5 Must-Watch Sales Movies from the Last 5 Years

5 Must-Watch Sales Movies from the Last 5 Years

5 Must-Watch Sales Movies from the Last 5 Years What movies do salespeople chat about?

Carving out a career in sales is an uphill climb.

You’re expected to work long, unpredictable hours generating new leads; you spend your days calling up prospects who may not be as enthusiastic as you’d like them to be, you get used to bouncing back from rejection, and what’s more, the future of the entire company often relies on you and your team’s ability to close a sale. 

The ups and downs of selling can be extreme: one moment you’re feeling on top of the world, energetic and optimistic. 

Along comes a series of difficult clients and suddenly you’ve hit rock-bottom, feeling like you’ll never close a deal ever again. 

That’s why it’s extremely important for a sales professional to take a break from time to time—to help keep you balanced and ready to handle the challenges of the job.

And what better way to relax than to put your feet up and watch a movie, right?

Salespeople in movies?

Now, Hollywood hasn’t exactly been kind in its portrayal of sales professionals in films. From Death of A Salesman (1985) to Glengarry Glenn Ross (1992) to Tommy Boy (1995), salesmen have either been presented as ruthless sharks, miserable losers or comedic screw-ups

In fact, a study has shown that depictions of salespeople and the sales occupation have been overwhelmingly unflattering or negative, which as perpetuated society’s negative images of the selling profession.

But that doesn’t mean that we should stop watching these films. 

If anything, today’s generation of new sales professionals need to watch these films (no matter how distorted the portrayals seem to be), learn from them and reflect on our own selling practices—what did the characters do right and how can we do better?

Keeping that in mind, go on and sit back, relax and get ready as we list down five of the most relevant (and entertaining) must-watch sales movies released in the past 5 years that you absolutely need to see.

Love and Other Drugs (2010)

What is it about?  

Inspired by Jamie Reidy’s non-fiction book “Hard Sell: The Evolution of a Viagra Salesman”, this rom-com movie stars Jake Gyllenhaal as Jamie, a charming, but slightly shady, electronics salesman forced to switch careers and become a big pharma sales rep after a workplace indiscretion gets him fired. He meets Maggie (played by Anne Hathaway), a girl with early-stage Parkinson’s disease, with whom he soon gets romantically involved.

While the movie mainly focuses on the love story between the two characters, there is a subplot involving the less-than-ideal sales techniques used by pharmaceutical companies to sell their products. Jamie’s character is also a study on how a likeable personality, refusal to take “no” for an answer and persistence to close the sale can often serve you well in the cutthroat world of sales.

Key sales takeaways?

When doing sales it pays to be charming and persistent. People buy from other people that trust, so do your best to build rapport. From the opening sequence of the film, we can see how Jamie charms and relentlessly pursues his customers (from little old ladies, kids, and young women) to get them to buy electronics that they hardly even need. 

And even though we see how dubious and shady the pharmaceutical company really is, Jamie gets his customers to trust him enough to close multiple deals, from convincing them to switch to Zoloft up to successfully marketing Viagra.

The Social Network (2010)

What is it about?

Another film based on a book, The Social Network was based on Ben Mezrich’s The Accidental Billionaires: The Founding of Facebook, A Tale of Sex, Money, Genius, and Betrayal” and tells the story of how today’s biggest social networking site Facebook, came to be. The film shows how Facebook co-founder Mark Zuckenberg (played by Jesse Eisenberg) and his friends Eduardo Saverin and Sean Parker first came up with the idea of setting up a social networking site, and how this idea soon evolved into something bigger than the trio ever dreamed it could be. 

True to its tagline “You don’t get to 500 million friends without making a few enemies”, the film also shows how the trio’s friendship deteriorated, eventually resulting in a couple of lawsuits and million-dollar settlements among the three.

Key sales takeaways?

While this may not seem like a sales movie at first glance, The Social Network actually contains quite a few valuable insights all sales professionals could learn from. Number one is the importance of knowing and giving your customers what they want. As soon as you’re able to do this, your customers will become your best advertisers, as word-of-mouth referrals continue to boost up your credibility and your brand. 

Looking at the movie, we can see how Mark Zuckenberg successfully figured out what his target customers (in his case, Ivy League college kids) wanted—a site where they can share their thoughts and their daily routines with a group of selected friends. Afterwards, we can see how Facebook gained popularity primarily through word-of-mouth testimonials from satisfied users.

Moneyball (2011)

What is it about?

