The Encyclopedia of Scams Cinematic Scams page features some of the greatest con artist films of all well as a few turkeys.

I have avoided listing films which main claim to the con artist world is a deceptive character based plot twist (E.g. Primal Fear, The Usual Suspects) or those who have a criminal character who is called a con artist without pulling any real cons. (e.g The Distinguished Gentleman, Bandits) or those with fictional or impractical scams (e.g. Ocean's Eleven, Wag The Dog)

$5 a day (2009)
Christopher Walken plays a small time con artist who hates spending money. He attempts to reconnect with his son as they drive cross country spending just $5 a day.
Our rating: unreviewed.

21 (2008)
A group of MIT students learn to count cards and try to win at Vegas. Based on the already exaggerated 'non-fiction' book Bringing Down The House, 21 is a copy of a copy of the truth. Criticized for straying too far from the true story and for replacing the almost entirely Asian characters with almost entirely white characters.
Our rating: 3.5 out of 5

Bedtime Story (1964)
The original Dirty Rotten Scoundrels starring Marlon Brando and David Niven. Features the Romance Scam with more focus on bedding women then making money from them. The moral of the story, that women and the men who marry them are both suckers , means that this film has not dated well.
Our rating 2.5 out of 5

The Black Swindler (2006)
Based on the popular Manga and Japanese TV show, The Black Swinder is a con man who, following the death of his family, seeks revenge on the swindling community by 'eating' other swindlers. Descends into melodrama at points but is still and enjoyable and original film.
Our rating: 4 out of 5

Believe (2007)
A little seen mockumentary about the world of multi-media marketing. I'm currently looking for people interested in helping promote the film through a very special business opportunity. Sit down and let me tell you all about it....
Our rating: unreviewed

Blue Streak (1999)
Martin Lawrence plays a jewel thief who impersonates a police officer to get to his stash. Enough said.
Our rating: 1 out of 5

Bluff aka Con Artists aka High Rollers (1976)
An Italian farce featuring plenty of double crossing, jail breaks and swindles.
Our rating: Unreviewed

Bluffmaster! (2005)
Like Ek Khiladi Ek Haseen, this Bollywood films openly steals from other, better films including Criminal, Nine Queens and Matchstick Men.
Our rating: Unreviewed

Boiler Room (2000)
The inner workings of boiler room investment scam. Boiler Room is to the stockmarket swindles of the early 21st century what Wall Street and Glen Garry Glen Ross were to the money hungry 80s. Trivia: The "Yellow Kid" Weil, who inspired The Sting, claimed to have invented the boiler room back in the early 1900s. Features the boiler room scam.
Our rating: 3.5 out of 5

The Brothers Bloom (2009)
This old fashioned caper about two con artist brothers is great fun. It also features the fresh idea of a con man wanting to go straight so he can live an 'unwritten life." Our rating: 5 out of 5 Capers

Catch Me If You Can (2002)
Based on the life of Frank Abagnale, one of the greatest paper hangers of all time. Also, the highest grossing con man moving ever! The film is remarkably close to the true story, only moving around a few events to help the narrative flow.
Our rating: 4.5 out of 5

The Cincinnati Kid (1965)
Steven McQueen is an up-and-coming poker player tries to prove himself in a high-stakes match against a long-time master of the game. As the stakes get higher, he finds himself mixed up with card cheats. The chances of the final two hands being dealt in one round are 332,220,508,619 to 1 and yet the film still feels gritty and real.
Our rating: 4 out of 5

Colour Me Kubrick (2005)
An English con man pretends to be Stanley Kubrick for both status and money. There is something tremendously sad about this dreary picture. John Malkovich is the star and provides the core of this one man band. Features the Impersonation scam.
Our rating: 4 out of 5

Confidence (2003)
Edward Burns plays a con man who cons the accountant of crime boss. He has to run a big store scam to get the money back. Rather than actually being a great con artist film, Confidence is pretending to be one. The characters drop words like 'shill' and 'mark' into their dialogue to remind you they are con artists.
Our rating: 2 out of 5

Conflict (1930)
A lumberjack and boxer is roped into a fixed boxing scam forcing him to choose between money and his friends. Features the fight store.
Our rating: 3 out of 5

