Somehow con artists are some of the most endearing characters in movies, despite their complicated relationship with the law. Here are some movie con artists who just keep stealing our hearts.
Addie Loggins and Moses Pray in Paper Moon (1973)
If you’re setting out to tell a sympathetic story about con artists, set it during the Great Depression so the audience understands they don’t have much choice but to pull off grubby cons. And make one of them an adorable kid.
Peter Bogdanovich’s Paper Moon those narrative tricks and many more to make you fall in love with Moses Pray and Addie Loggins, who might — just might — be father and daughter, just like the actors who play them (Tatum and Ryan O’Neal, pictured in character).
O’Neal won Best Supporting Actress for the role, making her, at 10, the youngest Oscar winner.
Louis Winthorpe III and Billy Ray Valentine in Trading Places (1983)
After a mean-spirited bet causes them to trade lives, Dan Aykroyd’s yuppie-turned-homeless man Louis and Eddie Murphy’s homeless-man-turned-yuppie Billy Ray team up to take down Randolph and Mortimer Duke (Ralph Bellamy and Don Ameche), the bored rich brothers who played them like puppets.
Louis learns street smarts and Billy Ray learns market manipulation, making them both adept con man at opposite sides of the social hierarchy. Trading Places takes the view that luck matters every bit as much in life as hard work — unless you find a way to manipulate the odds.
It’s impossible not to root for Louis and Billy Ray, especially once they enlist the stagecraft of Jamie Lee Curtis’ Ophelia, a sex worker with a heart of gold.
‘Fast Eddie Felson’ in The Color of Money (1986)
This sequel to 1961’s The Hustler finds Paul Newman reprising his role as “Fast Eddie” Felson, for which he won an Oscar. In the original film, he’s a hotshot humbled by Jackie Gleason’s Minnesota Fats. This time, he’s the old hand, and Tom Cruise plays Vincent, the young hotshot who thinks he knows everything.
One of the joys of The Color of Money is how much fun it has with the fact that being good at pool hustling isn’t the same as just being good at pool: Felson has to constantly calculate how good he is compared to his opponent, and mislead his adversary accordingly.
Lawrence Jamieson and Freddy Benson in Dirty Rotten Scoundrels (1988)
Steve Martin and Michael Caine are irresistible as a pair of rivals-turned-partners in Frank Oz’s endlessly inventive farce about womanizing con artists in the French Riviera. Caine’s Lawrence Jamieson is sophisticated and impressive, and Martin’s Freddy Benson cheap and crass.
When they try to team up to bilk Janet Colgate ( an excellent Glenne Headly), the naïve “United States Soap Queen” out of her millions, things don’t break as anyone expects. You’ll love this movie or my name isn’t Dr. Dr. Emil Schaffhausen.
This is a remake of 1964’s Bedtime Story, starring Marlon Brando, David Niven and Shirley Jones.
Henry Gondorff and Johnny Hooker in The Sting (1973)
Everything about. George Roy Hill’s Depression-era caper The Sting is a joy — the Scott Joplin music, the re-pairing of Butch Cassidy and the Sundance Kid stars Robert Redford and Paul Newman, the pacing — but what’s most fun is trying to figure out how the scams work.
The film’s many complicated schemes culminate in a brilliant reality-bending betting parlor setup concocted by Newman’s Henry and Redford’s Johnny, two of the most influential of all movie con artists.
The film deservedly won a slew of Oscars, including for Best Picture, Best Director and Best Original Screenplay.
Frank Abagnale Jr. in Catch Me If You Can (2002)
It’s been said that charm is a quality that makes you want to say yes before you even know the question, and Leonardo DiCaprio overflows with it onscreen. He’s extremely adept at playing endearing young con artists. Somehow the people around them, especially women, always want them with their schemes instead of calling the cops.
One of the best examples is in his portrayal of Frank Abagnale Jr., the real-life young con artist turned security consultant who stars in Steven Spielberg’s kinetic and fun Catch Me If You Can.
Its stunning lineup of great actors, in roles big and small, also includes Tom Hanks, as a fictionalized version of the fed who caught the real Abagnale, Christopher Walken, and Amy Adams, who appears later in this gallery.
Jordan Belfort in The Wolf of Wall Street (2012)
Leonardo DiCaprio delivered a darker take on con artists with The Wolf of Wall Street, another based-on-a-true-story tale. It’s the second Martin Scorsese film on this list, after The Color of Money.
DiCaprio and Scorsese’s take on real-life trader Jordan Belfort is that he seems more driven by greed than fun. As a result, he always seems a little secretly miserable, even in the midst of his most head-spinning success. But DiCaprio is so charismatic that you somehow sympathize with Belfort, even knowing that he’s the cause of all his own problems.
The real Belfort pleaded guilty in a complex stock manipulation scheme and served 22 months in prison. He’s pretty seductive himself, at least as a writer — his 2007 book The Wolf of Wall Street, the inspiration for the movie, is an addictive page turner.
Sydney Prosser in American Hustle (2013)
Amy Adams in American Hustle, distributed by Sony Pictures Releasing.
Amy Adams’ Sydney Prosser — who also goes by the “Lady Edith Greensly” — is the more lovable, seductive half of a con artist partnership with Christian Bale’s Irving Rosenfeld.
When FBI agent Richie DiMaso (Bradley Cooper) catches them in a loan scheme, the FBI enlists them in a sting operation to snare the mayor of Camden, New Jersey, Carmine Polito (Jeremy Renner).
You can get caught up in the complicated criminal machinations of American Hustle, or just enjoy the lavish late ’70s-early ’80s vibes and incredible performances, as well as the glitzy wardrobes of Prosser and Irving’s wife, Rosalyn (Jennifer Lawrence.) The movie looks dazzling, and Prosser is so charming that you find yourself rooting for her even when you shouldn’t. And it’s even based on a true story.
Like This List of Movie Con Artists?
You can learn about the consequences of conning people with this list of great prison movies.
Main image: American Hustle.
Editor’s Note: Corrects lede, typos and formatting.
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