There are some great films about salespeople out there. There’s just one problem. Almost all of them are about criminals. Spoiler alert.
The Bad Ones
Hollywood can’t seem to tell a sales story without somebody committing a felony. Here are the biggest offenders.
Glengarry Glen Ross
Al Pacino, Alec Baldwin, Jack Lemmon, Kevin Spacey, Ed Harris, Alan Arkin. This cast alone is worth the ticket. You get a classic late-night sales meeting, the best “go to lunch” moment in movie history, and a great scene where a salesman finally tells off his manager. But the actual plot? A sales team so beaten down and desperate that somebody breaks into the office and steals the leads. Fun to watch. Not a management playbook.
Wolf of Wall Street
The Jordan Belfort story. “Sell me this pen.” Sure, there’s some great phone work in here, and some of the sales scenes are genuinely electric. But the guy was making jerk-off motions at his clients while taking their money, and that’s before you get to the fraud. Don’t be like this.
Boiler Room
Giovanni Ribisi shuts down his illegal basement casino to go sell fake stocks. The best scene is when a newspaper telemarketer cold-calls him, and he coaches the guy into actually making a pitch. Doesn’t work though — Giovanni reads the Times. Good lesson in rejection. Sometimes you lose even when you say the right things. It ends badly for everyone in the boiler room.
Death of a Salesman
Arthur Miller wrote it. Dustin Hoffman and John Malkovich performed it on film. A man who spent his whole life valuing sales relationships over his real ones, only to realize at the end that he’s worth more dead than alive. He pays off the mortgage — by dying in an insurance fraud scheme. Bleak.
The Good One
If you want a sales movie that doesn’t end in handcuffs, watch Tommy Boy. Tommy is a good person. He doesn’t cheat. He grinds, he learns from the people around him, he follows up with old customers. He earns every sale the hard way. That’s what real selling looks like.
Chris Farley and David Spade at their best. They filmed this during downtime from SNL — a show already famous for having zero downtime. Come for the movie review, stay for the trivia.
The Takeaway
The movies that get remembered are the scam stories. But the salespeople who last are the ones doing honest work and building actual relationships. That’s always been true and it’s not going to change.
If you’re trying to build a sales career the right way, or you need to hire sales talent you can trust, that’s what we do. Talk to us or check the job board.