The Seven Best Con Artists in Movies

I’m a big fan of movies that tend you throw you for a loop.  Whether the whole movie is a con or just a small part of it is, it’s a great concept and something that can keep all of us on edge.   It’s something I just don’t think movies do these days.  Today it’s all about visuals and stories are less important.

Which is why today I wanted to focus on con artists in movies.   When portrayed right, and acted right, they can be a real treat.

Here are seven of my favorite.   Be careful folks, there are spoilers ahead…..

Roy Waller in Matchstick Men

I personally think this is one of Ridley Scott’s last good films.  Nicholas Cage and Sam Rockwell work together to pull off scheme after scheme.  Only things get difficult when Nicholas Cage discovers he has a daughter and he has to try to pull off one his biggest cons ever.  Or is she even his daughter?  Ahhh, we just don’t know do we?  Anyway, his depiction of a OCD wacko con man Roy Waller is a fine performance.  One I thought he could have gotten Oscar nomination for.

Roy Dillon in The Grifters

Played by John Cusack, Roy Dillon is pretty small time compared to his mom Lilly (Angelia Houston) but he is put to the test after a series of bad incidents.  After he is released from the hospital, Roy and Myra (his girlfriend) go on a little trip, where he is propositioned to be partners in crime with Myra.  Everything soon falls apart for the three con artists, which leads to a bloody climax.

Jake Vig in Confidence

Taken directly from IMDB – What Jake Vig doesn’t know just might get him killed. A sharp and polished grifter, Jake has just swindled thousands of dollars from the unsuspecting Lionel Dolby with the help of his crew: Insideman Gordo, Shills Miles, and Big Al–and two corrupt LAPD officers, Lloyd Whitworth and Omar Manzano. But when both Lionel and Big Al turn up dead, it becomes clear that Lionel wasn’t just any mark–as Jake soon learns, he was an accountant for eccentric crime boss Winston King. Never one to shy away from a challenge, Jake offers to repay The King by pulling off the biggest con of his career

Frank Mercer in Matchstick Men

While Nicolas Cage deserves credit for his Roy Waller, the real winner in this movie is Sam Rockwell’s character Frank Mercer.   Frank appears to be the protege the entire time but we find out that the entire movie is a con set up by Mercer to rob Waller of all his money.   Pretty awesome when you think about it.

Henry Gondorff in The Sting

Two men work together to seek revenge on a man who is responsible for the death of one of the greatest con men mentors of all time.  Gondorff, played by Paul Newman is a legend in the con game.   The scenes where he plays cards with a notorious gangster and just about every other scene are incredibly memorable.   And of course you’ve got Robert Redford to boot.   What they pull off in the end is one of the most famous movie cons of all time.

Lawrence Jamieson in Dirty Rotten Scoundrels

A crappy con man played by Steve Martin thinks he knows what he’s doing in terms of swindling money from unsuspecting women.  But he’s met his match in Michael Caine, who not only does this for a living, but has made a fortune doing so.   I chose Caine here because Martin is still small time.  Well, both of them are solid until they meet their match: a women they try to con who actually has the last laugh.

*Frank Abagnale in Catch me if you Can

I put a star next to this name because Abagnale is a real person.   Still though, that doesn’t mean he shouldn’t be on this list.  DeCaprio does a great job of portraying the man who posed as a Pan Am pilot and swindled over 2 million dollars in fake checks.  The cat and mouse chase and humor of Tom Hanks and Leonardo DiCaprio is awesome.  Oh yeah, and having it directed by Steven Spielberg is a plus.

*Honorable Mention to Janet Colgate (Dirty Rotten Scoundrels), Freddy Benson (Dirty Rotten Scoundrels), and Johnny Hooker (The Sting), Lilly and Myra (The Grifters)

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  1. No Ocean’s Eleven (The 2001 version)? Best robbery in the history of movies. You put Roy Waller (who was being fooled the entire movie) and left out the guys who robbed THREE cassinos at the same time and walked out through the front door? Your list fails, good sir.

  2. Would like to have seen Keyser Soze in there though I can see the reasoning for leaving him out since the movie isn’t straight up about con-men like the others here.

  3. I agree with Andre. Although it was all building up to the robbery at the end, there was still a considerable amount of conning going on throughout the movie.

  4. Andre, they only robbed one casino in Ocean’s 11 (that of Benedict). Ocean’s 13 is where they robbed three casinos simultaneously, and that movie shit.

    Furthermore, Danny Ocean wasn’t really a con man like the rest of the guys in this list. He merely pulled off a big caper, a daring robbery. Not the same as a “con”fidence type of crime.

  5. What about the guy from ‘I Love You Phillip Morris’?
    I kinda liked that movie. Also a real person.

    Yep, I’m actually too lazy to Google his name.

  6. this list is pretty mediocre. there’s so many great con movies out there and you pick 2 characters from the mediocre matchstick men and you actually include confidence?

    ever seen the usual suspects?
    jackie brown?
    six degrees of separation?
    paper moon?
    house of games?
    brothers bloom?

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