Top 10 Con Movies of All Time

Accounts of con artists have been around since man learnt to pick up a ballpoint pen.

In recent history, there have been numerous con artists who have really stood out for either the wealth they amassed or the ease with which they tricked their ‘marks’. The tales of hoodwinking are thrilling because they almost always feature people smart and cunning enough to steal from the rich and line their own pockets using complicated trickery.

Some of the best movies ever made are about con men and their fascinating schemes, ranging from exciting heist adventures to following a scammer as he or she darts from town to town, scamming any and all in sight.

This ‘Top 10 List of Best Con Movies of All Time’ includes movies from all different time periods, from as far back as 1961 to modern day scammers. (Please do forgive us if we omit a few good titles).

#10: The Hustler (1961) (Starring Paul Newman, Jackie Gleason, Piper Laurie, George C. Scott)

The Hustler
The universal “Oh sh*t” face when you suddenly realise you’ve been snookered.

‘The Hustler’ is a 1961 American drama film that is based on the 1959 novel by American writer Walter Tevis. It tells the story of a young pool hustler, Edward “Fast Eddie” Felson (Paul Newman), and his desire to break into the “major league” of professional hustling and high-stakes wagering. He pits his raw talent and ambition against the best player in the country and challenges the legendary “Minnesota Fats” (Jackie Gleason).

After initially losing to Fats and getting involved with an unscrupulous manager named Bert Gordon (George C. Scott), Eddie returns to beat Fats in a single high-stakes match; but only after paying a terrible personal price. Afters Fats devastating defeat, he is forced to quit from pool. Meanwhile, Bert, Eddie’s immoral manager, demands a share of Eddie’s winnings but Eddie sternly refuses quoting “He’d have to kill him first”; Bert backs down but warns Eddie to never walk into a big-time pool hall ever again.

The film was a major critical and commercial success, gaining a reputation as a modern classic with its exploration of winning, losing, and its characters. The Hustler was nominated for multiple Academy Awards, 9 to be exact, but won only 2; for Best Art Direction-Set Decoration and Best Cinematography.

*On a side note, The Hustler is credited with sparking a resurgence in the popularity of pool in the United States, which had been on the decline for decades.

#9: Ocean’s Eleven (2001) (Starring Brad Pitt, Matt Damon, Julia Roberts, George Clooney, Andy Garcia)

Ocean's Eleven
I still prefer the original 1960 poster though. (See below for original poster)
Ocean's Eleven #2
The original ‘Ocean’s 11′ Poster: It oozes nothing but pure, unadulterated class. They sure don’t make them like they used to.

‘Ocean’s Eleven’ is a 2001 American comedy-crime film, which is a remake of the 1960 Rat Pack film of the same name, which follows the main protagonist con artist Danny Ocean who has recently been paroled from prison in New Jersey. And he wants to do what any con artist would do upon being released from a federal penitentiary: score the biggest heist in history.

His plan is to stage heists of three major Las Vegas casinos, The Bellagio, the Mirage and the MGM Grand during a popular boxing event and secretly get in and out with $150 million; all casinos, by the way, are owned by ruthless entrepreneur Terry Benedict (With a name like that, you’d expect him to be an assh*le to some capacity). Ocean rounds up a gang of 11 associates, who comprise of a thief out of retirement, a pickpocket, a card dealer, a surveillance man, a Chinese acrobat, an explosives expert, two frontmen, and a bitter casino mogul.

Oh, and one other thing, there are three rules to be followed: First:no blood. Second: Rob only who deserves it. Third: Do it as if you have nothing to lose.

The film was a huge success both at the box office and with most critics, with it earning $450 million worldwide; making it the fifth highest-grossing film of 2001. This led to the inevitable creation of two more sequels, ‘Ocean’s Twelve’ in 2004 and ‘Ocean’s Thirteen’ in 2007; resulting in the term ‘Ocean’s Trilogy’.

(Because nothing says ‘beating a dead horse’ like producing 3 almost identical films that gravitate around the same central idea; except that they add one more character to the crew with each film to make it a tad more interesting).

