The 5 Best Sales Movies to Learn From

At the end of the day, there are few things I like to do as much as grab some popcorn and put on a movie. If that’s what you like to do and you want to step up your sales game, there are plenty of great movies about sales to add to your watchlist. 

Hollywood’s idea of salespeople may often be the stereotypical image of a degenerate who’ll say anything to close the sale, no matter how unethical. But there are still positive portrayals of the sales profession to be seen. In either case, whether they’re the good guys, the bad guys, or something in between, our pick of sales movies is sure to entertain, and maybe even leave you with a few lessons you can use in your sales. 

So, if you want your next Netflix binge to be more productive, here are some of our favorite sales movies. 

It’s impossible to talk about sales movies without mentioning Glengarry Glen Ross. Probably the most well-known movies about sales, the plot follows an office of real estate salesmen. At the end of the week, the top salesman will get a Cadillac. Second place gets a set of steak knives. Third place gets fired. 

Although he only appears in one scene, Alec Baldwin and his “motivational” speech steal the show. In just a few minutes, we learn that coffee is for closers (which could be bad news for me, as I don’t begin to function until I’ve had at least two cups), the ABC of sales (Always Be Closing), and the AIDA framework: Attention, Interest, Decision, Action. 

There are plenty of other lessons for salespeople. While I sincerely hope that your office is nothing like this, the movie does portray sales as hard work and loaded with pressure. It also shows what happens when the manager is seen as a hindrance, rather than a support. 

But the main takeaway from this film is the importance of good leads. In the movie, the “Glengarry leads” have an almost mythical status, something that some of the salesmen will do anything to get their hands on. These are the best, most lucrative leads, worth thousands of dollars. 

The value of a good, qualified lead cannot be overstated. Fortunately, we’re not reliant on some mysterious figure to hand us promising leads. Whether it’s through inbound sales or searching for leads on LinkedIn, it’s now much easier to find good leads, the ones looking for a product/service just like yours. No breaking into offices required!

For a more feel-good film, you can’t go wrong with The Pursuit of Happiness. Based on a true story, the movie follows Chris (Will Smith) as a struggling salesman who faces incredible odds. After his wife leaves him and he ends up without a home, Chris must look after his son while trying to secure their future. When the opportunity for an unpaid internship at a stockbroker comes up, Chris puts in the hard work to get a better life for him and his kid. 

Next time you feel like the odds are stacked against you, take a page out of Chris’s book. In incredibly challenging circumstances, he maintains a positive attitude, especially in his interactions with others. Rather than blaming others or becoming bitter, staying confident will come across in your sales. 

But what impressed me even more than Chris’s attitude was his ability to work smarter, not harder. With his obligations to his son, he must accomplish more than the other interns in less time if he’s going to stand a chance of getting the job. For him, that meant not hanging up the phone between calls or changing the order of the calls in the list he went through. 

The good news is that you don’t have to go to the same lengths to save time. For example, auto dialers can save you even more time. Email automation means you can scale up your outreach while keeping it personal. Analytics can help you see what’s working and what isn’t. Using the right sales automation tools lets you focus on higher value tasks and sell more. 

The Wolf of Wall Street

© Universal Pictures

“Pick up the phone and start dialing! I want you to deal with your problems by becoming rich!” 

Another film based on the true story of Jordan Belfort, this couldn’t be more different from The Pursuit of Happyness. Jordan rises to conquer Wall Street while doing obscene amounts of drugs and defrauding investors, before eventually spending 22 months in prison when the FBI caught up with him. It’s impossible to hold up Belfort’s actions as anything other than immoral. Leonardo DiCaprio plays the part with incredible energy and charisma. Top performances by Jonah Hill and Margot Robbie also helped secure plenty praise and awards for the movie. 

While I wouldn’t recommend following Belfort’s example (I’m going to go ahead and say that cocaine and hookers are not actually the key to success in sales), the way Belfort sold is poetry in motion. He wasn’t just selling stocks. He sold the dream. He painted a picture of what their future could look like with mortgages paid off and money in the bank.  

The movie also features the best response I’ve heard to the famous “sell me a pen” interview question. Rather than trying to explain the pen’s features, the character Brad simply asks Jordan to write his name on a napkin. Jordan responds that he doesn’t have a pen. And 

Brad counters with “Exactly. Supply and demand, my friend.”

When you’re selling, don’t get caught up on the features. Instead, show clearly how your product or service can make life easier and help your customers with the jobs they must do.

Just do it with more integrity and fewer drugs, okay?

Want to learn more about how to sell like the real Wolf of Wall Street? Check out “Way of the Wolf,” one of our top recommended sales books, for a refreshingly ethical approach to selling.

Time for something with a little more romance. Jerry Maguire is a successful sports agent. But after one of his clients is injured and Jerry’s accused of not having the client’s best interests at heart, he has an epiphany that leads him to believing that he should care more for his clients. Unfortunately, this idea isn’t popular with his superiors—surprisingly, “fewer clients and less money” didn’t go down as well as you might think. ґ

While many people remember Jerry Maguire for the famous “show me the money” scene or 

Renée Zellweger’s “You had me at hello,” there’s a lot that salespeople can take from the movie. Jerry finds true success when he starts being genuinely invested in his clients, by caring about them and being committed to helping them get the best outcome possible. 

Unlike the Glengarry Glen Ross mantra of Always Be Closing, Jerry is more focused on the clients and sees them as people, not numbers. In this way, Jerry is the personification of relationship selling. By building a connection with your customers and helping them achieve their goals, you will build stronger relationships and greater trust, an essential for today’s salespeople. 

Who doesn’t like a good singalong? We finish off our list of sales movies with one of the more popular musicals in recent years. The story of the legendary (and controversial) showman P. T. Barnum, The Greatest Showman, is about the start of show business. While I’m not encouraging you to sing your next pitch, Barnum’s ability to capture the imagination of his audience is a great skill for any salesperson. 

When his first attempts at selling tickets to the Barnum Museum meet limited success, his daughters point out that he needs something “sensational.” Likewise, a successful salesperson needs to know what’s sensational about their product/service. What makes it different from your competitors’ solutions? What is your Unique Selling Point (USP)? 

Once you’ve found what’s special about your product, you must explain it in a way that grabs your prospect’s attention while clearly conveying the benefits. For example, you could include a personalized image in your outreach email, or embed a video that highlights precisely how your product could help your prospect. 

Final thoughts

It’s great to put your feet up and enjoy a good movie, but it’s even better if that movie can help you improve your sales skills. Whether they’re good or bad, there’s plenty we can learn from Hollywood’s version of salespeople, while being entertained at the same time. So, next time you have a well-deserved break, put one of these classics on.

Let us know what your favorite movie about sales is in the comments below! Then, when you’re ready to put your new sales skills to work, try out Reply with our free 14-day trial.