There is possibly no more enjoyable archetype in crime film than the con artist. Probably because it’s a fascinating profession. The con artist isn’t exactly a thief… he (or she) is more manipulative than that. A thief takes your money, but a con artist convinces you to give them your money. And that’s a big difference.
Here at CrimeReads, we often discuss the legendary pros of the great movie cons, and today, finally, we’re bringing that discussion to the site.
What are the rules? Simple. To be on this list, a character has to be more of a swindler than an actual thief. We’re talking confidence men, frauds, tricksters, charlatans, impostors, swindlers, shady real estate salesmen, pool hustlers, card sharks, and all other purveyors of flimflam.
Con movies also often feature excellent teamwork, so we’re keeping those teams together on our lists.
Without further ado, let’s deal you in.
80.
John Vogel, Flag Day
Sean Penn directs himself and his daughter Dylan in this movie about a dad who becomes a con artist to provide for his daughter. Sean Penn clearly loves his daughter a lot and I hope they enjoyed making it together. That’s all I’m saying.
79.
Josephine Chesterfield and Penny Rust, The Hustle
I love Anne Hathaway and I want nothing more than for her to make a fantastic buddy comedy with Rebel Wilson about two hilarious con artists. Sadly, the two characters both of them are asked to play are appallingly one-note. A pity, considering their scheme is supposed to yield them millions of notes.
78.
Benjamin Jones, The Catch
I’m tired, you’re tired, but at least you didn’t have to prep for this list by watching The Catch, ABC’s low-rent Out of Sight remake about a lady PI and fraud-exposer who falls for a con man.
77.
Cat Chambers, Reef Break
Ah, Reef Break, a show no one watched about a con artist-turned-fixer for hire who lives on a Pacific island and has a great time.
76.
Carmine Sabatini, The Freshman
Maybe you didn’t know that in 1990, Marlon Brando starred in a film about a guy who looks like Don Vito Corleone from The Godfather who enlists NYU Freshman Matthew Broderick to ferry exotic and endangered animals into New York so that they can be killed and served as expensive delicacies at the nomadic Gourmet food club he runs, but he did. Bruno Kirby co-stars.
75.
Gabriel Caine and Fitz Fitzpatrick, Diggstown
James Woods and Oliver Platt are partners in this odd movie about con men who try to fix boxing matches (Louis Gossett Jr is in it too). It’s not a good movie but there is strange to think about these three actors knowing the other ones exist.
74.
Angela and Wendy Nardino, Heartbreakers
Sigourney Weaver and Jennifer Love Hewitt play a mother-and-daughter con team whose aim is to seduce and con wealthy men. Angela (Sigourney) gets them to marry her, and Wendy (Jen) gets them to cheat so her mom can catch them, divorce them, and make off with their money. It’s actually a pretty good plan if its levels of mother-daughter bonding weren’t so… what.
73.
Sgt. Bilko, Sgt. Bilko
I love Steve Martin, but no one beats Phil Silvers at being Sgt. Bilko. Scroll down, please.
72.
Simon Silver, Red Lights
Red Lights is not a great movie, but Robert De Niro is nonetheless compelling as a fake psychic who resurfaces now that his most outspoken critic has disappeared.
71.
Barry Minkow, Con Man
In this movie also starring James Caan and Ving Rhames, Jane the Virgin’s Justin Baldoni plays a young Barry Minkow, the real con artist who became the CEO of a company by lying and cheating. Which, I’m sorry, differentiates him from many other big-time tycoons HOW?
70.
Nicky Spurgeon and Jess Barrett, Focus
This movie was supposed to star Ryan Gosling and Emma Stone as two con artists, and you can TELL! Their replacements Will Smith and Margot Robbie don’t have the same sparking chemistry.
69.
Steven Russell, I Love You Phillip Morris
Taking the phrase “be gay, do crimes” to new cinematic heights, I Love You Phillip Morris is a bit all over the place, but then again, when doesn’t a Jim Carrey movie feature a lot of bouncing off the walls? Plus, this one features lots of rattling prison bars. After Steven Russell (Jim Carrey) comes out as gay, he becomes a con man to support his more expensive lifestyle. But in jail he meets the love of his life, Phillip Morris (Ewan McGregor) and breaks out of jail to provide for him. Stereotypes aside, it’s pretty sweet.