#8: House of Games (1987) (Starring Lindsay Crouse, Joe Mantegna)

House of Games
“A 1987 Guide How-To-Guide On: Flirting with the opposite sex.”

‘House of Games’ is one of David Mamet’s best twist/con game films that involves a famous psychiatrist, Dr. Margaret Ford (Lindsay Crouse), who decides to try to help one of her compulsive gambler patients get out of, none other than, a $25,000 gambling debt; the patient, of course, does not have the money and will soon have his life prematurely ended if he does not cough it up.

Dr. Ford visits the bar where Mike (Joe Mantegna), to whom the debt is owed, runs poker games. Sleazy and alluring Mike, who is the leader of a group of con artists, convinces the respected psychiatrist to help him with his grifts: her assignment is to look for “tells”, or give-away body language. What seems easy to her becomes much more complex as she is led by smooth-talking grafter Mike into the shadowy but compelling world of stings, scams, and con men; before she knows it, she soon becomes hooked on the adrenaline rush of their scams.

House of Games netted an outstanding sum of $2.5 million upon its worldwide release and holds a staggering 96% ‘Fresh Rating’ on film review and news site Rotten Tomatoes; one of only a few classics to be awarded such an exceptional grade.

 #7: Dirty Rotten Scoundrels (1988) (Starring Steve Martin, Michael Caine, Glenne Headly, Anton Rodgers, Barbara Harris)

Inspector Clouseau and Alfred Pennyworth before the economy tanked, circa. 1988.
Inspector Clouseau and Alfred Pennyworth before the economy tanked, circa 1988.

‘Dirty Rotten Scoundrels’ is a 1988 American comedy film that centres around the story of two unique con men competing to swindle an American heiress out of $50,000; what makes this film a classic, and what also got it on this list, is that the two con artists are working against each other, not in tandem (If you hadn’t noticed, almost every con artist is the friendliest, most cooperative bunch going).

One the one hand, Lawrence Jamieson (Michael Caine) is the literal embodiment of a suave con man, who believes in conning corrupt, rich people out of their money so he can spend it on culture and a lavish lifestyle; on himself. On the other hand, Freddy Benson (Steve Martin) plays Jamieson’s laddish, arrogant American rival, who believes in conning just about anyone in order to get a free meal. The swindling duo end up in the same Mediterranean town in the French Riviera and agree to work together bamboozling the rich.

Although Dirty Rotten Scoundrels features a seemingly never-ending flurry of cons on top of cons, its juicy centre is the interplay between Benson and Jamieson. Seeing Caine and Martin go toe-to-toe and play off each other is a real comedic treat, and makes the film well worth it.

Dirty Rotten Scoundrels netted an impressive $42 million at the box office in the United States and went on to be ranked number #85 on ‘Bravo’s #100 Funniest Movies’.

#6: The Grifters (1990) (Starring John Cusack, Anjelica Huston, Annette Bening)

The Grifters
What I presume every porno cover looked like back in the day.

‘The Grifters’, directed by Stephen Frears and produced by Martin Scorsese, is an intricately plotted and gritty 1990 neo-noir film set in Los Angeles. Small-time con man Roy Dillion (John Cusack) is visited by his distant, and somewhat estranged, mother Lilly Dillion (Angelica Huston); who is also coincidentally a veteran con artist.  Lilly begins to rethink her life and her relationship with her son after Roy suffers a near-fatal injury when hit with the blunt end of a baseball bat; a result of a scam gone wrong.

Not long after, Roy’s girlfriend Myra Langtry (Annette Bening), whom Lilly takes an instant disliking to, enters the picture; she too, unsurprisingly, is also a con artist of sorts. Roy is then confronted with the decision of either listening to his mother’s plea of giving up grifting for good or giving in to the allure of continuing his deceitful ways, with slutty girlfriend Myra, in hopes of bigger paydays. Roy is then left torn between his loyalties whilst both deviously intelligent women try to work their own angles on him and a grift, which eventually leads to soon falling apart for the three con artists; resulting in a bloody climax.

