The All-Time Top 10 Movies for Sales Professionals
It's good to be back, readers. Let's dispense with the pleasantries and jump right in.
Last summer, I was forced to put InsideSales.com in its place by revising their terrible list of top songs to pump up sales reps. For this post, I'm taking the gloves off once again.
Over the weekend, I conducted a quick Google Search of top 'sales movies'. To my horror, I found this impossibly bad list from HubSpot ranked #1. Scan Hubspot's list of top sales movies. Now, erase it from your memory. Sales is not the sleazy negative stereotype portrayed in the films comprising Hubspot's list. Sales is a way of life that permeates everything we do.
Ask your crush to go on a date? You're selling. Request a raise? You're selling. Convince your kid to do his or her homework? You're selling. Fght with your significant other over nightly viewing options on Netflix and Amazon Prime? You're definitely selling.
Moral of the story: never let snooty film critics tell your sales force what movies they should be watching. Let the Apex Predator handle that.
The All-Time Top 10 Movies for Sales Pros
The 10 movies I've selected below may not explicitly be about sales - but they are the most essential movies that every sales professional should watch. They show the game for what it is - and inspire you to go out and crush it without mercy. Most importantly, they give sales the gravitas it's due - which is why you won't find any movies about dancing used car salespeople in this list. Sorry, Matthew Chernov.
Let's get to the list. In reverse order, here are the best sales movie scenes from my top 10 essential moves for every sales professional, plus links to free or super-cheap services where you can stream them on demand.
#10. The Big Short (2015)
Sharing an incredible scene below from Adam McKay's underrated chronicle of the 2008 mortgage crisis. Every time I watch this scene, I feel a powerful appreciation for Jared Vennett (Ryan Gosling's character). Think what you're selling is complex? Try selling an investment against major finance industry investments that revolves around concepts like credit-default swaps and collateralized debt obligations.
Welcome to sales, comrades. This scene is poetry-in-motion. The scene-setting. The Jenga visual metaphor. The deft combination of zero-bulls**t selling (Gosling's explanation of the conditions creating the impending crisis) with harmless-yet-effective bulls**t ("That's my Quant!"). The Big Short belongs on the reading list of every civics student and every sales professional.
Watch Free: Netflix.
#9. The Pursuit of Happyness (2006)
Hiring Manager: "Chris, what would you say if a guy walked on without a shirt on ... and I hired him??"
[Pause] Chris: "He must have had on some really nice pants."
The Pursuit of Happyness is the only film on my list that verges on sappy. That's because every sales professional should see the ability of Will Smith's character, Chris Gardner, to deploy humor this effectively in the midst of ravenous hunger and full-tilt desperation.
When you, as a sales professional, find yourself up against the wall. Fearing termination. Facing an impossibly high quota. Down to your last few outs. This is the pathos you need to exude - an incredible, powerful conviction in your ability to help your prospect - crossed with infallible looseness and good humor.
#8. Jerry Maguire (1996)
The movie on this list with the highest date night approval rating - Jerry Maguire has 5 or 6 must-watch scenes for every sales professional. What I love most - the movie's plotline contrasting Maguire's commitment to his clients with his fear of commitment to Renee Zellweger's character. Maguire succeeds as a sports agent because he is utterly obsessed with his clients - making them successful, meeting their needs, showing them the money.
There's a famous sales quote from Mary Kay Ash, "Pretend that every single person you meet has a sign around his or her neck that says, 'Make me feel important.' Not only will you succeed in sales, you will succeed in life.” This movie illustrates that in spades. Help your sales team help themselves. Add Jerry Maguire to your must-see list as a sales professional.
#7. Tommy Boy (1995)
Do I really need to explain the exuberant wisdom of Tommy Boy to you people? My sense is that everyone over the age of 30 has seen this movie and loved it. For you young whippersnappers, though, here's a quick elevator pitch. This is the funniest sales movie of all-time. Period.
Watch Chris Farley handle objections (see: above). Watch Chris Farley completely lose his s*it in front of a prospect. Watch Chris Farley infuriate his colleague (David Spade) on the road. It's all funny as hell. You can put your head up a butcher's a** or just take my word for it.
#6. Wall Street (1987)
For the purist, it almost gets no better. I'm docking this a few spots because a) too obvious and b) it doesn't hold up like the top 5 movies on this list - in terms of rewatchability. With that aside, let me call your attention to the below scene.
