The best sales movies to watch in 2020

By Graham Collins
The best sales movies to watch in 2020

Are you working from home due to COVID-19 like a lot of salespeople? You probably burned your way through Tiger King months ago, finished the Aaron Hernandez documentary in one sitting. Maybe you’ve even binged through Babysitter’s Club. So what now? Well, there’s the (admittedly niche) category of sales movies that every good salesperson should watch at least once in their lifetime. You’ve probably seen a few of these sales movies, but why not check a few more off your list!

Glengarry Glen Ross (1992)

Okay, you can’t have a list of sales movies without including this classic. You can barely walk through a sales floor without hearing an account executive telling a sales development rep that “coffee’s for closers”. Next thing you know you see a sales manager writing “Always Be Closing” on a whiteboard. It’s over the top and it’s not really applicable to modern selling. If you want to earn respect in a sales pit, you have to watch it. I don’t make the rules. Bonus: Alec Baldwin gave a Christmas parody reprisal of his famous character on SNL as an elf version.

Salesman (1969)

This is a dark horse movie and don’t be surprised if you’ve never heard of it. It’s a documentary made in 1969 that follows four bible salespeople as they travel across the eastern seaboard of the US. A fascinating look into the real world lives of the salespeople who blazed the trail for us all. It’s a bleak look at the lives of 1960s salespeople and it will make you thankful for screen shares and cell phones. Also, if you’re struggling to hit your quota right now, you will definitely relate to one of the main characters, Paul. Then as soon as you finish it, you can watch the hilarious parody of it called ‘Globesman’, an episode of Documentary Now on Netflix. A rare option, but one that should be on your list of sales movies!

Tin Men (1987)

Another look at door to door salespeople, but a less realistic and funnier view on what it’s like to sell in a bygone era. Plus anytime you can get Richard Dreyfuss (Bill “BB” Babowsky) and Danny Devito (Ernest Tilley) on the screen at the same time, I’m in. It takes place in the 1960s and balances humor with drama well. Don’t expect to pick up any LinkedIn prospecting tips, but it’s worth checking out.

The Wolf of Wall Street (2013)

The classic sales interview question “sell me this pen” had been asked for years before this movie. And the nonchalance and swagger with which Leonardo DiCaprio asks it is unmatched. Although the response that he accepts as a great answer is hotly contested, it remains a frequent sales interview question. In addition to this scene, the movie shows a raucous and at times unbelievable look into the lives of stockbrokers in the late 1980s.

Jerry Maguire (2000)

The most famous scene in the movie, “SHOW ME THE MONEY”, could be a case study in how to retain clients. I’m serious, sales professionals have at least three major takeaways from this scene. Tell them what they need to hear while being realistic on your expectations. Match their tone; if they’re excited and joyful, you should be too. Use your listening skills to determine what exactly is most important to the client — in this case it’s the money. Be prepared to put yourself out there and ask for the business. Oh, and don’t be afraid to get on the phone with your clients! Even if you have to use a late 90s flip phone like Cuba Gooding Jr. and Tom Cruise.

The Truman Show (1998)

Bear with me on this one, I know it’s not like most typical sales movies. I’m specifically talking about a phenomenon in sales that I refer to as “happy ears“. All salespeople know this situation. The client has no objections to your sales pitch. Your prospect has no questions about the pricing. A prospect who has no questions and no objections seems like a perfect situation, but that’s not the reality of the situation. The reality is that they are bored or made up their mind on another vendor and don’t care to listen to you. The reality is that you’re going to lose that prospect to another provider, one who asked questions and had objections. What does this have to do with The Truman Show? Well, at the beginning of the movie, he has life “happy ears”. His life is easy, everything is perfect, and everything works out for him. If he had asked more questions (or offered more objections) the reality of the situation would have been more apparent. At the end of the movie, he does and the truth is revealed.

Your favorite sales movies

Honestly, there are countless sales movies you can learn from! If you know what to look for, just about any movie can teach you something about sales. If you’re looking to learn more about sales, you should check out the QuotaPath blog, which features frequent sales training… and sometimes fun lists! Feel like I missed some great sales movies? Send them my way!

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