Criminal (2003)
The American remake of Nine Queens minus the political upheaval and economic turmoil of the original. Features the Coin Collector Scam, Change Rising, Missing Change and Advance Fee Fraud.
Our rating: 4 out of 5

Diggstown (1992)
A con man bets a millionaire that a faded boxer can beat 24 boxers in 24 hours. This is very much a fight movie that retains elements of con artistry. In others, the ability to box does play a part in the success of the scam. Features the fight store.
Our rating 3 out of 5

Dirty Rotton Scoundrels (1988)
Steven Martin and Micheal Caine play con artists who compete to win the right to con in a small French town by seeing who can scam the most money out of a American tourist. A remake of 'Bedtime Story' that far surpasses the original. The final twist is great fun, even if you see it coming. Features the romance scam.
Our rating: 4.5 out of 5

Dr Mabuse, der Spieler (1922)
An evil mastermind hypnotises his victims into giving him their money. Features stockmarket swindles and psychics .
Our Rating: 4 out of 5

Elmer Gantry (1960)
Elmer Gantry is a con man who teams up with a female preacher to sell religion to the masses.
Our rating: unreviewed

Flim Flam Man (1967)
A master con man takes a young army deserter under his wing and teaches him the tricks of the trade. The film presents an accurate depiction of depression era con artists despite being set in the 1960s. Also, a man gets hit on the head with a giant sausage. Includes punchboard scams, three card monte and the pigeon drop.
Our rating: 4 out of 5

F is for Fake (1974)
A semi fictional documentary about forger Elmyr De Hoyr that also features interviews with Clifford Irving, the writer who forged the Howard Hughes autobiography. The final film of Orsan Wells.
Our rating: 5 out of 5 Picassos

Freelance (1971)
Ian McShance, of Deadwood fame, plays a small time con artist who witnesses a mugging and ends up with a hitman on his tail. This is classic 70's Brit noir in the same vein as Get Carter and the other Micheal Caine crime films of the same era.
Our rating: unreviewed

The Little Golden Calf (1968)
Ostap Bender, a con man in Soviet Russian, attempts to extort 1 million from an underground millionaire in this classic Russian comedy. The film is based on the Petrov novel of the same name. While not available in English on DVD, this film is available on youtube with English subtitles.
Our rating: unreviewed

Grapes (2008)
A Czech con artist and his girlfriend spend their days renting apartments and then re-renting it to several people, collecting rent and bond from all and vanishing before anyone moves in. With the police hot on their tails, the con artist decides to hide out in the family vineyard where he discovers their are more important things than swindling.
Our rating: unreviewed

The Great Imposter (1961)
Tony Curtis stars as Fred Demara, a real life imposter who pretended to be a jail warden, a doctor, a priest, a teacher and many more in his long career as an imposter. The film manages to transform the portly and argumentative Demara in a suave precursor to Catch Me If You Can. Demara was supposedly the inspiration for the 1990's TV series, The Pretender.
Our rating: 3 out of 5

The Grifters (1989)
Insurance fraud, dice games, race course, pump and dump, bar bets, cackle bladder. Bonus points for not falling into the usual "short con-short con- long con - twist" structure of most con artist films the period. Loses points by having the mentor doing a bad card trick and calling it cheating.
Our rating: 3 out of 5

Heartbreakers (2001)
A mother and daughter con artist team scam lonely single men. This broad comedy aims to be an all female version of Dirty Rotten Scoundrels but doesn't quite succeed. Features the romance scam and the Free Lunch.
Our rating: 3 out of 5

Holy Rollers (2011)
The true story of a group card-counters who also happen to devout christians. Fascinating documentary that explores the ethics of card counting and casino culture: Our rating: 4 out of 5.

House Of Games (1987)
A pyschologist helps a con artist discover the 'tells' in rival poker players. Features Card Cheating.
Our rating: 5 out of 5

Leap of Faith (1992)
Steve Martin plays a fake faith healer who travels the countryside, convincing people he can heal and tell their fortunes. Features scams used by Swamis.
Our rating: 3.5 out of 5.