68.
Richard and Rodrigo, Criminal
John C,. Riley plays Richard Gaddis, a super confident confidence man who recruits the petit-hustler Rodrigo (Diego Luna) into a large scheme. Rodrigo is the holy grail of con artists: he’s got a demeanor that is so sweet and genuine and guileless-seeming that no one believes he is tricking them. I too would believe anything Diego Luna tells me.
67.
Roy Courtnay, The Good Liar
In this thriller that summoned everyone’s grandparents to their local art house theater, Ian McKellen plays the silvertongued veteran con artist Roy Courtnay, who sets his sights on marrying millionaire widow Betty McLeish (Helen Mirren, who wouldn’t?) in a simple con. But things don’t go according to plan.
66.
Letty Raines, Good Behavior
Remember how after Downton Abbey Michelle Dockery did a 180 image-wise and starred in this TNT series about an ex-con con artist with self-destructive tendencies who takes it upon herself to save someone from being murdered? Still, Lady Mary would watch.
65.
Sophie Devereaux, Leverage
I’m not ashamed to say that I watched all five seasons of Leverage, a show about a bunch of professional crooks with different skills band together to help people in need and take down powerful, evil people or corporations. Everyone on the crew has different skills, but Gina Bellman’s Sophie is the only actual con artist (as opposed to a hacker, a thief, etc.). The joke is that she wants to be an actress, but she sucks unless she’s defrauding someone, in which case she’s a natural.
64.
Max Bialystock and Leo Bloom, The Producers
Look, Nathan Lane has flawless con-man energy. He’s incredible. But there’s no Producers like the original, even if this newer one is basically the same thing as the original Broadway musical.
63.
Bernie Madoff, Wizard of Lies
I worry that putting any avatar of Bernie Madoff (a real-life ponzi scheme architect with a name so on-the-nose even Charles Dickens would have found it too obvious) might suggest I think he’s cool. No. He’s a terrible human being. Robert De Niro plays him in this miniseries. That is all.
62.
Jordan Belfort, The Wolf of Wall Street
I mean, same? Great movie but… yeah, he sucks.
61.
Jonas Nightengale, Leap of Faith
Steve Martin plays Jonas Nightengale, a fake faith-healer and con artist, in this 1992 dark comedy which is basically a mash-up of The Music Man and Nightmare Alley. With, and this is the kind of fun bonus you’d be praying for, a very young Philip Seymour Hoffman!
60.
Bert Harris and Anne Roberts, Blonde Crazy
The fetishy title might not make it obvious that this movie is about a pair who pull off racket after racket, but it is! This 1931 classic stars James Cagney as conman Bert Harris who is in love with his accomplice Anne Roberts (Joan Blondell) but doesn’t realize he should make a move until she falls for another and marries him! Suddenly, he isn’t inspired to commit crimes anymore… until she comes back and needs his help. It’s crazy. Blonde crazy.
59.
Pirelli, Sweeney Todd: The Demon Barber of Fleet Street
Pirell, the brazen “Italian” barber who shows up to Fleet Street to sell a hair loss remedy, is one of the most shameless con artists on this list. (His snake oil is actually just urine. And he wants people to put it on their HEADS. ) Sacha Baron Cohen plays him in the Tim Burton adaptation of the Sondheim musical. And he’s so good at it you’ll just want to… eat him up.
58.
Juan and Marcos, Nine Queens
In Nine Queens, a 2000 Argentine crime film, con men Juan (Gastón Pauls) and Marcos (Ricardo Darín) team up to pull off a tremendous scam on a stamp collector.
57.
Big Dan Teague, O Brother Where Art Thou
John Goodman + the Coen Brothers = movie heaven. Or, I guess in the case of this movie which retells The Odyssey in the American South, it’s “movie Mount Etna,” since that’s the spot in the Odyssey where Odysseus meets the Cyclops. And Goodman’s Big Dan Teague is this film’s cyclops, a one-eyed fake Bible salesman and KKK member, a genuine bad guy.
56.
