9 Movies Every Salesperson Needs to Watch

March 20, 2019

Best Sales Movies

Editor's Note: As we start the second half of 2019, we're looking back at some of the year's most popular posts on the LinkedIn Sales Blog. This one ranked No. 2.

The scent of popcorn wafts through the living room. Assorted candies and snacks are spread out across the coffee table. You’ve loaded the sofa up with blankets and pillows for maximum comfort.

Is there anything better than movie night?

I can think of one thing that upgrades the experience: When those movies you settle in to enjoy offer value beyond mere entertainment. I would guess I’m not alone in saying I’ve watched plenty of flicks that had a lasting impact on me.  

In particular, I like watching stories that help me grow professionally, by providing me with perspective, applicable lessons, or simply inspiration.

These 9 films, in my opinion, all have something to offer for today’s sales pros. They cover a vast assortment of genres and time periods and subject matter, but at the end of the day, these are all movies about sales, one way or another.

9 Movies About Sales You Should Watch

Death of a Salesman

Based on the classic play by Arthur Miller, this movie was made for the small screen (it premiered on CBS in August of 1985) but offered Hollywood-caliber drama and performances (from Dustin Hoffman and John Malkovich, among others.)

As its name suggests, Death of a Salesman is not the most uplifting of affairs — its protagonist is a failed traveling salesman whose life more or less falls apart — but ultimately there are good takeaways here about setting realistic goals, and accepting ourselves for who we really are.

Money Quote: “Walk in with a big laugh. Don't look worried. Start off with a couple of your good stories to lighten things up. It's not what you say, it's how you say it, because personality always wins the day.” — Willy Loman

Glengarry Glen Ross

The early scene in which Blake, an arrogant hotshot sent from downtown to motivate a lagging collection of real estate salesmen, arrives and verbally berates the embattled team is unforgettable. Alec Baldwin’s vitriolic, profanity-laced takedown is riveting, hilarious, and heartbreaking all the same time. “Put that coffee down! Coffee’s for closers!” he barks at Shelley Levene (Jack Lemmon) as he meekly tries to pour a mug.

Levene is one of the classic salesman archetypes in cinema, personifying the pressure and rejection that can be incumbent to the profession. (The character became something of a pop-culture stereotype in and of itself.) The movie is a fun throwback to a bygone era, with salesmen dialing up prospects from phone booths and desperately yearning for that coveted stack of Glengarry leads. (If only they had Sales Navigator to generate their own!)

Money Quote: “A-B-C. A: Always, B: Be, C: Closing. Always be closing.” — Blake

The Big Kahuna

Most B2B salespeople know about the thrill of chasing that huge, game-changing deal. The one that makes your month, or even your year. That’s the focus here, with the titular “Big Kahuna” being the CEO of a large company who is targeted by a trio of industrial lubricant sales/marketing reps at a trade show.

The interplay between these three characters, and the many reflective moments, make this comedy a worthwhile view even beyond the laughs.

Money Quote: “It doesn't matter whether you're selling Jesus or Buddha or civil rights or 'How to Make Money in Real Estate With No Money Down.' That doesn't make you a human being; it makes you a marketing rep. If you want to talk to somebody honestly, as a human being, ask him about his kids. Find out what his dreams are — just to find out, for no other reason. Because as soon as you lay your hands on a conversation to steer it, it's not a conversation anymore; it's a pitch. And you're not a human being; you're a marketing rep." — Phil Cooper

The Pursuit of Happiness

A career in sales can be a struggle, requiring us to look deep within ourselves. No film epitomizes this truth better than The Pursuit of Happiness, in which Will Smith plays a medical equipment salesman named Chris Gardner who finds himself homeless after a run of bad luck. He tries to dig his way out of destitution and provide a better life for his son.