Lock, Stock and Two Smoking Barrels (1998)
Four friends get drawn in the crime underworld when their leader loses 250,000 pounds in a game of cards. Features Card Cheating and the sex toy scam.
Our rating: 4 out of 5

The Hoax (2007)
The true story of Clifford Irving, the man who tried to sell the reclusive Howard Hugh's autobiography. Despite him never having written one.
Our rating: 2 out of 5.

Honky Tonk (1941)
Clark Gable plays a con man who reveals the three card monte to save his skin.
Our rating: Unreviewed

It's The Old Army Game (1923)
WC Fields plays a drugstore owner who unwittingly becomes a part of a bogus land deal scam. The poster for the film features WC Fields throwing monte.
Our rating: Unreviewed.

Kaledidoscope (1966)
Warren Beatty plays a card cheat who breaks into a card factory and marks the plates used to print the cards allowing him to win any game, anytime.
Our rating: Unreviewed

The Lady Eve (1941)
Like Bedtime Story, Dirty Rotton Scoundrels and Heartbreakers, The Lady Eve combines the con artist genre with the romantic comedy. Barbara Stanwyck plays a con woman who falls in love with her mark played by Henry Fonda. With plenty of back stabbing and twists this is golden era comedy.
Our rating: 4 out of 5

Les plus belles escroqueries du monde (1964)
Four directors each tell a tale of swindlers in this French anthology film. Imagine the Twilight Zone movie but with con artists instead of supernatural stories and french new wave cinema instead of 80s B-grade blockbuster.
Our rating: unreviewed

Ek Khiladi Ek Haseena (2006)
A low budget Bollywood film jammed full of fairly average musical numbers and product placements. The film steals heavily from both House of Games, Confidence and Matchstick Men. .
Our rating: 2 out of 5

The Man With The Golden Arm (1955)
Frank Sinatra plays a heroin addict who tries to go straight and become a drummer. However, his skills as a card cheat lead his formal associates to try and drag him back in. Features Card Cheating.
Our rating: 4 out of 5.

Matchstick Men (2003)
A daughter meets her con artist father for the first time and is drawn into his world. Features the Lottery Ticket Scam, Bank Examiner and Advance Fee Fraud.
Our rating: 4 out of 5

Maverick (1994)
A card cheat crosses paths and swords with a con woman and a law enforcement officer. Features Card Cheating and Police Impersonators.
Our rating: 5 out of 5 (don't ask me why, I just love this movie)

Mississippi Gambler (1953)
A professional gambler takes on a swindler at three card monte.
Our rating: unreviewed

Mo Money (1992)
Damon Waynes plays a con man who 'goes straight' to impress a girl but ends up in a stolen credit card scam.
Our rating: 2.5 out of 5

The Music Man (1962)
A travelling con man tries to swindle the people of a small Iowa town into funding a non-existent marching band.
Our rating: unreviewed

The Music Man (2003)
A 2003 remake of the 1962 film.
Our rating: 1.5 out of 5

My Chauffeur (1986)
Magicians Penn and Teller play con man and victim in this short comedy about three card monte.
Our rating: Unreviewed

Nightmare Ally (1947)
Tyrone Powers plays a con man who steals the secrets of a phony psychic's act and becomes a star with them.
Our rating: 3.5 out of 5

Nine Queens (2000)
A master con man takes a young man under his wing to teach him the tricks of the trade against the backdrop of Argentina's economic struggles. Features the Coin Collector Scam, Change Rising, Missing Change and Advance Fee.
Our rating: 5 out of 5

Ocean's Thirteen (2007)
Danny Ocean and his team finally pull some real scams as they rigged dice games, card games and poker machines in a casino.
Our rating: 2.5 out of 5.

The Old Army Game (1943)
Cartoon short in which Donald Duck goes AWOL from the army. He hides one of three three boxes from his commanding officer in a parody of the shell game. The Old Army Game is another name for the Shell Game.
Our rating: 3 out of 5

Paper Moon (1973)
A con man and his daughter travel through depression era America. Features the Delivery Man, Change Rising and Missing Change.
Our rating: 5 out of 5

The Past Is A Foreign Land (2009)
A law student gets mixed up with a card cheat in this darker Italian thriller. The card cheating 'skills' are more akin to magic tricks but the psychology of the cheat and the psychopathic desire for 'control' make this film a cut above the rest. You may also enjoy the book of the same name.
Our Rating: 4 out of 5

