25 money movies (that actually stream in Canada)

Working Girl is streaming on Disney+ and is available for rent on Prime Video.

The Insider (1999)

Al Pacino and Russell Crowe lead this tense drama, based on the true story of a tobacco-industry cover-up and the whistleblower who brought it to light. Masterfully directed and co-written by Michael Mann, the film also looks at the questionable journalistic ethics of a controversial 60 Minutes segment about Jeffrey Wigand, the aforementioned whistleblower. —Jaclyn Law

The Insider is available for rent on Prime Video.

Boiler Room (2000)

Ben Affleck, Vin Diesel and Giovanni Ribisi are some of the familiar faces you’ll see in this fast-paced drama set in a shady New York brokerage firm. The “boiler room” is the call centre where ambitious young sales reps, eager to make their first million, push questionable stocks on an unsuspecting public. Critic Roger Ebert said the movie “hums with authenticity” and “has the high-octane feel of real life, closely observed.” —J.L.

Boiler Room is available for rent on Prime Video and Apple TV+.

American Psycho (2000)

The film adaptation of the Bret Easton Ellis novel is a black comedy that equates the toxically masculine world of high finance and yuppie consumerism in the 1980s with serial murder. In one of his iconic roles, Christian Bale plays Patrick Bateman, an investment banker who obsesses over outward signs of success (business cards, cufflinks) by day and butchers bodies by night. Eventually, it becomes hard to keep the blood off his crisp business shirts, yet he’s abetted by enablers to the end. —Michael McCullough

American Psycho is streaming on Netflix and Tubi.tv.

The Corporation (2003)

This Canadian-made documentary is the best kind of polemic, in that it awakens viewers to many little-known facts about how modern capitalism really works, which is to say not in the interests of ordinary people. Co-written by University of British Columbia law professor Joel Bakan, it’s an antidote to all the happy language found in annual reports and advertising. Still, as with that corporate messaging, you’ll come away from The Corporation feeling as if you’ve got only half the story. For starters, the film dwells on the negative “externalities” of corporate behaviour (exploitation of workers, subversion of state sovereignty, environmental degradation) without once mentioning the positive ones, such as job creation, productivity improvements and the wealth generation that funds pensioners’ and investors’ retirements. Also check out The New Corporation: The Unfortunately Necessary Sequel (2020), streaming on Crave. —M.M.

The Corporation is available for rent on Apple TV+.

Owning Mahowny (2003)

Owning Mahowny is a seldom-watched gem in the late Philip Seymour Hoffman’s sparkling oeuvre. Hoffman plays Dan Mahowny, a schlubby suburban banker who embezzles ever-greater sums from his employer to fuel his gambling addiction. The story is based on that of Brian Molony, a former CIBC employee in Toronto convicted of stealing more than $10 million over 18 months. Watching the movie helps you understand that addictive behaviour doesn’t require substance abuse. The lure of easy money will do the trick. —M.M.

Owning Mahowny is streaming on YouTube.

Enron: The Smartest Guys in the Room (2005)

Move over, financial movies. Financial docs have all the drama and the finger-pointing you want from a flick. This documentary examines the rise and catastrophic fall of Enron, one of the largest corporate bankruptcies in U.S. history. Through interviews and real-life footage, it reveals the corruption and ethical issues that led executives to manipulate energy prices, commit widespread fraud and deceive investors. —L.H. 

Enron: The Smartest Guys in the Room is streaming on Plex. 

The Social Network (2010)

This highly watchable dramatization of Facebook’s origin story may be a character assassination of Mark Zuckerberg (the Winklevoss twins, by contrast, come off no worse than subsequent headlines would suggest). But it’s a reminder that companies—indeed, the way technology and the economy evolve—are influenced by often petty human motives. Jesse Eisenberg portrays Zuckerberg as being somewhere on the autism spectrum yet full of self-righteous spite. Recommended viewing for any aspiring entrepreneur. —M.M.

The Social Network is streaming on Crave.

Wall Street: Money Never Sleeps (2010)

In this sequel to the 1987 film Wall Street, Michael Douglas plays Gordon Gekko, a disgraced corporate raider who was released from prison after serving time for insider trading and securities fraud. The film, set during the 2008 financial crisis, follows Gekko as he attempts to repair his relationship with his estranged daughter Winnie (Carey Mulligan) and becomes a father figure to her fiancé, a young stockbroker named Jacob Moore (Shia Lebouf). As the plot takes shape, those around him must decide if Gekko is reformed, or the greed-driven man he always was. —Justin Dallaire

Wall Street: Money Never Sleeps is streaming on Apple TV+.