Robert and Theresa Dyne, Kajillionaire
Richard Jenkins and Debra Winger light up the screen as Evan Rachel Wood’s quirky small-time grifter parents in this charming new Miranda July film.
55.
Victor Mancini, Choke
Clark Gregg wrote and directed this movie based on the novel by Chuck Palahniuk about a man named Victor (Sam Rockwell, it’s a very Sam Rockwell role, just you wait) who struggles with sex addiction and works as a reenactor in a Colonial America experience but whose side hustle is pretending to choke on food in restaurants to con people out of money that he can use to pay for his mother’s Alzheimer’s care.
54.
Curly Sue and Bill, Curly Sue
John Hughes’s last film, about a homeless con artist (Jim Belushi) and the little girl who helps him in his schemes (Alisan Porter) who con a divorce lawyer into living with her, was panned, but, thanks to the chemistry of its two leads, has become a cult favorite since.
53.
Wichita and Little Rock, Zombieland
Emma Stone and Abigail Breslin are a sister con-artist duo at the end of the world in this enlivening film set during the zombie apocalypse. They should get their own prequel.
52.
Frank Bannister, The Frighteners
In this 90s Peter Jackson-Fran Walsh movie which pastiches horror films, Michael J. Fox’s Frank Bannister realizes he can communicate with the dead after his wife dies in a car accident and uses his friendships with ghosts to con people. His usual hoax? Sending the ghosts in to do some haunting, and then he exorcizes them away for profit. Which works for a while, until a certain ghost appears.
51.
Maddie Jonson, Impostors
Maddie is a dangerous femme fatale in this pretty good short-lived Bravo series Impostors; something of a Black Widow, she marries her marks before absconding with everything they have.
40.
Jason Staebler, The King of Marvin Gardens
In this fascinating Bob Rafelson film, Jack Nicholson plays a depressed late-night radio show host whose daydreaming con artist brother Bruce Dern gets him embroiled in a complicated get-rich-quick scheme. As always, Bruce Dern is incredible to watch.
49.
Philip Bang and Felice ‘Félix’ Brianza, The Con Artists
In this 1976 Italian film, titled Luff Storia di Truffe e di Imbroglioni, The Con Artists is a delightful buddy-comedy set in 1920s France. Philip (Anthony Quinn) and Felix (Adriano Celentano) are two ex-cons who team up together to swindle Philip’s nasty ex-wife Bella (Capucine) out of her money.
48.
Lee Israel, Can You Ever Forgive Me?
Melissa McCarthy plays Lee Israel, the real-life biographer of movie stars who, when she fell on hard times, perpetrated as scam “finding” typewritten letters from deceased Hollywood figures.
47.
Jimmy Dell, The Spanish Prisoner
In this David Mamet film about corporate espionage, Steve Martin plays a confident mastermind at the center of it all. A reminder that Steve Martin can play ANYTHING.
46.
Anna Delvey, Inventing Anna
We’re up to our ears in Anna Delvey by now, but just one more time: Inventing Anna is Netflix’s dramatization of the exploits of the Soho Grifter, in which Julia Garner flat-irons her hair and reinvents herself as the duplicitous hustler.
45.
Wayne and Dahlia Malloy, The Riches
I saw advertisements all the time for this two-season FX series when I was in high school, but only checked it out recently. Eddie Izzard and Minnie Driver play two nomadic Irish Travelers who assume the identity and home of a wealthy dead couple in the American south. And they have kids. It’s a whole family of impostors!
44.
Eli Kotch, Dead Heat on a Merry-Go Round
James Coburn plays a con man on parole who winds up coordinating an elaborate bank robbery. But the robbert is only a little part of the plan; the rest is him tricking women into giving him access to their money. So, even though this list doesn’t include theft, I’m making an exception because there’s so much other crookery going on.
43.
Wanda Gershowitz, A Fish Called Wanda
A Fish Called Wanda is an almost-perfect movie about four people (Jamie Lee Curtis, Michael Palin, Kevin Kline, and Tom Georgeson) who attempt to pull off a bank heist but wind up devising their own schemes to nab the loot and get off scot-free when one of their gang members is arrested, and it turns out that he’s the only one who knows where the loot is hidden. Jamie Lee Curtis is the only proper con artist among then, and she decides to try to seduce and fleece John Cleese, the lawyer working on the case, AND George, the thief who’s been arrested and knows the location of the jewels, AND Otto, her Nietzsche-reading, Aristotle-misunderstanding, gun-wielding, armpit-smelling Ugly American boyfriend.
