5 Must-Watch Sales Films

5 Must-Watch Sales Films

Rhema Hans
Rhema Hans
Table of Contents
Table of Contents

From good guys to bad guys, characters in movies tell us a lot about what it takes to succeed in business. Who knew a character like Irv from Cool Runnings could have valuable insight to impart about succeeding in sales. Or the character of Gordon Gekko from Wall street: Money Never Sleeps would teach us how time is a critical factor in making sales.

Movies are more than just a source of entertainment today. There are life lessons and business lessons in films that can go a long way in your journey in the real world.

You know what your problem is, it's that you haven't seen enough movies - all of life's riddles are answered in the movies.- Steve Martin

With the same belief in mind, in this article, we have enlisted 5 legendary sales films that can help you both as a business owner and a salesman. So, let’s get started!

The Wolf of Wall Street

Hard work beats talent. Every time!" - Jordan Belfort
The Wolf of Wall Street

The Wolf of Wall Street is the story of the rise and fall of a stockbroker Jordan Belfort played by actor Leonardo DiCaprio. The start with, the movie is not for everyone but for you if you are a salesperson or you run a sales team. Or you aspire to become a salesperson.

In the film, the striking point is how Belfort was incredibly determined to make the sale. No matter what. He never hung up the call until the deal was closed.

The film or the character of Belfort portrays the importance of building rapport with the customer right away to gain their trust, to make a sale. It also shows that no matter what, you must continue selling. Your opening of the sales pitch and closing should  be as if it’s the only chance to sell your product/service.

Another key takeaway from the film would be, how to run a sales team. Belfort had two meetings a day, shared inspirational messages and also offered incentives to top salespersons on a regular basis. As a sales manager, you might not be able to get DiCaprio’s character right in your life, but you can set monthly goals, offer prizes to the top sellers and motivate your team. Here are 30 motivational sales quotes you can share with your team.

Belfort’s sales strategy were on point and they were not just limited to his customer. The starting point of his sales strategy was to train his employees. Belfort transformed uneducated and unqualified people into selling machines. Making it a win win for both the company and the employees. Your another takeaway from this is to hire the right people not necessarily the most experienced but nurture them to ensure they are successful.

Lastly, the film encourages you to have a never say die attitude. After Belfort lost his job on Wall Street when his firm crashed, he took a job selling meaningless penny stocks. He didn’t get discouraged. He rather used his competitive nature, knack for selling to pick up the phone and make the sales calls.

Jordan has never-ending confidence in himself and becomes completely egotistical thinking that he's unstoppable. Everyone could probably relate to wanting to be confident in themselves, but maybe not to the extent that Jordan is.

Boiler Room

“There’s no such thing as a no-sale call. A sale is made on every call you make. Either you sell the client some stock or he sells you a reason he can’t. Either way, a sale is made. The only question is, who is going to close? You or him?”
Boiler Room

Cold calling is the ultimate in selling. It involves you giving your all to someone you've never spoken to. Avid practitioners of cold calling often refer to the aggressive tactic as an extreme sport. And this is what the film Boiler Room is all about.

A college dropout, attempting to live up to his father’s high standards, gets a job as a broker for a suburban investment firm which puts him on the fast track to success.

Boiler Room starring Giovanni Ribisi and Vin Diese, is inspired by the story of David Glass, a former stockbroker whose experience cold calling for a brokerage gave a sales lesson to many.

When Vin Diesel’s character takes over a call to close a deal for a junior representative we understand what a hard sales pitch means. It may not be the most legitimate of sales but it sure is effective.

The character of Vin Diesel verbally pushes his client into a sale stating that he simply hasn’t got the time to help. This is a master albeit ruthless salesman at work displaying many hard sale techniques executed with precision.

In one of the scenes in the film, a typical cold-call begins with a decision maker who is too busy and concerned with their immediate problems. They will not want to pay any attention to you or your solution.

As a sales rep, you should prepare for this disposition and create a script that helps you keep their immediate attention. Hence, Ben’s “Hey tell me something, now you’re a doctor.” as a conversation starter completely transforms the call. It humanizes Seth as a normal person attempting to have a conversation instead of pursuing a goal. It attracts the attention of the decision maker to discuss the sale in a context that is familiar to the doctor.

The main takeaway of the Boiler Room is that Sales principles and persuasive techniques are essential to building a successful sales portfolio. But to build a successful and sustainable business, you must make clear distinctions between persuasion and manipulation.