Forget "greed is good." Gordon Gekko's monologue here is where it's at, in terms of sales. "I've been in this business since '69. Most of these Harvard MBA guys don't add up to dogs***t. Give me guys that are poor, smart, hungry and no feelings. You win a few. You lose a few. But you keep on fighting - and if you need a friend, get a dog. It's trench warfare out there, pal." That is where it's at. You won't find a lot of people quoting this scene, but there are a dozen others like it that are equally slept on by the general public. Get back in touch with Wall Street; classics never go out of style.
#5. The Wolf of Wall Street (2013)
I don't care how much prison time Jordan Belfort has done. The movie lives, eats, sleeps, and breathes the concept of sales in its purest sense. Selling the dream. Selling need. Product? Irrelevant. Whether it's penny stocks or pens, it matters zero.
Also carrying the The Wolf of Wall Street into my top 5: sheer rewatchability. This is the shortest 3 hour movie on record. Leonardo DiCaprio's top-notch performance captures the salesperson at his/her best and worst. As a cautionary tale, it veers from deathly serious to utterly hysterical - often at the turn of a single line. Watch. Re-watch. And enjoy.
#4. There Will Be Blood (2007)
Daniel Plainview would drink Gordon Gekko's milkshake. The rags-to-riches tale of an enterprising oil tycoon shows the ascent of Plainview (played impeccably by Daniel Day-Lewis) from ditch-digging oil prospector to crafty entrepreneur to morally-compromised kingpin.
The above speech captures the inherent salesmanship of Mr. Plainview. The insistence on a face-to-face pitch. The self-humanizing touch. ("I work alongside my son, H.W."). The assertion of "why." ("It's an abomination to consider that any man, woman or child of ours should look upon a loaf of bread as a luxury.") This is how you convince a town full of people to let you drill on their land, buy real estate, buy software - whatever. Get your salespeople in touch with their inner Daniel Plainview - minus the misanthropy. Then sit back and enjoy the milkshake.
#3. Boiler Room (2000)
Most underrated sales movie on the planet. You won't find this film on Hubspot's list (though you will find something called Cedar Rapids). That's probably because the average film critic has zero idea what life looks like inside an actual call center. And in turn, have even less clue that Boiler Room, by-and-large, is the most realistic depiction of a modern sales floor in cinema.
Yes, it's another movie about an ethically questionable business. Yes, its fictional sales organization is troubled by the same afflictions that plague The Wolf of Wall Street - overt sexism, fraudulent business practices, the male id run amok, et al. Remove those from the equation and take a step back. The training scenes, the depiction of camaraderie and competitiveness, the wealthy-yet-clueless young reps. Those are as real as it gets to this day. And Boiler Room is nearly two decades old! If you work in an inside sales environment, give it a fair shake and see the most recognizable adaptation of your daily existence, as a sales professional.
#2. The Godfather (1972)
Before entering my career as a salesperson, I loved The Godfather. Was one of my all-time favorite movies. My family watched this film together every Christmas, growing up. And I'll never forget the first Christmas we watched it together after I had joined the ranks of the sales profession. I was 9 months into my career selling six-figure software deals. It was like a light went on.
The opening scene of this movie completely changed the way I thought about my sales pipeline. Like the mortician, Amerigo Bonasera, as pictured in the scene above coming to the Godfather, I had been approaching my prospects out of the blue with an immediate request. Sure I was offering help, instead of seeking it, but who was I to be requesting their time out of the blue? Moving forward, I added a new part to my outreach process - where I found ideal clients, reached out with some immediate value ["I see you sell [x]. Know a great fit I can introduce you to."] and began building an authentic, mutually beneficial relationship based on trust. Then, with my late-stage prospects, I began opening conversations with a single line: "[Prospect X], we're very close to making this happen. How do I make this an offer you can't refuse?" I s*** you not. That was over a decade ago. I continue to do both to this very day. Watch The Godfather and take in its fundamental principles on how business gets done - whether you're a Mafia leader or an enterprise sales representative.
#1. Glengarry Glen Ross (1992)
After a 3 year hiatus, I rewatched Glengarry Glen Ross last month. It's the perfect sales movie. It's ageless. It's so much more than "Always be closing!" and "Coffee is for closers." Want to invalidate your top 10 movies for salespeople list? Leave Glengarry Glen Ross out of your top 5. Hubspot and Matthew Chernov, what were you smoking?
And best of all, it's free on Netflix as of this writing. Watch this freaking film, sales professionals, and see six men, Al Pacino, Kevin Spacey, Jack Lemmon, Ed Harris, Alan Arkin and Alec Baldwin, who cover the entire terrain of the profession with pitch-perfect pathos. When it comes to the sales profession, Glengarry Glen Ross is your Citizen Kane.
Watch Free: Netflix.
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