42.
The Brothers Bloom, The Brothers Bloom
In this charming, offbeat adventure movie written and directed by Rian Johnson, Mark Ruffalo and Adrien Brody are brothers and con-men out for One Last Job, one that requires them targeting eccentric, lonely heiress Rachel Weisz and bringing her on a trip around the world. The plan involves faking their deaths and absconding with $2.5 million of her money while she flees pursuers who don’t technically exist. But she’s a lot smarter than they expect, and the adventure takes lots of turns for the surprising. It’s an enjoyable, clever movie that slips on different genre conventions at different times. Then again, Rachel Weisz all alone in her sprawling mansion, slightly crazy and learning tons of unconventional hobbies, might hit a little too close to home for us all, after spending months of quarantine.
41.
Myra and Bill Savage, Séance on a Wet Afternoon
Kim Stanley and Richard Attenborough are Myra and Billy Savage, married fraudsters who subsist on Myra’s fake-psychic act, until they realize they’ll get a bigger payout by kidnapping the child of a wealthy family, and relying on Myra’s “abilities” to find her, get the reward money, and become famous. One of the all-time movie titles, too.
40.
Marius Josipovic, Sneaky Pete
Giovanni Ribisi plays a conman attempting to hide from the angry gangster out to get him, and therefore assuming the identity of his former cellmate Pete Murphy. But he has to get in with Pete’s estranged family, which, turns out, could be even more dangerous!
39.
Chester and Colette MacFarland and Rydal Keener, The Two Faces of January
This 2014 adaptation of Patricia Highsmith’s classic 1964 novel The Two Faces of January is an entrancing tale of three duplicitous figures who abscond from Greece together after they are caught up in the death of a PI. It stars Viggo Mortensen, Kirsten Dunst, and Oscar Isaac, so yeah, you should really watch it.
38.
Stanton Carlisle, Nightmare Alley
Bradley Cooper plays our protagonist, the phony psychic Stanton Carlisle, with greedy vigor in Guillermo Del Toro’s adaptation of the William Lindsay Gresham novel. I prefer Tyrone Power in the part (see below), but Cooper does bring a genuine hunger to the character.
37.
Remington Steele, Remington Steele
I love Remington Steele, even despite its narrative weirdness regarding the erasure of women’s labor… Stephanie Zimbalest plays a PI who creates the fictitious male alter-ego Remington Steele to get more business, and then a former thief/con man shows up claiming to be Remington Steele. (It’s a young Pierce Brosnan.)
36.
Mike Mancuso, House of Games
Joe Mantegna is the perfect con man in this intricate David Mamet thriller. You know who’s on this list a lot? David Mamet. David Mamet and Steve Martin.
35.
Irving Rosenfeld and Sydney Prosser, American Hustle
I find David O. Russell’s American Hustle to be pretty overrated, but both Christian Bale and Amy Adams act their hearts out as a pair of hustlers manipulated by a petulant FBI agent (Bradley Cooper) into a massive sting operation. Someone please just give Amy an Oscar.
34.
Marilyn Rexroth, Intolerable Cruelty
Catherine Zeta-Jones is delightful as a vengeful, goldigger-femme fatale in this entertaining yet oft-maligned Coen Brothers screwball comedy, in which she does battle with George Clooney’s arrogant divorce lawyer.
33.
Paul “Poitier”, Six Degrees of Separation
Six Degrees of Separation, the film adaptation of John Guare’s Pulitzer Prize-nominated 1990 play, is a very complicated movie when it comes to race and class and sexuality and it deserves a much longer reflection than the blurb I’m assigning to it here. Will Smith is amazing as the con man pretending to be Paul Poitier, the Harvard-educated son of actor Sidney Poitier, and ingratiating himself into the homes of his “classmates’” wealthy, white families.
32.
