10 Best Sales Movies to Binge this Weekend

The movies every sales rep should know

Looking for a good sales flick to get you fired up this weekend?

Look no further, my friend.

We’ve got the list of the 10 best sales movies that will have you ready to run through a brick wall (or just make more cold calls). These movies embody the spirit of sales and show not only the highs but also the lows of the life of a salesman. So grab some popcorn, a La Croix, or your drink of choice, and get ready for some sales classics.

1. Glengarry Glen Ross (1992)

If you’re in sales, the phrases "ABC. Always be closing" and “coffee is for closers” are something you’ve likely heard a time or two (or 100). The movie is about a group of salesmen facing a high-pressure sales competition to keep their job in a real estate office. It goes without saying, this movie is a classic and must-watch for every salesperson. And not to mention the all-star lineup… Al Pacino, Jack Lemmon, and Alec Baldwin bless us with their acting genius.

2. Air (2023)

This is the newest one on the list but one of our favorites. Although it doesn’t highlight traditional sales tactics or culture, it’s a masterclass on closing a deal. The movie is about the true story of Sonny Vaccaro (former head of Nike Basketball) selling Michael Jordan on joining the Nike Brand and forming the “Jordan Brand”. And you can never go wrong with Ben Affleck and Matt Damon as the two main characters.

3. The Wolf of Wall Street (2013)

This one’s a gimme. You can’t make this list without it. The Wolf of Wall Street is the most well-known sales movie of the past 2 decades, but you probably want to skip this one for family movie night. The movie is based on the true story of Jordan Belfort and shows the ups and downs of being a world-class salesman with shady business practices.

4. Jerry Maguire (1996)

If she doesn’t know the line "Show me the money!", she’s too young for you. This movie is a classic and is a must-watch for anyone that’s in sales. Tom Cruise plays a sports agent who works his as* off to try to sign a star athlete. The film is loosely based on a real-life sports agent named Leigh Steinberg, who represented over 300 professional athletes over his career. The movie went on to win an Oscar and go down as a sales movie classic.

5. Boiler Room (2000)

If you like the idea of the “Wall Street lifestyle” this movie is for you. Lots of cold calls, big money, drugs, and flashy cars. This movie has it all. Not to mention, the all-star cast featuring Vin Diesel, Giovanni Ribisi, and Ben Affleck all playing key roles. It’s a bit of a cautionary tale about the dangers of greed in sales, and the importance of doing the right thing.

6. The Goods: Live Hard, Sell Hard (2009)

This cheesy comedy follows a “legendary” salesman (Don Ready) and his team who try to save a struggling car dealership in just one weekend. Loaded with persuasion techniques, witty banter, and outrageous schemes, this movie is exactly what you’d expect from a used car salesman movie. If you’re in the mood for a trashy cheesing flick, this is the one for you.

7. Tommy Boy (1995)

This movie is a timeliness classic, with two comedians in their prime. The story is all about Tommy Callahan (Chris Farley), a struggling salesperson who has to save his family's business with his sidekick Richard (David Spade). The two go on a road trip filled with failed sales pitches and unreal scenarios. Put this one on your list and let Tommy Boy be your mentor in the wild world of sales.

The Pursuit of Happyness (2006)

This one is a drama based on the true story of Chris Gardner, a struggling salesman who becomes homeless with his young son. Will Smith delivers an inspiring performance playing Chris Gardner and features Will’s real-life son (Jaden Smith) as his son in the movie. If you’ve had a tough week and need to let out a couple of tears (no shame) give this movie a watch.

9. The Founder (2016)

This movie tells the story of Ray Kroc, the man who turned McDonald's into a global empire. Michael Keaton takes on the role of Ray Kroc and does a hell of a job. Ray Kroc stole built the most iconic fast-food brand in the United States, but it was no easy task. This film shows the ambition he had to overcome roadblocks, and most importantly… the sales skills he used to persuade people.

10. The Internship (2013)

This comedy follows the adventures of two failed salesmen, played by Vince Vaughn and Owen Wilson, who struggle to find another job, but somehow land internships at Google. Vince and Owen show that their soft skills can be immensely valuable when partnered with the nerdy coders on their team. This one is a win for all the non-technical salespeople out there (like me).

That’s all we got ladies and gentlemen. Time to sink into that couch, and get fired up to close some more deals.

Happy selling. ✌️