Gardner’s sad plight turns into an uplifting resurgence as he employs a variety of savvy sales tactics during an unpaid internship at a brokerage firm, focusing on the highest-value prospects and relying on his strong interpersonal skills. Through impressive performance, he earns a paying job and eventually starts his own successful company. I dare you to watch this film and not feel utterly inspired.

Money Quote: “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.” — Chris Gardner

The Wolf of Wall Street

Here we have the flip side of the coin. Leonardo DiCaprio’s Jordan Belfort rises from humble beginnings to Wall Street kingpin thanks to his ability to execute (and teach) the hard sell. Once he gets on the phone, his persuasive abilities are divine as he convincingly paints worthless stocks as can’t-miss opportunities.

Belfort quickly climbs the ladder as he builds his company Stratton Oakmont into a powerhouse, all while he spirals out of control amidst drugs and debauchery, and things eventually unravel in rather spectacular fashion.

Money Quote: “The only thing standing between you and your goal is the [BS] story you keep telling yourself as to why you can't achieve it.” — Jordan Belfort

Boiler Room

Like Wolf of Wall Street, Boiler Room depicts aggressive brokers peddling junk stocks with inflated promises in search of hefty commissions, albeit in a very different style. Compared to most other movies listed here, this one takes a somewhat more serious look at the impact and consequences of dishonest sales tactics.

Money Quote: “There is 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 gonna close? You or him?” — Jim Young

Jerry Maguire

After dramatically breaking off from his sports agency to go it alone, Maguire (played by Tom Cruise) has to sell himself to clients to remain viable. The decision that sent him down this path is one that resonates in today’s digital sales world: quality over quantity. He wanted to work with fewer clients in order to deliver better and more personal service.

Ultimately, Maguire is only able to convince one client to stay with him at his new solo venture, but the strong relationship he builds with Rod Tidwell (Cuba Gooding Jr.) eventually gets noticed by others, opening new opportunities and saving his career.

Money Quote: “The key to this business is personal relationships.” — Dicky Fox

Moneyball

Sticking in the sports realm, we come to the story of Billy Beane (Brad Pitt), who transformed the way baseball front offices operate with his innovative approach as Oakland A’s general manager back in the early 2000s. This film (based on a book of the same name) shows how Beane built a small-market contender by identifying and capitalizing on market inefficiencies. In this case, his data-driven approach points him toward on-base percentage as an undervalued asset.

You are (probably) not in the business of constructing an MLB roster, but the takeaway for sellers is this: What’s your market inefficiency? Where is the untapped opportunity in your space that competing salespeople are overlooking?

Beane’s attempts to sway traditional mindsets in the organization toward a new, unfamiliar way of thinking might help inspire any sales pro who faces a firmly established status quo.

Money Quote: “We are card counters at the blackjack table. And we're gonna turn the odds on the casino.” — Billy Beane

A Christmas Story

Okay, this one’s a little outside the box. You won’t find this cherished holiday staple on many “Best Sales Movie” lists, because it’s not about sales in any way. Or is it?

Throughout the entire movie, young Raphie is trying to sell his parents on the Red Ryder Carbine Action 200-shot Range Model air rifle that he so desires, playing up the benefits (a compass in the stock, and this thing that tells time) while downplaying the widespread objections (one is liable to shoot his eye out). Eventually his resolve wins out.

It’s an epic tale of tenacity and persistence.

Money Quote: “It was a classic, mother BB-gun block. ‘You'll shoot your eye out!’ That deadly phrase, honored many times by hundreds of mothers, was not surmountable by any means known to Kid-dom, but such was my mania, my desire for a Red Ryder carbine, that I immediately began to rebuild the dike.” — Ralphie Parker

Watch and Learn

Not all of these movies cast the sales profession in the best light. Few of them tie directly to the work we do today of engaging prospects and building relationships in the digital space. But as you watch these heralded classics, you’re bound to come away with some insight and food for thought.

At the very least, you’ll have a stomach full of popcorn and candy. Now there’s an easy sell.

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