The Prime Gig (2000)
Vince Vaughn plays a con artist who specializes in boiler room telemarketing. Recruited into a team to make a fortune in a gold mining scam.
Our rating: 3,5 out of 5

Princess Caraboo (1994)
Phoebe Cates (from Gremlins, remember Gremlins? Great film.Scared the hell out of me) plays the titular role as a non English speaking princess from a far away land who ingratiates herself in at 19th Century Bristol family. It's inclusion on this list suggests she is not all she appears. Based on a true story.
Our rating: unreviewed

The Producers (1968)
A theatre producer and accountant try to swindle investors out of money by producing a flop. The resulting play 'Springtime For Hitler" is a smash hit.
Our rating: 3.5 out of 5

The Producers (2007)
A theatre producer and accountant try to swindle investors out of money by producing a flop. This version is a musical based on a movie about a musical.
Our rating: 1.5 out of 5

The Rainmaker (1956)
A charming con man convinces the residents of a small town he can make it rain...for $100. Features advance fee fraud.
Our rating: unreviewed

Rogue Traders (1999)
A fictional retelling of the story of fraudulent trading of Nick Leeson, the man who destroyed Barings bank in 1995. Our rating: 3 out of 5

Rounders (1998)
A poker player and his friend, a poker cheat, try to pay off a big debt by a mixture of good poker and good cheating. Perhaps the most accurate depiction of poker and cheating on the big screen, Rounders is responsible for inspiring the breed of poker players and, in turn, the rise in popularity of Texas Hold'em. Features Card Cheating.
Our rating: 4 out of 5

Scam (1989)
A female con-artist who seduces wealthy men and then robs them for her violent boyfriend is being herself being watched by another con artist who has plans for her talents.
Our rating: unreviewed

Skin Game (1971)
Two con men play the roles of slave owner and slave. The slave is 'sold' only to escape and return to the 'slave owner' where the split the money. Features the coin collector scam.
Our rating: unreviewed

Shade (2003)
A group of card cheats get together to take down the best card cheat in the world. This is fun film but feels very much like a magician's view of card cheats. Most of the characters are named after famous card magicians and, at one point, a player magically produces four jacks at the card table in the middle of a game and DOESN'T get the shit kicked out of him. Features card cheating, big store, crossed deck and the Old Fiddle.
Our rating: 3 out of 5

Shell Game (1975)
The pilot for a TV show that was never picked up, Shell Game is classic con artist story filled with long cons, gold mine swindles and the shell game of the title. A con-artist, recently released from prison tries to reclaim money stolen from a charity. Despite it being a low budget, straight to video flop, Shell Game is a cut above the average scam film of the time with a great horse racing scam and an excellent take of a gold mining scam.
Our rating:3.5 out of 5

Shooting Fish (1997)
Two con artists find their unethical lives are thrown in disarray by a beautiful woman. It attempts to be a post-trainspotting brit pop independent film but ends up feeling more like a fluffy Ealing studios film from the 1950s. Features Coin Collector Scam, Light bulb Salesman Counterfeit Money .
Our rating: 3 out of 5

Six Degrees of Separation (1994)
Will Smith plays a con artist who impersonates Sidney Poiter's son in order to gain access to a rich New York family. Based on the play The Kadinski Has Two Faces. My high school staged a production of the play in which 'Sidney Poiter's son' was played by a pale red head. Didn't quite work.
Our rating 4 out of 5

Sidekicks (1976)
A remake of Skin Game designed as a pilot for a TV series that was never produced.
Our rating: 2 out of 5

Simpatico (1999)
Three con artists make a bundle by swapping top race horses for bad ones, cleaning up with big bets on the long odds. 20 years later, their past catches up with them.
Our rating: 2 out 5.

Smart Money (1929)
Edward G Robinson and James Cagney share the screen for the first and only time in this story of a small town barber who is also the 'luckiest man alive'. Keen to turn his skill at gambling into a fortune, he takes his 10,000 dollars of his friend's money into a poker game, unaware that the game is crooked.
Our rating: 4 out of 5.