“DON’T PITCH TO WOOD" was their terminology for the most realistic sales point made in the movie, meaning that the reps shouldn’t spend time with people who can’t or won’t make a decision.

A few tips from the film would be:

  • Believe in the product you're selling
  • Research
  • Deliver your pitch concisely
  • Remove “no” from your customer’s options
  • Make sure to follow up with your customers


“Hard work may not always result in success but it will never result in regret” — Moneyball

Moneyball is a 2011 American biographical film directed by Bennett Miller. It is based on the 2003 nonfiction book by Michael Lewis. The story is focused on solving one problem, getting the best trade-off against a precise outcome. In this case, get the most wins with the least money- Return on Investment. It is a film every sales team must watch.

You first takeaway from the film is, A series of calculated steps showed that wins were driven not by batting average, but on-base and slugging percentage. How did they discover that? Set the outcome first and then run “simulations” of various predictors until one comes the closest.

For sales managers, if exceeding quota is the desired outcome, then run several individual and combination factors of sales rep behavior until you find one that is the closest predictor.  

A baseball team needs to be consistent in all areas and address critical gaps. What a gripping episode when the A’s, desperately wanting to replace Giambi, get into a bidding war for Hatteberg so they play him in first base, just for his on-base performance.

Similarly, a customer-facing team consists of inside reps, field sales, specialists, customer service agents and operational personnel. A good service rep cannot by themselves undo poor touch points delivered by other members of the team. Even among the sales reps, consider the strengths of each rep and deploy them where the team needs improvement or a certain performance needs to be met.

For example, if a certain sales rep has strong knowledge and success in a particular product category, deploy that rep with a customer base where you need to achieve critical success in this category.

While all the traditional indicators are valuable and have a role in running your team, the lesson from Moneyball is that we must look beyond the obvious, to dig deeper into what most people can’t see.

Believe that you can win over larger competitors with deep pockets by deploying a thoughtful and cohesive analytic approach. In the end, in Moneyball it mattered less how much money the Oakland A’s spent than how well they spent it. Similarly, it’s about the quality of one-on-one sales conversations, not the quantity of sales calls.

Pursuit of Happyness

Walk that walk and go forward all the time. Don’t just talk that talk, walk it and go forward. Also, the walk didn’t have to be long strides; baby steps counted too. Go forward
The Pursuit of Happyness

2006 biographical film The Pursuit of Happyness, yes that's how "Happiness" is spelled in the film, that starred Will Smith as a homeless salesman trying to make it in life, perfectly showcases some of the best aspects of a “good salesman.”

The struggles of Will Smith in the film as a common man was perhaps not relatable for everyone, but Will Smith’s character as a salesman was certainly relatable to most of the salesmen.

The optimism that Smith shows about his sales, is the main lesson to learn for the salesmen today. Smith remains optimistic, even though he’s under the realization that no matter how hard he works he still can’t get the number of sales calls that he makes.

Very often we encounter sales persons who’re angry or bored or frustrated and as customers it immediately turns us off; but here is a man who even through countless hours of frustrated efforts still maintains the positive, cheerful optimism that in the end lands him the sales opportunity.

Salesmanship might just seem as a monotonous, hectic, job, however, thinking creatively might just change that. This is not what we are saying, but exactly what we learn from Will Smith’s character in the film- Thinking creatively even as a salesman.

While making the sales calls he realizes calling his way up the list seems to be a dead end, he opts to call the highest person on the list; and because he thought differently he ends up landing a much better sale than what he may have ended up with had he not.

Even for us in the sales world, this means sometimes we must be prepared to go against the norm, even our own comfort zones, and try something that may seem crazy to us.

We also see that as a salesman, Smith was very flexible. He was very much willing to be flexible with the client he has on the phone. As sales persons we often have to put aside our own pride and choose to satisfy the needs of our customers first. He realizes the importance of this client, given that he is at the top of the list, and seizes the opportunity by making time to help the client.

Chris Gardner's partner thinks that his idea of entering the stock broking field is too high aimed and absurd. Did it affect Chris's goals? No! Do the same while you are moving ahead on your journey of success. Listen to other people, but do not let it affect or influence your actions and decisions. This is a lesson for you both as a salesperson and a common man.

