It’s Friday, the weekend is here and turkey sandwiches are fast approaching. Sitting down with your family on Sunday night for Thanksgiving, the memories of past dinners bubble to the surface. It’s all very loving in a Home Alone, far too many people sitting at the dinner table, type of way.

Then after dinner, once dessert and coffee have been dished out and conversation has lulled (maybe grandpa fell asleep in the corner) it’s time to watch a movie! Gather the family around the TV, throw some popcorn in the microwave, and put on a flick that everyone can enjoy. But because we deal with fraud on a daily basis here at Canadian Fraud News, the movie should definitely be fraud, con or scam related.

So here at CFN we’ve created a list of the top five fraud movies to watch with your family. A few are outlandish and completely unrealistic, and some have shades of truth to them (the phrase“based on a true story” popping up everywhere.)

Catch Me if You Can

What do you get when you have Leonardo Dicaprio, Tom Hanks and Steven Spielberg all collaborating on a project? Well you end up with one of the best films about fraud and scams ever created. Dicaprio plays real life con man Frank Abagnale, with Hanks as the FBI agent tasked with catching him. While the scams seem outlandish, the film is pretty faithful to real life events and Spielberg capture it all with a sense of whimsical innocence that makes for a fun, fascinating watch.

Wizard Of Lies

One of the newer entries on this list, Wizard of Lies explores the rise and fall of the infamous Bernie Madoff. And who better to play the cold and calculating king of Wall Street than Robert De Niro himself? Wizard of Lies works well the depiction of his ponzi scheme and therefore the fraud elements feel tangible and terrifying. This film in particular is a great because it explores  consequences of Madoff’s actions in connection with his family, and the other very real people involved. It never asks you to sympathize with Madoff, but only to try and understand him. Something in and of itself is practically impossible to do.

Owning Mahowny

As a Canadian cult classic (and CFN favourite) this gem starring the late Philip Seymour Hoffman recounts the biggest case of Canadian bank fraud in the country. As vice-president of a Toronto bank, Mahowny only steals as much as he needs to pay off his gambling debts ($10,300). But eventually things spiral out of control and he ends up taking his bank for $10.3 million. Funny and irreverent, this one plays fast and loose with how exactly it all happened, but it’s still a great depiction of a desperate man in a desperate situation (and it doesn’t hurt that it’s set against the Toronto skyline). The script is tack sharp and the atmosphere feels believable, which adds to the overall believability.

Enron: The Smartest Guys In The Room

This is a fascinating documentary that follows the shady business practises and policies of the Enron corporation. It’s a film that will set your teeth on edge. Engrossing and finely tuned, the documentary explores the notion that Enron was a good company gone bad, stating that in fact it was a giant scam right from the get go. It’s almost painful to watch these people and their lack of empathy for how their actions affected thousands of people. Smartest Guys In The Room is a fantastic documentary to watch for those with both a vast understanding of the situation and those who don’t know much of what happened at that time.

Boiler Room

This move is about as hollywood as it gets. With a star-studded cast that includes Giovanni Ribisi, Vin Diesel and a young Ben Affleck, Boiler Room is bombastic and slightly ridiculous. But it also has one of the best angry “I’m an important person,” speeches ever put to film, that Affleck delivers with sinister charm. Is it at all realistic to how scams and fraudulent situations happen? Not really. Are the characters interesting and three-dimensional? Not really. But is it a ton of fun from start to finish? Oh hell yes. Boiler Room also includes a cheesy and over the top soundtrack that’s straight out the early 2000s and it’s a treat to revel in. 

Honourable Mentions

Wolf Of Wall Street – Everybody knows this one. It’s fun and ridiculous and needlessly over the top.

The Hustler – A cinema classic that everyone needs to see, we didn’t put it in our top five because it doesn’t directly deal with frauds or scams. Although Paul Newman is so good you could make the case on his performance alone.

Rounders – Two stellar performances from Matt Damon and Edward Norton in a movie about scamming people during a poker game. What’s not to love? Also look for John Malkovich as a crazy russian gangster who sets up the high stakes game.

Inside Man – In my opinion this is Spike Lee’s most underrated movie to date. Denzel Washington is absolutely fantastic in this game of cat and mouse between a detective and world class con man. Watch all the way to the very end for a twist that will blow your mind.

Read our first original reporting here.