Lyle Lanley, The Simpsons
The great Phil Hartman provides the voice of this crooked traveling monorail salesman in The Simpsons’s Music Man tribute, one of the show’s very best episodes.
31.
Mordecai Jones, The Flim-Flam Man
In this comedy brimming with different kinds of schemes, George C. Scott plays a traveling charlatan named Mordecai Jones. Mordecai has some pretty impressive qualifications that make him the right man for this list: “M.B.S., C.S., D.D.” (Which stands for “Master of Back-Stabbing, Cork-Screwing and Dirty-Dealing!” So, welcome home, Mordecai.)
30.
Dimitri and Vlad, Anastasia
You find me an animated character more swooned-over in the 90s than John Cusack’s Dimitri. I’ll wait. He and his assistant, Kelsey Grammar’s Vlad, are trying to find a Princess Anastasia lookalike to pass off as the real lost princess, and don’t realize exactly that they’ve stumbled across the real thing when they meet the amnesiac Anya.
29.
Harry the Hat, Cheers
Everyone’s favorite magician-actor Harry Anderson plays the small-time con man who pops into the Cheers bar every now and again and it’s the best cameo in the show.
28.
Gavin Volure, 30 Rock
To leave 30 Rock’s pathetic huckster (Steve Martin) off this list would be to seriously miscount the men, Liz!
27.
Nam Sook-hee, The Handmaiden
I’ve been on about the greatness of Park Chan-wook’s The Handmaiden is a Dickensian con-artist erotic thriller set in South Korea and if that description alone doesn’t sell you, then I don’t know what you are doing here. Kim Tae-ri plays Nam Sook-hee, a pickpocket under the thumb of master conman “Count Fujiwara,” who is sent (in disguise as a maid) to help him gain access to the wealthy heiress Lady Hideko (Kim Min-hee), whom he plans to marry and then commit to an asylum! But things go awry when Lady Hideko and Sook-hee fall in love.
26.
Stanton Carlisle, Nightmare Alley
The rise and fall of Tyrone Power’s fake psychic is riveting here, especially because he starts out curious and earnest and becomes more and more contemptible as he reaches the big time.
25.
Oda Mae Brown, Ghost
Whoopi Goldberg won an Oscar for playing the gutsy fake-psychic (with real abilities that she doesn’t really know about yet) Oda Mae Brown in the Patrick Swayze erotic-haunting movie Ghost. And you know what? Her performance is DIVINE.
24.
Freddie Benson and Lawrence Jamieson, Dirty Rotten Scoundrels
Michael Caine and Steve Martin are two rival con men in a race to see who can swindle an American heiress out of her fortune, in this rollicking comedy set along the French Riviera. A duel of smarm like you’ve never seen before!
23.
Shelley Levene, Richard Roma, George Aaronow, Dave Moss, and Blake, Glengarry Glen Ross
Ah, Glengarry Glen Ross, the only movie that will break your heart by being about shady real estate salesmen who are growing too old and becoming out of touch to pull off their schemes.
22.
Professor Marvel, The Wizard of Oz
Frank Morgan’s Professor Marvel, a kindly traveling performer and hoodwinker, is the basis for the Wizard himself in Dorothy’s dream. It’s not easy to walk the line between lovable and pathetic, and he jumps up and down on it.
21.
Madam Blanche Tyler, Family Plot
Barbara Harris plays phony-psychic Blanche Tyler searching for the nephew of a wealthy heiress in this late-career Hitchcock movie about two criminal couples whose plans cross with complicated results. When Harris is on screen, you can’t look away: she has a sweet, sleepy-voiced delivery that will make you believe everything she’s saying
20.
Jules Amthor, Murder My Sweet
Everybody lies in a Philip Marlowe story, it just goes with the turf, but Otto Kruger’s debonair fake healer Jules Amthor takes things to a whole new level of deceit in this stone-cold classic from 1944 starring Dick Powell.
19.
Michael “Mickey Bricks” Stone, Albert Stroller, Ash “Three Socks” Morgan, Stacie Monroe, and Danny Blue, et al, Hustle
If you like con artists, you should watch Hustle, the British series about a group of expert bamboozlers who pull off long cons. Everyone is super cool, and the dynamics between the characters who embody different schools of “cons” is fascinating!
18.
