Five Best Movies for Sales Representatives to Watch

Five Best Movies for Sales Representatives to Watch

More people than ever are in search of movies to fill their time. Especially with the lack of new entertainment options. If you are in a sales oriented business and wanting to kill two birds with one stone, here is a way to satisfy your need for entertainment while perhaps improving your sales skills. Here are five movies for sales representatives to watch.

  1. Glengarry Glen Ross

A ruthless Chicago real estate office is the setting for this film that makes the top of many sales-themed movies. It gave us such classic phrases like “Coffee is for closer’s” and has had many question whether they had to sell their soul to make a sale. The 1992 film’s cast includes Kevin Spacey and Al Pacino. This can be a real thriller for those who appreciate the exhilaration of the sale.

  1. Tommy Boy

This surprising movie starring Chris Farley and David Spade is much deeper than it may appear on the surface. Faced with saving his families business, Farley’s Tommy Boy character must meet some seemingly impossible sales quotas. Along the way, he learns some valuable lessons about life and sales. There are the occasional fat jokes and low brow humor but at its heart the movie demonstrates there is more to sales than handshakes, looks in the eye and snappy slogans. Plus, it’s fun to watch.

  1. Pursuit of Happiness

If you or your sales team needs a boost of feel-good motivation, check out Wil Smith in this 2006 film. Smith finds himself as a father of a five year old who is in a dire financial situation but has a valued internship opportunity at a brokerage firm. Smith battles a seemingly unending wave of bad breaks and tough luck but continues in his pursuit of the American Dream. It is heart touching and inspiring and will certainly help you appreciate what you have.

  1. Jerry Maguire

Tom Cruise and Cuba Gooding Jr. team up in this classic about a sports agent who regrettably, sends a thesis about the state of his industry company wide. Left to begin again, Cruise is left with just one client, Cuba Gooding Jr. He is joined by a wide-eyed admiring assistant and a goldfish as he tries to regain respect as a high-profile sports agent. The movie is known for giving us “You had me at hello” and, of course, “Show me the money”.

  1. The Wolf of Wall Street

Based on a true story, this 2013 movie stars Leonardo Dicaprio as a stock-broker on a meteoric rise through his industry. This energy and profanity filled film is not for the timid but demonstrates the lengths some will go through to make the sale.


Do you have questions about your insurance? Find an insurance agent near you with our Agent Finder

Search All Blogs

Generic filters

Buzz Your
Insurance Agent

Search for a local agent with our agent finder map.

Agent Finder

Want to learn more about our blog writer?

Read more about KayLynn's background.

Click Here

Search All Blogs

Generic filters

Read More Blogs

Spring Skies and Structural Eyes: Why a March Roof Check is Your Best Insurance Policy

Don’t wait for a leak to check your roof. Learn how to spot late-winter damage and protect your home’s structure this March.

The Mystery of the Plastic Baby: A Guide to Mardi Gras and the King Cake

Why is there a baby in the cake? Discover the history and traditions of Mardi Gras 2026 and the delicious mystery of the King Cake.

Let the Good Times Roll—Safely: Mardi Gras Liability for Your Business

Hosting a Mardi Gras party this Tuesday? Make sure your business has the right event liability and liquor coverage before the beads start flying.

The Business “Prenup”: Why Business Partners Need Life Insurance in February

Love your business partner? Protect your company with a Life Insurance-funded Buy-Sell agreement to ensure the business survives the unexpected.

Heading South? Insuring Your Mid-Winter Break Road Trip in February

Driving to find some sun this week? Check your roadside assistance and rental car coverage before you leave the driveway.

Spring Dreams, Winter Schemes: Updating Your Insurance Before Your Spring Renovation

Planning a Spring kitchen remodel? Learn why you need to call your insurance agent before the contractors arrive to ensure your project is covered.

Shadow or Spring? The Quirky Science and Folklore of Groundhog Day 2026

Will he see his shadow? Dive into the history and humor of Groundhog Day 2026 and why we still trust a rodent with our weather forecasts.

Stocked for Love: Protecting High-Value Valentine’s Inventory with Business Insurance

Is your Valentine’s stock protected? Ensure your business insurance accounts for the massive inventory surge happening in early February.

New Life, New Responsibility: Why a February Arrival Means Updating Your Policy

Welcoming a new family member this February? It’s time to move life insurance to the top of your to-do list to ensure your child’s future is secure.

Delivering Love: The Insurance Risks of Valentine’s Week Gig Work

Delivering flowers or chocolates for extra cash this Valentine’s? Make sure your car is actually insured for delivery work before you hit the road.