Year-end is always a strange mix of pause and stock-taking. For anyone sitting in a decision-making chair in a company under regulatory, financial or reputational pressure, it’s hard to “switch off” completely. One way out is to use the break to look at corporate crisis from a different angle – through fiction. The list below brings five films about companies under stress, greed, governance failures and difficult choices. This is not a class on corporate criminal law, but each title helps you see, from a safer distance, dilemmas that look uncomfortably similar to what ends up on your desk.
Wall Street (1987)
An absolute classic of the genre, directed by Oliver Stone and starring Michael Douglas (who won the Oscar for Best Actor), together with Charlie Sheen and Martin Sheen. Wall Street follows a young broker fascinated by the power and access of Gordon Gekko. Without pretending to be a manual on capital markets, the film shows how the pursuit of results at any cost erodes ethical boundaries, normalizes illegal shortcuts and turns the workplace into a laboratory for rationalizing misconduct.
It’s particularly interesting for people working in listed companies, M&A, investment banking or any environment where insider trading, privileged information and conflicts of interest are live issues. The film remains a very current way to talk about incentives, pressure and the responsibility of those who “know too much” about how the machine really works.
The Wolf of Wall Street (2013)
Directed by Martin Scorsese and starring Leonardo DiCaprio, Jonah Hill and Margot Robbie, The Wolf of Wall Street is based on the memoirs of Jordan Belfort, the broker who narrates his own rise and fall. Grounded in real events, the film follows the transformation of a brokerage firm into a showcase of excess: drugs, conspicuous consumption, client manipulation and open contempt for market rules.
Despite the acerbic, often hilarious tone, the most relevant aspect for executives is how a distorted internal culture gradually normalizes conduct that will eventually be scrutinized by prosecutors, regulators and courts. For boards and senior management, it’s a good starting point to think about how “the way we do things here” shapes decisions that later become evidence.
The Big Short (2015)
The Big Short returns to the 2008 financial crisis from the viewpoint of a few who saw the housing bubble coming before almost everyone else. Directed by Adam McKay and starring Christian Bale, Steve Carell, Ryan Gosling and Brad Pitt, the film is based on Michael Lewis’s non-fiction book The Big Short: Inside the Doomsday Machine.
The narrative alternates dark humor with didactic explanations to show how complex financial products, misaligned incentives and a long intermediation chain can hide systemic risks behind supposedly technical reports.
For those in banking, fintech, securitization, funds or sophisticated credit structures, it’s an invitation to look more critically at what “everyone does” without asking too many questions. The point is not to learn finance from a movie, but to see how decisions taken in small, local contexts – a product approval, a lenient rating, a bonus model – add up to the perfect storm.
Too Big to Fail (2011)
While The Big Short looks at the crisis “from the outside”, Too Big to Fail goes inside the rooms where government officials, regulators and big-bank CEOs made the key decisions during the most acute weeks of 2008. Directed by Curtis Hanson and based on Andrew Ross Sorkin’s non-fiction book of the same name, the film features William Hurt, Paul Giamatti, Billy Crudup, Cynthia Nixon and James Woods, among others.
The camera follows the closed-door meetings where people argue over who gets saved, who fails and what the political and economic costs of each choice might be.
It’s a valuable film for executives who interact with government, depend on licenses and approvals or operate in “systemic” sectors such as infrastructure, energy, health, education or finance. It helps visualize how, in moments of acute crisis, decision-making stops being purely technical, becomes deeply political and often turns into fertile ground for investigations and litigation once the dust settles.
The Intern (2015)
Directed by Nancy Meyers and starring Robert De Niro and Anne Hathaway, with Rene Russo in the cast, The Intern looks like a simple feel-good comedy at first glance. The story follows the meeting between the overstretched founder of a fast-growing fashion e-commerce and a 70-year-old widower who decides to re-enter the workforce as her “senior intern”.
Behind the pleasant tone, the film speaks about governance in young companies, founder burnout, the difficulty of delegating and how this affects the quality of decisions.
For those living the reality of scale-ups, professionalizing family businesses or companies that grew faster than their internal structure, the film offers a gentle – but realistic – mirror on culture, succession, trust and the limits of “I’ll handle everything myself”. It’s not a story about corporate crime, but precisely the sort of context where, if nothing is adjusted, legal problems tend to appear later.
To wrap up the year: movies, downtime and an eye on the company
Streaming catalogs shift constantly, but at the time of writing, in the United States you can find these films on:
– Wall Street (1987)
– available to rent or buy on platforms such as Apple TV, Amazon Video and Vudu/Fandango.
– The Wolf of Wall Street (2013)
– currently streaming on Netflix and also available to rent or buy on Prime Video and Apple TV.
– The Big Short (2015)
– streaming on Paramount+ (including via the Paramount+ channel on Prime), and available for digital purchase on Amazon Video and Apple TV.
– Too Big to Fail (2011)
– streaming on Max (HBO) and also available to rent or buy on Apple TV and Amazon Video.
– The Intern (2015)
– available to rent or buy on Amazon Video, Apple TV and other major digital stores; in some periods it also appears in subscription catalogs such as Netflix or Max.
Always double-check your preferred platform, because availability changes by country and over time.
Beyond that, the proposal is simple: use the holidays to look at corporate crisis away from the boardroom pressure. Watching these stories with the mindset of someone who actually takes decisions – and not just as entertainment – helps sharpen your view of culture, incentives, governance and legal risk.
Pick your platform, block an evening, grab some popcorn and happy holidays!
