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