There’s few types of film that delight as consistently as the con man (or woman) film, and that’s why we’re going to dedicate the totality of this article to talking about some of the best con films of all time, period. It goes without saying that we’d love nothing more than to slot television’s White Collar somewhere on this list, as Matt Bomer’s Neal Caffrey is one of entertainment’s most iconic con men; unfortunately, we’ve reserved this list for films only, and as such we’ll have to leave fiction’s best looking grifter off this list. But fear not, readers, because we’ve got a laundry list of films comprised of a whole gang of con men, scoundrels and thieves for you to peruse, and we’ve no doubt you’ll be able to find something on here that suits your interests. These grifters are suave, they’re charming and they’ve got their eye on your money; be sure to keep it close when watching any of the 10 greatest con man movies in cinema history.
10. The Producers (1967)
Written and directed by Mel Brooks, one of history’s most hilarious individuals and the man that brought you gems like Blazing Saddles, Young Frankenstein and Robin Hood: Men in Tights, The Producers is a perfect mix of oddball comedy and clever con man schemes, and its cultural status as a classic con man movie make it the perfect candidate to kick off our list of cinema’s most notorious thieves. The Producers, which stars Gene Wilder and Zero Mostel as two sneaky individuals who deliberately plan to produce an awful Broadway play in order to fleece the investors out of wads of cash. Their plan goes awry when, much to their chagrin, their awful play turns out to be a smash hit, and they’re left trying to complete their grift with these unexpected new circumstances in play. It’s quintessential Mel Brooks comedy, and with Wilder and Mostel on board in some of their most impressive and iconic roles, there’s little reason to wonder why this is one of the most critically acclaimed comedies in movie history.
9. The Brothers Bloom (2008)
This underrated con man film was released in 2008 and was written and directed by Rian Johnson (whose since moved on to bigger things, like Looper and the Star Wars franchise). The Brothers Bloom, which starred Adrian Brody and Mark Ruffalo as the titular brothers, the world’s most notorious con men capable of pulling off incredibly elaborate and profitable schemes, also starred Rachel Weisz as an eccentric and wealthy heiress whom the brothers target in one of their schemes. A critical success which was not commercially successful, The Brothers Bloom remains a quirky little con movie with a good deal more heart than one might expect from a film about swindlers and the like; indeed, as many reviewers noted, there’s a bit of Wes Anderson-esque play about the film, and it brings a welcome freshness to a genre that can so often be occupied by the morally bankrupt. One of the lesser known films on this list, The Brothers Bloom is a worthwhile watch for anyone looking for a little something different with their thieving.
8. Rounders (1998)
Rounders isn’t explicitly a con movie; rather, it’s a film about poker, but there’s a good deal of trickery going on over the course of the movie, so much so that we decided it deserved a spot on this list. Rounders, which was released in 1998 and stars Matt Damon, Edward Norton, John Malkovich and Famke Janssen, sees Damon and Norton playing two young poker sharks who routinely clean up around the table; however, when one of them gets in too deep with a questionable character (played by John Malkovich, in the deliciously campy role of Teddy KGB), it’s up to the other to help him win his way out. The definitive movie on poker, Rounders plays fast and loose with the cards and it makes for some exciting (if superficial) cinema, and there’s a certain ease about both Damon and Norton that makes the whole affair feel as though maybe we, the audience, are being conned as well.
7. The Grifters (1990)
We long for the days when John Cusack was a verifiable leading man, and films like 1990’s The Grifters don’t do much to ease our grief. The Grifters, directed by Stephen Frears and starring Cusack, Anjelica Houston and Annette Benning, is based on one of literature’s most famous con man novels, Jim Thompson’s book of the same name. The film sees Cusack’s Roy Dillon, a small time grifter who dreams of bigger things, attempting to navigate the divide between his mother (Huston) and his girlfriend (Benning), both of whom are schemers in their own right and have designs on what exactly Roy’s going to be doing in his future. Nominated for four Academy Awards (including Best Director, Best Actress in a Leading Role and Best Actress in a Supporting Role), The Grifters was both a critical and commercial success that is rarely cited among the genre’s greatest films; however, we’re of the mind that it certainly warrants a place near the top of that list, if only to watch Cusack charm his way through this incredibly tense situation that we’re sure some readers can sympathize with.