Inside Job (2010)

Inside Job was the first movie to tackle the 2008 global financial crisis. This Oscar-winning documentary explains what led to the worst economic downturn since the Great Depression—from financial-industry deregulation in the 1980s through to subprime mortgages and the collapse of the American housing market. Narrated by Matt Damon, Inside Job uses interviews with economic experts, Wall Street insiders, government officials and academics to explain the origins of the crisis and sound a warning to future generations. —J.L.

Inside Job is streaming on Tubi.tv and available for rent on Prime Video.

Too Big to Fail (2011)

One of several films about the 2008 financial crisis, Too Big to Fail is a dramatization that focuses on government and banking leaders, including Treasury Secretary Hank Paulson (William Hurt), former Lehman Brothers CEO Richard Fuld (James Woods), Federal Reserve chair Ben Bernanke (Paul Giamatti) and others, from late March to October 2008 as they try to mitigate the global financial meltdown. —J.L.

Too Big to Fail is streaming on Crave.

Margin Call (2011)

This star-studded drama depicts 24 hours at a fictional New York investment firm (think Goldman Sachs or Lehman Brothers) on the cusp of the 2008 financial crisis. A junior analyst realizes that the firm has too much exposure to mortgage-backed securities—a situation that could bankrupt the company. He notifies his superiors, setting off a series of decisions that challenge the business and personal ethics of everyone on the team. The cast includes Jeremy Irons, Kevin Spacey, Stanley Tucci, Demi Moore, Paul Bettany, Zachary Quinto, Topher Grace and other famous faces. —J.L.

Margin Call is streaming on Prime Video.

Arbitrage (2012)

This American crime drama follows successful hedge fund manager Robert Miller (played by Richard Gere), who is desperately trying to sell his fund to a big bank before it’s too late. Miller is perpetrating a fraud involving millions in borrowed funds and covered-up investment losses. A deadly accident puts his scheme at risk, and Miller must juggle overcoming his personal and financial missteps to escape. —J.D. 

Arbitrage is streaming on Prime Video and Tubi.tv.

The Wolf of Wall Street (2013)

The Wolf of Wall Street is based on the true story of Jordan Belfort (played by Leonardo DiCaprio) and his life of excess in the 1990s running his firm, Stratton Oakmont. It follows his life as an ambitious broker selling penny stocks to a multimillionaire married to Naomi Lapaglia (played by Margot Robbie) and launching the IPO for shoe magnate Steve Madden. The over-the-top drug scenes aren’t for the faint of heart, but they do deliver shocking laughs. —L.H.

The Wolf of Wall Street is available for rent on Prime Video.

American Hustle (2013)

David O. Russell directed this dark comedy about a pair of grifters (Christian Bale and Amy Adams) who are forced into a risky sting operation by FBI agent Richie DiMaso (Bradley Cooper), after he catches them running a loan scam. DiMaso’s target: Carmine Polito (Jeremy Renner), a corrupt mayor in New Jersey. Jennifer Lawrence also co-stars in this Oscar-nominated flick, which was based on a real-life FBI case dating back to the late 1970s. —J.L.

American Hustle is available for rent on Prime Video.

The Big Short (2015)

The Big Short is an Oscar-winning financial drama that portrays the 2008 housing market crash through the eyes of several outsiders who saw the collapse coming. Based on the 2010 book by Michael Lewis, the film follows eccentric investors who bet against the subprime mortgage market, revealing the corruption and recklessness that led to the global financial crisis. —L.H.

The Big Short is streaming on Apple TV+ and available for rent on Prime Video.

Equity (2016)

Equity is a financial thriller about ambitious Wall Street investment banker Naomi Bishop (played by Breaking Bad’s Anna Gunn), trying to prove herself and earn a promotion by taking a social media start-up public. But complications—both professional and personal—arise. Should Naomi investigate, at the risk of torpedoing the deal? Equity explores ethics, gender dynamics and the price of success. It’s also notable for being the first Wall Street drama written, financed, produced and directed by women. —J.L.

Equity is streaming on AppleTV+.