Saul Bloom, Ocean’s Eleven, Ocean’s Twelve, and Ocean’s Thirteen
The great Carl Reiner plays an elderly con man who rounds out ‘the burglar’s dozen’ in the Ocean’s movies. Everybody has a different job on the team, and Saul is the only one whose expertise is specifically, squarely as a con man (as opposed to a grease man, a munitions expert, a financier, etc.). I could watch Carl Reiner all day.
17.
Max Bialystock and Leo Bloom, The Producers
Can we just take a moment to appreciate how perfectly Mel Brooks (who won an Oscar for writing the 1967 screenplay) presented the film’s central gambit in dialogue? INDULGE ME.
Leo Bloom: Let’s assume, just for the moment, that you are a dishonest man.
Max Bialystock: Assume away.
Leo Bloom: It’s very easy. You raise more money than you need.
Max Bialystock: What do you mean?
Leo Bloom: Well, you did it yourself, only you did it on a very small scale.
Max Bialystock: What did I do?
Leo Bloom: You raised $2,000 more than you needed to produce your last play.
Max Bialystock: So? What did it get me? I’m wearing a CARDBOARD BELT
Leo Bloom: Well, that’s where you made your mistake: you didn’t go all the way. You see, if you were a truly bold criminal, you could’ve raised a million.
Max Bialystock: But the play cost me only $60,000 to produce!
Leo Bloom: And how long did it run?
Max Bialystock: One night.
Leo Bloom: You see? You see what I’m trying to tell you? You could’ve raised a million dollars, put on your $60,000 flop, and kept the rest.
Max Bialystock: But what if the play was a hit?
Leo Bloom: Well, then you’d go to jail. See, once the play’s a hit, you have to pay off all the backers, and with so many backers, there could never be enough profits to go around. Get it?
Max Bialystock: Uh-huh. A-ha! So, in order for this scheme to work, we’d have to find a sure-fire flop!
Leo Bloom: What scheme?
Max Bialystock: What scheme! YOUR scheme, you bloody little genius!
There have been a lot of Bialystocks and Blooms since 1967, but nobody does them better than Zero Mostel and Gene Wilder, and that is the honest truth.
16.
Sgt. Ernie Bilko, The Phil Silvers Show
The thoroughly unique comic genius Phil Silvers lit up every single project he touched, and his Sgt. Bilko, the man in charge of an army base where nothing really happens, is one of the greatest small-time grifters. Phil Silvers’s specialty was slightly-slithery, slippery, but gutsy and blustery characters. Bilko’s shenanigans, constantly trying to fleece whoever he can for however much he can, provided the perfect playground. “The King of Chutzpah” strikes again!
15.
Harry Powell, The Night of the Hunter
Charles Laughton’s only film is Night of the Hunter, a masterpiece about a psychopathic con artist, serial-killer, self-appointed preacher named Harry Powell (Robert Mitchum, always great, never better), who, when he gets out of jail, becomes obsessed with finding the money hidden by his lately-executed bank robber former-cellmate—a secret which is kept by the robber’s two young children. The performance OF A LIFETIME.
14.
Moses Pray and Addie Loggins, Paper Moon
Tatum O’Neal won a Best Supporting Actress Oscar for her portrayal of Addie Loggins, a precocious kid initially used in a get-rich-quick scheme by small-time con man Moses Pray (Ryan O’Neal, her real-life father) who ultimately joins in his schemes, as the two drive through the Depression-Era Midwest. They are a pair you’ll never forget.
13.
Kim Ki-taek, Kim Chung-sook, Kim Ki-jung, and Kim Ki-woo, Parasite
Bong Joon-ho’s Parasite is a towering, terrifying satire of class and capitalism, told through the eyes of the Kim family, desperate to climb out of brutal poverty in Seoul. It’s incredible for a million reasons, but mostly for the pathos of the Kims. And “JESSICA~ONLY CHILD~ILLINOIS~CHICAGO.”
12.
