Despite being one of the largest professions in the world, it’s amazing how little entertaining content there is for salespeople. You would think that a profession that boasts nearly 13% of the entire U.S. working population would have scores of sales movies, books, and tv shows dedicated to entertaining them.

There are, however, a handful of truly compelling sales movies that capture the drama and absurdity of life in sales. Here are the ten that have truly made a mark on the profession (Warning: some of the clips are NSFW).

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10. Tin Men

Set in 1963 Baltimore, Tin Men is a tale of rivalry between two aluminum-siding salesmen played by Richard Dreyfuss and Danny DeVito. Their competition starts after one crashes his Cadillac into the other’s, triggering an escalating sequence of events that drives them to greater extremes in an attempt to get even. The movie’s tagline was: The American Dream Changes. The People Who Sell It Don’t.

9. The Prime Gig

This obscure movie is relatively unheard of in the sales community despite starring Vince Vaughn and Ed Harris. Vaughn plays Pendleton “Penny” Wise, a skilled telemarketer whose company goes bankrupt, forcing him to work for telemarketing legend Kelly Grant, whose new venture selling shares in a goldmine may not be completely above board. The movie features scenes like this one, which is legendary in its own right.

8. Seize the Day

The late Robin Williams plays down and out salesman Tommy Wilhelm in this film adaptation of Saul Bellow’s novel. After losing his job, breaking up with his girlfriend, and having a nervous breakdown, Wilhelm packs up and moves to New York City to start a new life. While more raw and emotional than the other movies on this list, the talented Williams captures the stresses of balancing personal issues while seeking success like no other actor could.

7. The Pursuit of Happyness

Will Smith’s role as entrepreneur Chris Gardner and his nearly yearlong stretch of being homeless may not be immediately associated with sales, but it should be. Gardner is a salesman who invests his life savings in experimental medical devices that he has a hard time turning a profit on, leading him to the loss of his residence, and eventually his wife. This touching story shows Gardner’s challenging climb to success as he pursues a career as a stockbroker while trying to find a place to live for his son.

6. Used Cars

Before Robert Zemeckis swept the Oscars with Forrest Gump, he wrote and directed Used Cars which starred Kurt Russell as a car salesman angling to get into politics. Irreverent and hilarious, this flick covers nearly every single stereotype of car salesmen, as the main characters lie their way from one manipulative sales scheme to another. If you want a glimpse into how comedies used to be, this is the movie for you.


5. Tommy Boy

This movie is usually on everyone’s list of favorite sales movies, as Chris Farley effortlessly plays a dimwitted heir to an automobile supply company – tasked with saving his late father’s business from a conniving mother-in-law and a bank eager to foreclose on the company. Tommy travels the country trying to sell a line of brake pads, while learning how to become an effective salesperson.

4. Boiler Room

Considered to be the Wall Street for the modern era, Boiler Room takes a dynamic look at cold-calling, selling, and compromising your morals for the sake of making big money. Giovanni Ribisi plays a college dropout running an unlicensed casino in his apartment who gets recruited to sell stock for J.T. Marlin, in what turn out to be fake and expired companies. The movie expertly takes you through the lure of massive wealth, the thrill of the close, and the moral consequences of deceiving your fellow man. It’s a must-watch for all salespeople, and includes this famous scene with Ben Affleck.

3. The Wolf of Wall Street

While it’s become an iconic sales movie, what’s little-known about The Wolf of Wall Street is that Boiler Room is actually based on the same tale, that of Jordan Belfort and his controversial firm, Stratton Oakmont. Leonardo Dicaprio plays Belfort, an unscrupulous, manipulative, and drug-addicted owner of a brokerage firm that sells worthless penny stocks to an unsuspecting public. While the true story may be somber, director Martin Scorsese makes this film border on satire, as the comedic aspects drown out any life lessons we’re supposed to learn from Belfort’s cautionary tale.

2. Suckers

A cult classic by the standard of sales movies, Suckers purports to tell the real story about what goes on at car dealerships. Opening in 2001, the film was never actually released in the United States. The plot involves a good guy who falls into debt with some loan sharks and attempts to make good by getting a job at a car dealership, where he is taught the ropes and all the tricks of the trade. He soon becomes the top salesman at the dealership, trying to settle his debt before it’s too late.

1. Glengarry Glen Ross

This film adaptation of David Mamet’s award-winning play, Glengarry Glen Ross is considered by many to be the best sales movie of all time. The famous scene below with Alec Baldwin as a hard-charging sales manager features some of the most quoted lines in the sales industry. What less people know, however, is that Baldwin’s character Blake wasn’t part of the original play and was only written in for the movie version. If you work in sales, and you haven’t seen Glengarry Glen Ross yet, then it should be your personal goal for the week.

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About the Author Ken Kupchik

Ken Kupchik is the creator of Sales Humor and the author of the funniest sales book ever written, The Sales Survival Handbook, which you can order on Connect with him on LinkedIn.


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