Even though The Grifters had a brief Academy Award-qualifying run and received mostly positive reviews from critics, it only earned a meagre $125,195 on its opening weekend; ultimately, the film was successful in its limited run.

#5: Paper Moon (1973) (Starring Ryan O’Neal, Tatum O’Neal, Randy Quaid, Madeline Kahn)

Back when a smoking child sitting on a moon was considered acceptable to many, and an obligatory rite of passage for some.
Back when a smoking child sitting on a moon was considered acceptable to many, and an obligatory rite of passage for some.

‘Paper Moon’ is a 1973 American crime-drama film, which is shot in black-and-white, and is set in Kansas and Missouri throughout the depression-era of the Midwestern region of the United States.

Mose (Ryan O’Neal) and young, charming Addie Loggins (Tatum O’Neal) shine in this story of an unlikely father-daughter partnership conning their way around America during the Great Depression. The two travel from town to town delivering unordered Bibles and charging exorbitant prices to recently widowed women whom Mose identifies through the obituary columns of local papers.

Soon, Addie and Mose become a team, traveling from town to town, making money in every dishonest way imaginable, whilst looking for the ultimate score. The colourful characters they meet along the way make the film all the more interesting; such as exotic dancer Trixie Delight (Madeline Kahn) who becomes an integral part of the story.

It stars the real-life father and daughter pairing of Ryan and Tatum O’Neal, as Moze and Addie respectively, and Madeline Kahn who gave what many believe to be the best of her many great supporting roles. The film was nominated for Best Sound, Best Adapted Screenplay at the Academy Awards in 1973 (Which, by the way, was a HUGE deal back when people didn’t actually know what it was).

4: Matchstick Men (2003) (Starring Nicolas Cage, Sam Rockwell, Alison Lohman, Bruce McGill)

Ghost Rider’s former career.
Ghost Rider’s former career, probably.

‘Matchstick Men’ is a 2003 American comedy drama film directed by Ridley Scott [Alien (1979), Thelma & Louise (1991), Gladiator (2000) Prometheus (2012)]. Based on Eric Garcia’s 2002 novel of the same name, the film stars one of Nicolas Cage’s best performances as a heavily medicated con artist with obsessive compulsive disorder (OCD); whose life is further complicated by the arrival of a daughter he’s never known. However, despite what many believe to be a debilitating condition, it turns out to be the very thing that makes him a successful con man; and one that’s very entertaining to watch.

Over the course of the film, Roy Waller (Nicholas Cage) slowly assimilates his ‘daughter’ Angela into his ‘profession’ and introduces her to his partner Frank Mercer (Sam Rockwell). While Mercer is the flashier con man of the two, Waller is the “brains,” which makes them a perfect team; however Cage’s portrayal of an exceedingly manic Waller is what makes this film so entertaining.

The film received mostly positive reviews from critics, with some calling it the finest con film since ‘The Sting’ (Which is also on this list), and earned a respectable $65.5 million worldwide; after grossing an underwhelming $36.9 million domestically. Unfortunately, the film was virtually ignored during the awards season, receiving no Oscar nominations despite positive reviews. However, the film found better success on home video and has since garnered a cult following.

#3: The Usual Suspects (1995) (Starring Stephen Baldwin, Gabriel Byrne, Kevin Spacey, Benicio del Toro, Kevin Pollak)

Possibly one of the best movie posters ever released
Many say that this is the final resting place of Bruce Willis’s hair.

‘The Usual Suspects’ is a 1995 German-American neo-noir crime film that follows the interrogation of Roger “Verbal” Kint. He is a small-time con man who is one of only two survivors of a massacre and a deadly fire on a ship docked at the Port of Los Angeles, who uses flashbacks and narration to tell the increasingly complex story.

We don’t want to give away too much detail in this review as The Usual Suspects is remembered for one of the most definitive and popular plot twists in all of cinematic history. All we can say is that this brilliant flick gave birth to the mysterious pop culture character ‘Keyser Söze’ and ends with the most poignant quote quite possibly to exist:

“The greatest trick the devil ever pulled was convincing the world he didn’t exist.”