The Founder (2016)

Whether or not you deign to eat at McDonald’s, you might enjoy The Founder—an entertaining flick about burgers, capitalism and innovation. The film is a biopic about Ray Kroc (Michael Keaton), an ambitious salesman who grew McDonald’s—which started out in 1940 as a single hamburger stand in California—into a global fast-food behemoth, forever changing America’s restaurant industry in the process. —J.L.

The Founder is streaming on Netflix.

The Laundromat (2019)

Steven Soderbergh’s satirical drama The Laundromat—starring Meryl Streep, Gary Oldman and Antonio Banderas—dives into the complicated world of money laundering. The plot is based on a book about the Panama Papers, which revealed how the world’s ultra-wealthy hide their riches in offshore accounts. Told in an episodic fashion, with characters frequently breaking the fourth wall to explain what’s going on, The Laundromat attempts to show the effects of financial-system corruption on everyday people. —J.L.

The Laundromat is streaming on Netflix.

The Banker (2020)

Set in the 1960s, The Banker is inspired by the true story of two African American entrepreneurs, Bernard Garrett (Anthony Mackie) and Joe Morris (Samuel L. Jackson). The pair of real estate investors confront racial discrimination as they set out buying properties to sell to Black families in segregated neighbourhoods. Ultimately, they decide to hire a working-class white man (Nicholas Hoult) with no banking experience to be the face of their empire—a decision that leads to serious legal troubles. This Apple TV original movie was directed, co-written and produced by George Nolfi. —J.D. 

The Banker is streaming on Apple TV+.

Nomadland (2020)

Fern (played by Frances McDormand) is a widow in Nevada who hits the road in search of employment, after the sheet-rock mine where she and her husband worked for decades shuts down in the wake of the Great Recession. Fern becomes one of countless itinerant older Americans travelling across America in search of seasonal work. Nomadland is a moving and eye-opening look at grief, financial insecurity and economic upheaval. It won three Oscars in 2021, including best picture, best actress and best director. —J.L.

Nomadland is streaming on Disney+ and available for rent on Prime Video.

I Care a Lot (2021)

I didn’t like this movie. Not because it wasn’t good, but because I didn’t enjoy how it showed how vulnerable seniors (and me, eventually) can be. Rosamund Pike portrays Marla Grayson, who poses as a guardian for the elderly to ultimately control their lives and drain their assets. That’s until she targets Jennifer Peterson (Dianne Wiest), who turns the tables on Grayson. —L.H. 

I Care A Lot is streaming on Netflix and Prime Video.

Dumb Money (2023)

This meme-stock flick, based on the 2021 GameStop short squeeze, has all the trader tropes you want: the out-of-touch but incredibly wealthy fund managers, bikini pool parties, a comedian cameo (Pete Davidson) and more. But there are a few characters that stand out: financial analyst Keith Gill (a.k.a. Roaring Kitty, played by Paul Dano), nurse Jenny (America Ferrera) and other middle-class holders of “dumb money” (a.k.a. uninformed investors). It’s a compelling story that challenges the idea that “retail investors never win.” —L.H.

Dumb Money is streaming on Prime Video.

Blackberry (2023)

BlackBerry tells the behind-the-scenes story of the rise and fall of Research in Motion (RIM), the company behind the iconic BlackBerry smartphone. While the company’s fortunes (and misfortunes) are central to the plot, the film could be described as a biographical drama of co-founders Mike Lazaridis and Jim Balsillie. The movie, which was also made into a three-part mini-series (streaming on CBC Gem), highlights the challenges BlackBerry and its founders faced as competitors and changing technology eroded RIM’s dominance. —J.D.

Blackberry is streaming on Apple TV+.

Jackpot! (2024)

You know how some people will see a movie just for the star, like Brad Pitt or Tom Cruise? That’s Awkwafina for me. And as a fan of her sitcom Nora from Queens, I immediately watched the comedy Jackpot! when it showed up on my recommended watchlist. She plays Katie Kim, who wins a $3.6-billion lottery prize—except that her winnings are transferable to someone who kills her. So, she hires a freelance bodyguard, Noel Cassidy (played by Jon Cena), and they race to get her winnings. It’s silly. It’s fun. And it makes fun of dystopian movies, which is a welcome escape in this economy. —L.H.

Jackpot! is streaming on Prime Video.

About MoneySense Editors

MoneySense editors and journalists work closely with leading personal finance experts in Canada. Since 1999, our award-winning magazine has helped Canadians navigate money matters.

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