Spanish Prisoner (1997)
David Mamet's study of a victim of the classic Advance Fee Fraud. While the premise of the Spanish Prisoner makes up the lion share of the plot, the execution is a little unbelievable.
Our rating: 3 out of 5

The Sting (1973)
A con man seeks revenge for the death of his friend by teaming up with a master scammer in a classic long con. The Sting is the standard against which all other con artists are judged. The story is based on the life of The Yellow Kid Weil and the book, The Big Con by David Maurer, who sued the filmmakers. Features the Pigeon Drop, Card Cheating and the Big Store.
Our rating: 5 out of 5

The Sting 2 (1983)
The sequel to the original film with new actors in the lead roles. The film makers have create a messy scam full of holes set in the world of boxing.
Our rating: 0.5 out of 5.

The Swindler (1997)
A pair of French swindlers, Betty and Victor, cross the country in an RV in this Hitchcock style comedy.
Our rating: unreviewed

Swindled aka Incaustos (2003)
In a flashback, a young Spanish con man, tells how he got to the edge of a big score. Including his aging mentor, his partner and a beautiful woman, this film feels like a second rate Nine Queens, but this Spanish scam film ticks all the boxes with a fun twist and plenty of short cons.
Our rating: 4 out of 5.

The Super (1991)
An average film about a landlord forced to live in one of his slums. Features the best depiction of three card monte ever featured in a film
Our rating: 2.5 out of 5 for the film but 5 out of 5 for the depiction of the monte

Three Card Monte (1976)
A two bit hustler working the streets in Canada hooks up with a young boy and teaches him everything he knows. Features a note perfect depiction of three card monte how it's really played, crooked dice and various short cons.
Our rating: 3.5 out of 5.

The Tichborne Claimant (1998)
The true story of the wagga butcher who pretended to be the missing son of a wealthy french noblewoman.
Our rating: 3.5 out of 5

Traveller (1997)
Bill Paxton and Mark Wahlberg play nomadic con artists in South Carolina
Our rating: unreviewed

White Men Can't Jump (1993)
Woody Harrelson and Wesly Snipes play a pair of con artists who hustle money on the LA street courts. Features a version of the crossed deck with basketball! Our rating 3 out of 5

Honourable Mentions

Films that might not, technically, be about swindlers, cheat and con man but that certainly fit within the con artist's world.

A Big Hand For The Little Lady (1966)
A gambling movie about a small family in the old west who get sucked into a high stakes poker game. The film moves along at a cracking pace despite most of action occurring at the poker table. Watch closely and you'll notice that no one actually cheats.
Features card playing and a long con.
Our rating: 4 out of 5

Colour of Money (1986)
While this sequel to The Hustler doesn't live up to the original, it's dark look at the seedy side of pool halls is still top cinema.
Our rating: 4 out of 5.

Duplicity (2009)
Julia Roberts and Clive Owen star as ex-spies and lovers who are hired by rival companies to spy on each other. The films many twists and turns are original and unexpected and the concept of basing a con artist film in the corporate world is original. However, Roberts and Owen have no chemistry and they all but kill the film.
Our rating: 2.5 out 5

Harry In Your Pocket (1973)
A highly accurate depiction of the world of the pickpocket. The Sting of pickpocket films
Our rating: 4 out of 5

Heist (2003)
While this David Mamet film revolves around the theft of gold from an airport, the various twists and turns conjour up images of the Spanish Prisoner and House of Games.
Our rating: 4 out of 5

Ocean's 11 (2001)
George Clooney's heist film, like Heist, plays out more like a long con that a theft. Great fun.
Our rating: 4 out of 5

The Hustler (1961)
A young, up and coming hustler plays "Minnesota Fats" in a marathon pool game.
Our rating: 4.5 out of 5

The Pickpocket (1957)
Robert Bresson's classic film about morality and identity. A petty thief slowly becomes a master pickpocket despite his friends attempts to help him out.
Our rating: 4.5 out of 5.

Rainman (1988)
A car salesman and his autistic but mathematically genius brother travel cross country. Along the way, they hustle a casino by using Raymond's math skills to count cards. The film implies that Raymond is a genius because he can count six decks. This is untrue.
Our rating: 4 out of 5

The Talented Mr Ripley (2001)
Matt Damon plays an amoral con artist who pretends to be a school friend of a rich man's son.
Our rating: 4 out of 5