Before being initially released in a few theatres, it was shown at the 1995 Cannes Film Festival. It received favourable reviews, and was eventually given a wider release after the film was given an exclusive run in Los Angeles and New York City; where it eventually grossed $23.3 million.

#2: Catch Me If You Can (2002) (Starring Leonardo DiCaprio, Tom Hanks, Christopher Walken, Martin Sheen, Nathalie Baye)

Probably one of the most accurate film explanations a poster could ever give you.
Probably one of the most accurate film explanations a poster could ever give you.

‘Catch Me If You Can’ is a 2002 American biographical crime drama film based on the real life of Frank Abagnale (Leonardo DiCaprio), who starts out as an idyllic teenager wanting nothing more than to see his parents happy. However, as things start to unravel at home, Abagnale turns to small (This term is used quite loosely) cons as a form of escape.

Those ‘small’ cons soon turn into elaborate second lives and before long Abagnale is on the FBI’s most wanted list. A cat-and-mouse game ensues and in spite of having Carl Hanratty (Tom Hanks), an FBI bank fraud agent, hot on his heels, he successfully performs cons worth millions of dollars by posing as a Pan American World Airways pilot, a Georgia doctor, and a Louisiana parish prosecutor; all before his 19th birthday.

Even though Frank’s primary crime was check fraud, he became notoriously skillful to the point that the FBI eventually turned to him for help in catching other check forgers. (I guess it’s true what they say “To catch a criminal, you must hire one that has worn more disguises than an exiled Communist fugitive”; or something along those lines). Since becoming a ‘consultant’ with the FBI, Frank has caught some of the world’s most elusive money forgers and earns millions of dollars each year because of his incredible work creating unforgeable checks

The film was a critical success, both financially and with viewers, earning $30 million during its opening weekend, with even the real Abagnale reacting positively to it. Granted, not all of the events in the film are true to life, but don’t allow that to undercut the astonishing feats the real Frank Abagnale Jr. pulled off.

#1: The Sting (1978)(Starring Robert Redford, Paul Newman, Robert Shaw)

“…and they I said to her ‘You’re lucky it was only herpes you wonky eyed broad’!”
“…and they I said to her ‘You’re lucky it was only herpes you wonky eyed broad’!”

‘The Sting’ is a 1973 American caper film set in September 1936 at the height of the Great Depression, and involves a complicated plot of two professional grifters who set out to con a mob boss. It has nearly all of the elements featured in a great con film, from the mismatched pairs to the long drawn con, and even the whole ‘last-second double con-con’;  and it all worked together beautifully (Like how dictatorships and mass murder go hand-in-hand so well).

The story was inspired by real-life cons perpetrated by brothers Fred and Charley Gondorff, which was documented by David Maurer in his book ‘The Big Con: The Story of the Confidence Man’. Honestly, The Sting wouldn’t be what it is without the characters of Henry Gondorff and Johnny Hooker who were excellently portrayed by Paul Newman and Robert Redford respectively. With the supporting actors, costumes, music, sets, and writing, it is a joy every time you watch it; even if you know the twist at the end!

The Sting was hugely successful at the 46th Academy Awards, which was presented in April of 1972, where it not only raked in a jaw-dropping $160 million (Which was a butt-load of money back in 1973-1974), it was also nominated for a whopping 10 Oscars; with it winning seven, including Best Picture, Best Director, and Best Original Screenplay.

[Written and Contributed by KieranHoggs]

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Writers Note:

In conclusion, any great con man film requires several things: an airtight con, an intriguing “mark” or foil, and a ton of misdirection both for the characters in the film and the audience. But most importantly, every great con man movie needs a great con man – someone who is charming, clever, cunning, and occasionally ruthless. They are typically good at heart and universal themes like trust, family, friendships and loyalty gravitate around the protagonist(s) like flies to poo, at least in the movies that is; however, their goals are never noble.

And make no mistake – con men are not mere thieves.

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