There’s no shortage of movies about sales. Some make the profession seem like a glitzy, high-roller gig with boozy client lunches and evenings filled with bottle service and beautiful people. Others paint salespeople as sleazy grifters, one step removed from carnival hucksters out to relieve honest folk of their hard-earned money. And while we all know that reality is (usually) different, there’s still a lot of wisdom to glean from some of the best sales flicks out there.
From motivational speeches that get you fired up to hit your quota to cautionary tales filled with bad behavior and unethical tactics, we ranked the best sales movies of all time and broke down what you can learn from each of them.
Apply these lessons to your own sales technique using our new tech buyer research on the four selling skills that break and make deals:
5. “Boiler Room” and “The Wolf of Wall Street”
Yes, we’re cheating right off the bat by giving both these flicks the fifth-best spot. That’s because they’re both based on the life of legendary penny stock pitch man Jordan Belfort. Belfort’s Quaalude-addled parties and high-pressure sales style made for terrific source material, and both these pictures portray the highs and lows of a selling style with high stakes and no morals.
What you can learn: While we wouldn’t suggest anyone view these movies as how-tos for getting ahead in the sales game, both show just how far a great sales script and a polished pitch can get you. The salespeople in these films know how to connect with their prospects because they know what makes them tick. The best sellers know how to drive conversations that create excitement. Both these flicks will get you fired up.
4. “Salesman”
This seminal 1969 film by noted documentarians Albert and David Maysles follows a group of traveling Bible salesmen slinging the good word in a variety of low-income neighborhoods around the U.S. The sellers in question speed, swear, and pitch their way through the film while trying, sometimes in vain, to make their quotas. It’s a movie that many haven’t seen, and that’s a shame, because it’s as terrific as it is heartbreaking.
What you can learn: In almost diametrical opposition to the two films based on Belfort above, “Salesman” doesn’t make the sales role seem glamorous at all. In fact, it’s very much the opposite—especially because the main character in the documentary is a man who continually struggles to make quota. That’s something every seller’s dealt with at some point in his or her career, and the doc makes a great case for getting creative and not giving up, even when the chips are down. It also shows that using the same pitch over and over again, without getting to know your prospects and their motivations, is a recipe for disaster. Take stock of your calls, decks and emails, do they all look the same? Or are you >configuring your messaging in a way that gets attention?
3. “Death of a Salesman”
Arthur Miller’s Pulitzer-winning play has been adapted for the big screen a number of times, perhaps most notably in 1951 by László Benedek and again in 1985 by Volker Schlöndorff (no, we didn’t make up either of those names). It’s a tale of delusion, despair, and the death of the American Dream. You probably read it in high school, but you should see the silver screen version, too.
What you can learn: Protagonist Willy Lohman seems like a luckless schmuck—until you realize that all his problems are of his own making. He indulges in fantasies about success and refuses to change, even though he’s both woefully unsuccessful and driving his family away. It’s a cautionary tale about a seller who can’t change his ways, despite the fact that he continues to fail monumentally. There’s a lot to take away from this film, but the key selling lesson is clear: adapt or die. What’s the modern equivalent? Product selling. Today’s best sellers use insights, not demos to sell. Sticking with outdated approaches leads to failure.
2. “Vacuuming Completely Nude in Paradise”
Danny Boyle’s criminally underrated 2001 film follows the travails Pete, a young dude who desperately wants a career as a DJ, but—believe it or not—he’s having a hard time turning turntables into rent money. After his girlfriend threatens to leave him if he doesn’t get gainful employment, Pete finds himself apprenticed to one Tommy Rag, a revolting door-to-door vacuum salesman played masterfully by Timothy Spall. Tommy careens around town in a filthy car peddling vacuums to people who can’t afford them and spouting cynical aphorisms about selling to an appalled Pete. It’s a hoot.
What you can learn: Buyer insights make a difference. Not to give it away, but Tommy Rag is so focused on closing deals and winning a holiday on the beach that he fails to realize that his industry is collapsing around him. Door-to-door sales was already mostly a thing of the past back in 2001, but Rag never pulled his head out of his book of leads long enough to notice. Sure, you’ve got to focus on hitting your number, but you’ve also got to keep your eye on the big picture. When industries change—and they change fast these days—you’ve got to shift your tactics to meet buyers’ new expectations.
1. “Glengarry, Glen Ross”
You knew this was coming, but we’re not going to apologize. “Glengarry, Glen Ross” is hands-down the best sales movie of all time. If, somehow, you haven’t seen it, you need to change that; if you have seen it, you should watch it again. It’s exceptional on too many fronts to even count, and Alec Baldwin’s 10ish minutes of screen time should’ve netted him an Oscar for his classic motivational speech.
What you can learn: “Coffee is for closers.” You don’t sell, you don’t eat (or drink). Sales can be an unforgiving profession with little margin for error, so if you’re not armed with the best tools, the latest inside insight, and the right approach, you’ve got no chance of closing your deals and earning access to the coveted Glengarry leads.
There are a ton of other movies about sales, ranging from pretty darn good to bargain bin garbage. But these are the best, and there’s a lot you can learn from each of them. Perhaps the biggest takeaway from them is that the range of sales experiences, from glitz to glum and everything in between, hinges on how well the sellers themselves prepare and how dedicated they are to perfecting their craft. In short, whether you end up in the penthouse or the poor house is all up to you—so arm yourself accordingly:
Image copyright New Line Cinema 1992