Neal Caffrey and Mozzie, White Collar
I love White Collar and so does everyone else who has a heart and access to the USA network. Matt Bomer is Neal Caffrey, a suave conman/forger/thief who winds up serving out his prison sentence by solving crimes with the FBI. Neal has been arrested for bond forgery (although suspected of numerous other crimes, including art forgery and theft, money laundering, confidence schemes, and racketeering), but he is mostly an old fashioned con man. Although his partner in the show is Peter Burke (Tim DeKay), his uptight FBI agent handler with whom he strikes an unusual friendship, his partner in cons is Mozzie (Willie Garson), an eccentric, socially-awkward genius who loves conspiracy theories and wine. Mozzie helps Neal with his own side hustles, but also helps him and Peter nail people who don’t use fraud as kindly: crooked hedge fund managers, Wall Street psychopaths, Ponzi schemers, corrupt diplomats, extortionists… you get the picture.
11.
Lilly Dillon, Roy Dillon, and Myra Langtry, The Grifters
Angelica Huston, John Cusack, and Annette Benning are (respectively) mother, son, and son’s girlfriend—all tough-as-nails swindlers—in this classic neo-noir directed by Stephen Frears, produced by Martin Scorsese, and screenwritten by Donald E. Westlake, based on the 1963 novel by Jim Thompson. With that pedigree, it’s impossible for this movie to be a sham.
10.
Roy Waller and Frank Mercer, Matchstick Men
Nicolas Cage gives one of his best performances as Roy Waller, a con artist with severe OCD and Tourette’s. Sam Rockwell is his protege Frank. Go watch it.
9.
Jean Harrington, The Lady Eve
Has anyone been more of a real broad than Barbara Stanwyck? Man. In this 1941 Preston Sturges comedy, she lights up the screen as the hardball-playing Jean Harrington, aka Lady Eve Sidwich, who plans to seduce and grift a fellow passenger on an ocean liner: Charles Poncefort Pike (Henry Fonda, of all people), a herpetologist with a pet snake who is also afraid of women. ALL. ABOARD.
8.
Billy Ray Valentine, Trading Places
Eddie Murphy’s Billy Ray Valentine is so legendary as a con artist that there’s a real-life legal protection named after him, which bans “using misappropriated government information to trade in the commodity markets,” as happens in the film. Icon.
7.
Elmer Gantry, Elmer Gantry
Okay, he’s a bit intense and the concept is scary but wow, Burt Lancaster could sell me my own house.
6.
Arthur Simon Simpson, Topkapi
Peter Ustinov won an Oscar for his delightful portrayal of Arthur Simon Simpson, a small-time, very English con artist who falls in with a group of thieves pulling off a nearly impossible museum heist in Istanbul.
5.
Jimmy McGill, Better Call Saul
Better Call Saul’s Jimmy McGill (aka Breaking Bad’s Saul Goodman) is one of the absolute best characters to come out of the last decade or so of television, the con man/lawyer who’s number one on your speed dial right next to your weed dealer.
4.
“Fast Eddie” Felson, The Hustler
THE HUSTLER. God, what a movie. I’d watch Paul Newman’s portrayal of the unfocused, small-time-but-gifted-pool-hustler Eddie determined to take down Jackie Gleeson’s legendary billiards champ Minnesota Fats every day of the week.
3.
Harold Hill, The Music Man
Whaddya talk, whaddya talk? Robert Preston gives one of the greatest performances in movie musical history as Harold Hill, a “fly-by-night” traveling salesman who convinces entire towns to buy marching band programs for the local youth, and then absconds with the money. In the words of one of the (honest) traveling salesmen who has heard about him, “…the fellow sells bands, Boys’ bands/I don’t know how he does it but he lives like a king/And he dallies and he gathers and he plucks and he shines/And when the man dances certainly, boys, what else? The piper pays him!” YES SIR. YES SIR. YES. SIR
2.
Frank Abagnale, Jr., Catch Me If You Can
Leonardo DiCaprio is teenage fraudster and forger Frank Abagnale, Jr in this really fun and also very sad story of extreme talent and crushing loneliness, about a prodigy from a broken home who travels the world, forging documents and assuming identities.
1.
Henry Gondorff and Johnny Hooker, The Sting
Look, maybe I’m a bad bluffer, but it’s not terrible if you knew all along that Gondorff and Hooker were going to be my aces here. Number one. Okay, JJ, deal me out.