Death of a Salesman

When today fails to offer the justification for hope, tomorrow becomes the only grail worth pursuing.
Death of a Salesman

This one is an important one in the list of the sales films. Arthur Miller's 1949 film Death of a Salesman is about what happens when a salesman, Willy Loman, fails to accept the changes happening within himself and the society around him.

The titular salesman who is 63 years old and unstable, insecure, and self-deluded. He vacillates between different eras of his life throughout the play, and re-imagines them as if they were real. Willy's age and degrading mental state has him appear childlike and reliant on others for support, coupled with his recurring flashbacks to various moments of his life.

His first name, Willy, reflects this childlike aspect as well as sounding like the question "Will he?" His last name gives the feel of Willy's being a "low man", someone who will not succeed; however, this popular interpretation of his last name was dismissed by Miller. A self-centered man who fails to appreciate his wife, he also suffers from an inability to acknowledge his own limited success.

The film demonstrates how a person’s self-perpetual denial can impact those around him, and include them. Today, many men and women in sales are avoiding the mirror, believing, like Willy, that their inability to achieve their ideal of financial success is somehow a reflection of their own self worth. In order to learn from Miller’s play and avoid Willy’s fate.

What you learn from the film is that, don’t delve so deeply into your work that you have a sales burnout. Here are the signs of a sales burnout.


Feeling tired all the time emotionally, mentally or physically and not having any energy, of being completely spent.

Lack of Motivation:

Not feeling enthusiastic about anything anymore or lacking internal motivation. It may be harder to get started in the morning, and it may feel like you have to drag yourself to work.


You may feel disillusioned and fighting the feeling that your work doesn’t matter. You might be more pessimistic than usual about your work and your contributions.

Not Taking Care of Yourself:

Drinking or smoking too much, being sedentary for long periods of time, poor eating habits be it eating too little or eating too much junk food. Or lack of sleep.

Interpersonal Problems at Home and at Work:

Having more conflicts with other people, such as getting into arguments; or withdrawing, talking to coworkers and family members less. You’re there physically but not mentally.

If you find yourself having a sales burnout then here are a few ways to beat

Relaxation Techniques:

Easier said than done, but it is important for you and your family. Relaxation techniques like meditation, listening to music, reading a book, taking a walk, or visiting with friends and family designate time for it.

A Rich Non-Work Life:

Find something outside of work to be passionate about that's challenging and engaging—i.e., a hobby, sport, fitness activities, volunteering in the community.


Don't let work stress seep into family and vacation time. Set boundaries by turning off cell phones at dinner and delegating certain times to check email.

Get Enough Sleep:

Research suggests that having fewer than six hours of sleep per night is a major risk factor for burnout poor sleep can have negative effects on job performance and productivity. It can lead to fatigue, decreased motivation, impaired mental function.

In Willy Loman, Arthur Miller gives the audience and certainly today’s salespeople someone with whom they can relate. This is someone who fears being left behind in the rapidly changing times.

So, today’s salespeople should heed Miller’s warning, take care of themselves, remain in step with the times and in tune with others. Avoid tragedy, and sales burnout, and enjoy prosperity instead.

How Deskera Can Assist You?

These 5 movies for salespeople listed above certainly have a lot you can learn from as a salesman or a business owner. Along with that, a right software can only make your sales life better. A software that can not only help you with sales, but can do everything your business needs to run successfully, doesn't it sound like Deskera?

Whether you are a sales manager or running your own business, there are tons of duties and responsibilities that you have to fulfill. Using the Deskera CRM+ system, you can manage your contacts, leads and sales deals. You can use the CRM system to manage all customer data and manage your leads and deals.

Here is a quick walkthrough to help you understand how Deskera works:

Deskera will help you to save the time taken in transferring customer data between the different systems. Having a good CRM system will help you manage your financial and sales reports and be prepared to kick-off your meetings.

Deskera can also assist you with real-time updates about your business like cash flow status, customer satisfaction, inventory management, sales, purchases, purchase orders, customer tickets, customer satisfaction, managing leads, revenues, profit, and loss statements, and balance sheets.

Automate Your Sales With Deskera
Manage both sales and support from one single platform.

Moreover, it would also help in integrating sales methodology across different platforms onto one system so that you have a consolidated list for email campaigns, leads management, and sales pipeline to mention a few.

It will also help you to sync between your orders, payments, taxes, refunds, product variants, sending out invoices and reminders, facilitating invoice management, and even undertaking follow-ups and advertisement campaigns.

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