Based on a true story, Moneyball tells the story of Oakland Athletics general manager Billy Beane (played by Brad Pitt) who is devastated over his team’s loss to the New York Yankees in the 2001 postseason games. In an effort to improve his team’s dismal performance, Beane decides to go to Peter Brand (played by Jonah Hill), a young Yale economics graduate who developed an innovative sabermetric approach to analyzing player performance and value. 

Despite initial reluctance from their colleagues and unimpeded by their limited budget, Beane and Brand go on to build a highly-competitive team made up of some unorthodox players. They eventually go on to win 20 consecutive games, thereby setting a new American League record.

Key sales takeaways? 

More than anything, this movie highlights the importance of developing and systematically tracking key performance indicators, both for sports and sales. In the same way that analytics helped Beane develop a winning team, data-driven management techniques and correct analytics can also help sales executives track performance and boost productivity among their sales reps. 

This film may not be necessarily about ‘selling’ but it’s a great look at what can be done when the numbers are right. Remember, sales are all about the numbers. 

Peter Brand said it best when he declared that

It’s about getting things down to one number. Using stats to reread them, we’ll find the value of players that nobody else can see. People are over looked for a variety of biased reasons and perceived flaws. Age, appearance, personality. Bill James and mathematics cuts straight through that.

The Wolf of Wall Street (2013)

What is it about?

Of course, any list about contemporary sales movies would be incomplete without this one. The Wolf of Wall Street, directed by acclaimed filmmaker Martin Scorsese and starring Leonardo di Caprio as shady stockbroker Jordan Belfort, remains as one of the most well-known (and controversial) movies about the sales profession. 

Again based on a true story, this movie details the giddying rise and eventual fall of Belfort, from being one of the most successful stockbrokers in Wall Street to becoming a social pariah whose corruption and fraud were relentlessly exposed. The movie also gives us a glimpse of the glamorous lifestyles led by the biggest names on Wall Street.

Key sales takeaways? 

Looking past the booze and bacchanalia, this movie actually has several key sales lessons that every sales professional can benefit from such as:

Creating a need: One of the most compelling scenes from the movie is when Jordan gets his friend Brad to sell him a pen. The dialogue below is one that all newbie salesperson should take notes from, specifically on how Brad effectively sold his product by focusing on responding to the needs of his customer, instead of simply highlighting the features and benefits of owning a pen—

Jordan (DiCaprio): “Brad, show ‘em how it’s done. Sell me that pen.”

Brad: “Why don’t you do me a favor and write your name down on that napkin for me.”

Jordan: “I don’t have a pen.”

Brad: “Exactly! Supply and demand my friend!”

The importance of sales training: Despite his over-the-top lifestyle, it’s clear that Jordan Belfort was an excellent trainer and motivator. He knew how to pick the right people, and rightly invested in training them to become excellent stockbrokers. He also offered enticing rewards that pushed his people to do better—note that this competitive spirit and drive is something that needs to be honed and developed in all sales teams.

Jobs (2013)

What is it about?

Directed by Joshua Michael Stern, Jobs essentially tells “the story of Steve Jobs’ ascension from college dropout into one of the most revered creative entrepreneurs of the 20th century.” Starring Ashton Kutcher as Steve Jobs, with Josh Gad as Apple Computer’s (now Apple Inc.) co-founder Steve Wozniak, Jobs focuses primarily on 1973 – 2000: Apple’s early years, its founding, and the up and down years of the company, ending with the introduction of the iPod in 2001.

Key sales takeaways? 

While the film has been criticized for several historical inaccuracies, it still shows us a measure of the genius that was Steve Jobs. The movie’s tagline “Some see what’s possible, others change what’s possible” accurately conveys the spirit of innovation that Steve Jobs lent to the company—and this willingness to embrace change is something that all sales professionals should learn. 

From using technology to generate leads up to closing deals and tracking productivity, sales people should be frontrunners of innovation. Comparing Jobs to the canonical film A Death of a Salesman, we can see that while Willy Loman failed because of his inability to adapt to change, Steve Jobs became wildly successful because he embodied change.

Haven’t seen these must-watch sales movies yet?

So, do yourself a favor.

Grab a teammate or two, and choose from this list of movies—if you haven’t watched these already!

Already watched some of these— or all?

Share your takeaways in the comments!

FREE EBOOK: 21 Tips Seasoned Sales Reps Won't Tell You

Prospect better.
Sell smarter. Close more.

  • The tips include:
  • Recognizing buying cues
  • How to handle follow up calls
  • Working on your speaking voice
The following two tabs change content below.

Patrick Hogan

Patrick is a Co-Founder & Chief Executive Officer of Tenfold.