6. Matchstick Men (2003)
We long for the days of Cusack, and also for the days when Nicholas Cage wasn’t a running joke in Hollywood, but rather one of the industry’s most diverse and talented leading men. While that may seem like a long, long time ago, it really wasn’t; as recently as 2003, Cage was delivering standout performances in movies like Matchstick Men, a Ridley Scott-directed film (Really? Ridley?) that also starred Alison Lohman and Sam Rockwell. Matchstick Men, which sees Cage star as an obsessive compulsive con man who, in the middle of a long con with his eccentric and charismatic partner (Rockwell), finds out he has a daughter (Lohman). It’s a nifty little wrench to throw into the classic con man duo narrative, and the presence of the young girl brings a good deal of heart into what could have been a suave but simple grift film. With stellar turns from all three leads (Rockwell in particular is magnificent, as he always is), Matchstick Men is a genre film that elevates itself by sheer force of performance and some slick maneuvering behind the camera.
5. Ocean’s Eleven (2001)
There’s a fine line between con film and heist film (as we’ll soon find out with the rest of the films on this list), but we’re going to allow the blurring of some lines and put a movie like Ocean’s Eleven on this list. The Steven Soderbergh-directed movie starred an exhaustive list of A-list Hollywood talent including George Clooney, Brad Pitt, Matt Damon, Julia Roberts, Andy Garcia, Casey Affleck, Bernie Mac and Don Cheadle. Ocean’s Eleven, which sees a former thief coming out of retirement to rob the casino of his ex-wife’s new lover (with the help of approximately 10 friends), was a critical and commercial success, and its easy charm and breezy plot helped to convince us it belonged on this list. They say con men make their living off a good smile, and who has a better one than Clooney?
4. A Fish Called Wanda (1988)
Another film that blurs the line between con film and heist film, A Fish Called Wanda was released in 1988 and stars John Cleese, Jamie Lee Curtis, Michael Palin and Kevin Kline as a group of con men who have recently stolen a large amount of jewels. But the real fun begins when the group members attempt to con each other out of sharing the loot. Written and directed by Cleese (fresh off the rush of Monty Python and the like), A Fish Called Wanda was a massive commercial and critical success, resulting in an Academy Award win for Kline (Best Supporting Actor) and for Cleese for Best Original Screenplay. A film that’s equal parts funny, thrilling and intelligent, A Fish Called Wanda is a slick movie that can be enjoyed by even the most stubborn of filmgoers.
3. Dirty Rotten Scoundrels (1988)
Between A Fish Called Wanda and Dirty Rotten Scoundrels, the Frank Oz-directed film which starred Steve Martin and Michael Caine as a pair of competitive grifters set on the same mark, 1988 was a very good year for con movies. We’re firm believers that the world is in dire need of more Steve Martin, and Dirty Rotten Scoundrels is a great place to start when looking into the comedian’s lesser known but still hilarious films. The movie sees Martin’s brash, impulsive young con man competing for the affections of a wealthy heiress against Caine’s suave, elderly con man. It’s a recipe for gleeful disaster and unlimited shenanigans, and the audience is never disappointed when two actors of this caliber go toe-to-toe in a movie about confidence schemes. It’s wonderful stuff, and an underappreciated film that was well-received by audiences and critics alike.
2. Catch Me If You Can (2002)
Were this a list comprising the best con men in cinema history, Leonardo DiCaprio’s portrayal of real life con man Frank Abagnale would undoubtedly top the list. Charming, intelligent and impossible to pin down, Abagnale is the quintessential con man and the star of Catch Me If You Can, the 2002 film directed by Stephen Spielberg and starring DiCaprio, Tom Hanks, Christopher Walken and Martin Sheen. A critical and commercial smash which made over $350 million at the box office while being nominated for two Academy Awards, Catch Me If You Can retains a spot near the top of the con artist genre for a wide variety of reasons, with both DiCaprio’s performance and the affectionately antagonistic relationship between Frank Abagnale and FBI Agent Carl Hanratty receiving significant praise.
1. The Sting (1973)
Released in 1973 but set in 1936, The Sting remains one of cinema’s true classics and the only con film which can claim to have received 10 Academy Award nominations (of which it won seven, including Best Picture, Best Director and Best Original Screenplay). Directed by George Roy Hill and starring Paul Newman and Robert Redford as two of cinema’s most charismatic con men, The Sting sees the duo attempting to pull off a long and complicated con on a mob boss (as played by Robert Shaw). A wildly entertaining movie that mixes a heaping dose of old timey charm with the suave, collected cool of actors like Newman and Redford, The Sting is undoubtedly the greatest con movie ever made.