
9 ‘The Grifters’ (1990)
John Cusack, Annette Bening, and Angelica Huston have never been better than they were in this flick about deceit, short and long cons, and dysfunctional family dynamics. Raised by a small-time con artist named Lily (Huston), Roy Dillon (Cusack) has a healthy distrust for just about everyone and everything. As he should: he is also a con who has a bag of tricks ranging from a $20 bill bar trick to several thousand dollar swindles.
The worst thing for a young grifter like Roy is to run into a beautiful femme fatale like Myra Langtry (Bening), who is just as conniving as him. From picking other people’s pockets to protecting his own, Roy gets into a mess when he takes Lily, who is on the lam from a mobster and gets tangled up with Myra, who is playing a confidence game of her own.
8 ‘The Brothers Bloom’ (2008)
There’s a saying that “blood is thicker than water.” In The Brothers Bloom, brothers Stephen (Mark Ruffalo) and Bloom (Adrien Brody) have been hustling since they were just boys being shipped from one foster home after another. After 20-plus years of small cons, Bloom wants out of the family business, but Stephen convinces him to stick around for one last big score.
Sometimes, the heart wants what the heart wants, and when the mark is a beautiful big city heiress like Penelope Stamp (Rachel Weisz), Bloom can’t help but fall for her. Ruffalo, Brody, and Weisz are gifted players who collaborate with director Rian Johnson to execute a fun movie with the energy of five films. While a financial flop, this movie is an indie classic you shouldn’t miss.
7 ‘The Color of Money’ (1986)
In The Color of Money, the Mission Impossible star Tom Cruise is a brash and unflinchingly irreverent young pool shark named Vincent Lauria: he’s a natural but lacks the know-how to turn it into real money. Enter the salty and well-traveled hustler Mr. Eddie Felson (Paul Newman). Together, there’s a boatload of cash to be made, but Vincent must put his ego aside and learn to trust Eddie as a mentor and not a con man himself.
Newman, in particular, is dazzling with this late-career performance, showing off his charm and effortless smile. It’s a must-watch for cinephiles who want to see two true stars from separate generations click to the tune billiard balls being racked. As if there wasn’t enough star power behind this movie, Martin Scorcese directs in what is perhaps his most underrated movie.
6 ‘Nightmare Alley’ (2021)
Horror legend Guillermo Del Toro brings his unique, macabre style to the story of a sideshow carnie, who gets in way over his head with the ultimate femme fatale. Nightmare Alley is a well-crafted story of betrayal and greed that features two of the best performers in the business, Bradley Cooper and Cate Blanchett, as Stan Carlisle and Dr. Lillith Ritter.
The duo enters a neo-noir-esque romance that becomes more than it is when the small-time charlatan Stan realizes that he’s being played. Del Toro weaves an intriguing story using his trademark haunting tone blended with a harrowing tale you can’t take your eyes off.
5 ‘Paper Moon’ (1973)
Cerebral filmmaker Peter Bogdanovich is behind the camera to tell the story of slick 1930s con artists Moses “Moze” Pray and Addie Loggins (played by the real-life father-daughter duo of Ryan and Tatum O’Neal). The pair is drifting their way through the Midwestern countryside, pulling a series of short cons on unsuspecting country folks.
But when Moze tries to play Addie for a mark, she turns the tables and forces him to take her on as a permanent partner. Everything is going well until the unlikely pair tries to get over on a sultry burlesque dancer named Trixie Delight (Madeline Kahn), who has the backing of a ruthless bootlegger. It’s an excellent period piece and follow-up to the 1971 masterpiece The Last Picture Show that put the late Bogdanovich on the map.
4 ‘American Hustle’ (2013)
One of American Hustle‘s most identifiable features is its A-list cast. Bradley Cooper stars with Jennifer Lawrence, Christian Bale, Amy Adams, Jeremy Renner, and Robert DeNiro in the story about small-time can man Irving Rosenfeld (Bale) and his eccentric wife Rosalyn (an Oscar-winning performance from Lawrence).
The couple’s rocky marriage struggles to survive after being arrested and made informants for the FBI agent Richie DiMaso (Cooper). Renner is the brash mayor of a small New Jersey town who gets caught up in a crazy scam created by Irving and the FBI to bring down mobsters. It’s a whirlwind of movie goodness and one of the best con movies ever made.
3 ‘Catch Me If You Can’ (2002)
Leonardo DiCaprio plays real-life con man Frank Abagnale in Steven Spielberg‘s Catch Me If You Can. Tom Hanks is the agent charged with tracking down the bold forger/grifter who likes to impersonate commercial plane pilots and medical doctors. Abagnale may be the most prolific small-time con artist who ever lived, and DiCaprio is excellent in the film.
He manages to stay one step ahead of FBI agent Carl Hanratty (Hanks), who is dogged in pursuing the man who managed to forge thousands of fake checks to the tune of more than $3 million in the 1960s while treating himself to the finest things in life. The movie features iconic performers clicking at the top of their game and being guided by arguably the finest director of the modern era: that’s a recipe for a great cinema.
2 ‘Matchstick Men’ (2003)
Director Ridley Scott is considered a sci-fi visionary, but his reach also extends to many other genres. Matchstick Men is set in Las Vegas to a snappy soundtrack that stars Nicolas Cage and Sam Rockwell. It’s a wonderful neo-noir piece that takes the audience on a ride as a couple of small-time con artists named Roy Waller (Cage) and Frank Mercer (Rockwell) who scam unsuspecting suckers with bogus identities and contests over the phone.
It’s a great racket but time-consuming, and the stakes aren’t that big. Roy suffers from OCD and is reticent to pull long cons, but Frank is always in his ear, and eventually, the two step up their game for more cash. When Roy’s daughter Angela (Alison Lohman) enters the picture, things get very sticky for the “matchstick men.”
1 ‘Dirty Rotten Scoundrels’ (1988)
One of the best and funniest movies ever made, Dirty Rotten Scoundrels tops or countdown. The chemistry between Steve Martin, Michael Caine, and Glenne Headly makes this movie pop off the screen. Martin has never been better than petty swindler Freddy Benson, who teams up with the more polished and experienced Lawrence Jamieson (Caine) to put together a long con on Janet Colgate (Headly), who they believe to be the heir to the Colgate toothpaste fortune.
The hijinks that ensue over the almost two-hour runtime are a beautiful blend of comedy, romance, and cat-and-mouse tomfoolery that truly brings out the talents of all three performers in the best way. It even has a tremendous twist ending that punctuates one of the best times you can have at the movies.
