5 Must-Watch Movies For Anyone Working In Sales

Bartosz Majewski in

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What are the all-time great movies for salespeople? It’s hard to find a list online not including “The Wolf of Wall Street” (no worries, it’s not on this list, though!). What I have for you is not only reviews and trailers, but also brief descriptions of what you should pay particular attention to as a salesperson when watching the best films about sales. Here’s an original list of the five best films about business for sales reps.

The best sales movies of all time

Hollywood loves improbable stories. The same goes for other media. Front pages of daily mags always show shocking and appalling news about very unique individuals, who have suffered a terrible tragedy in peculiar circumstances. But should this really surprise us?

There’s this journalistic rule of thumb – you have a hot topic when it’s the dog that’s been bitten by a man, and not the other way round. The silver screen won’t bother with movies about a group of employees who have been working 5 days a week, from 9 to 5, for 45 years, and successfully providing people with a service, thus making their lives slightly better. And that’s only right, as this kind of story isn’t bound to capture the audience (so many years of hard grinding and not a single swing of momentum!).

Why not “The Wolf of Wall Street”?

Hollywood scripts resemble TV news flashes. If you want to learn how to run a business selling stocks, you shouldn’t necessary turn to “The Wolf of Wall Street”. Startups usually don’t look like a part of the “Social Network” or “Silicon Valley” screenplay either. Business flicks aren’t guides to making sales, but rather inspiring stories with business playing second fiddle, not aspiring to educate anyone.

Although most blockbusters aren’t a ready recipe for success, the ones I chose will surely inspire you. Every entry also includes a short description and some tips regarding which of the presented selling methods are worth paying attention to.

Here’s a list of the most interesting movies for salespeople:


In 2008, global financial markets were hit by a crisis, which 9 years later has been all but forgotten. Only a handful of people predicting a looming catastrophy want to get rich using their knowledge. They bet on an event which was unthinkable and wasn’t expected by anyone.

Why watch it?

To appreciate the excellent characters including Ryan Gosling. Especially in the scene where he uses Jenga to explain to customers why they should buy the product he pitches.
For great storytelling/direction work. If you’ve never bought stock or trust funds, you’ll have a hard time understanding what this story is about. The director has approached the issue in a masterful and humorous way. By employing celebrities to explain complicated financial terminology, he’s laid out the mechanism behind the industry juggernauts in layman’s terms.

Need an example?

  • Selena Gomez in a tight black dress, playing blackjack at the casino explains what synthetic collaterialized debt obligations are.
  • Margot Robbie, laying naked in a bubble bath, breaks down mortgage-backed securities.
  • Anthony Bourdain, the American chef, talks about how banks build up toxic assets in CDO using a restaurant dish to describe the process. The chef chops up pieces of stale fish and serves it as “fish goulash”.

These are just some of the reasons why I feel like you should see the adaptation of Michael Lewis’ book.

This movie is worthy of your time not only because of its realism. McKay proves you can discuss difficult topics in a straightforward manner. Sometimes, I hear from sales reps that I work as a consultant with that they have a tough product, that the customer doesn’t understand. “Big Short” shows plain and simple that they’re wrong. Why? Because regardless of how complicated the product is, you can explain it in simple terms. If it was possible to demonstrate how the forward contract market works the way it was done, then there’s no excuse for any of us for not being able to explain the product to the customer in simple terms.


How an elderly mixer seller has built an empire worth 700 mln dollars? This is a question guaranteed to interest any salesperson. Thanks to persistence – that’s how the trailer for “The Founder” begins. Although the movie covers the story of the most famous fast food chain in the world, it’s no visual fast food at all.

A salesperson approaching retirement travels the US with a trunk full of milkshake machines. One day he comes across the McDonald brothers, who’ve opened up a fast food joint. John Kroc, amazed by the company’s growth pace, offers them to create a network of franchise diners all over the country.

The film is worth watching if only to learn with the main protagonist the lesson about persistence and resilience when facing rejection. Indeed, the main character is ruthless, which helps him accumulate massive wealth. It’s tough to deny him grit and endurance in his quest, as well as business partner selection and adaptation skills.


Ben Affleck throws keys to his Ferrari at candidates during job interviews. He’s 27, a millionaire, and doesn’t mince words when ordering one of the young broker prospects to leave the meeting. He impresses an army of money-hungry twenty-somethings, who wish to become a part of the company and have the opportunity to earn a million dollars within three years. One of the young, future salespeople being recruited is the main character – Seth – who perfects the art of manipulation and joins the tight circle of the company’s top employees.

The film is worth watching and… listening to – first off – because of the brilliant dialogues and scenes of closing deals, which one watches with bated breath. Second – for the scenes referring to communicating company values and the kind of punishment that awaits those, who don’t observe them. Third – here’s a little something for young sales reps – the movie is a great opportunity to see how one was winning clients back in the days when there was no Internet, and a business card was your lead. Finally, for the amazing dialogues. Fun fact is that the movie tells the story of and is based on the same company as “The Wolf of Wall Street”, although there’s a lot less drugs in it.


This is the only piece on this list that the male part of the readers can watch with their wives saying “honey, we’ll watch a romcom tonight”.

The film tells a story of a rich and influential sports agent, who suddenly loses everything and has to change his ways. Why should you watch it if you’re working in sales? Because it’s also a story about courage and persistence. Especially the first half of the movie provides a behind the scenes look at brutal business – on average, an NFL player is looking at a mere 18-month long career. Every year and a half, agents of these athletes need new rookies to work with and steadily close sales to a limited group of clients. If you take a moment to recognize the conditions that Jerry Maguire works under, you’ll be able to learn from him some methods for functioning in a very competitive niche.


This film is like a Greek tragedy and kinda resembles a month of low sales. All prospects say ‘no’, you have no money and things are just not working out for you in general.

As far as “The Founder” was saying you can have lots of luck and reach out for more, “The Pursuit of Happiness” says you can bounce back even if you hit rock bottom. The first lesson you learn? Never invest all you have, even if the product seems genius. Lesson number two – you have to be persistent, not get discouraged, fight with all your might and always get up after a loss, especially when it seems like there’s no way out. Salespeople also have to be tireless, never give up and stay strong even after being turned down time and time again.

Movie nights

Working in sales means constant phone calls and an unending list of emails to write. On top of that you want to grow, so you’re reading tons of books and tens of sales blogs. I suppose it’s not easy for you to find time for entertainment, but sometimes you just need to unwind. The strategy I put forward will allow you to combine business and pleasure. Each of the movies I suggested is a valuable lesson in sales. You can start planning your movie nights and spend them with your partner while having some fun and learning new things at the same time.

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Bartosz Majewski

Co-founder of RightHello. Ten years of experience in sales. Has executed business expansion into 38 markets on 6 continents. A regular speaker at business conferences. An active snowboarder outside of work. Avid book reader and blogger.