Request demo

6 Must Watch Funny Sales Videos

4 minutes read

They say laughter is the best medicine. You’re sitting at your desk, drowning in a sea of spreadsheets and sales reports, when suddenly, a video pops up on your screen. Within moments, you find yourself doubled over with laughter. Sales is often associated with pressure and stress; a refreshing break is much needed.

After multiple searches, below is a list of some funny sales videos. Feel free to take notes from these examples for your upcoming sales meetings (or what to avoid when giving your pitch). Go ahead and have a laugh!

1. The Iconic “Sell Me This Pen”

In the movie “The Wolf of WallStreet,” there’s an iconic scene where Jordan Belfort, played by Leonardo DiCaprio, challenges his colleagues to sell him a pen. The scene highlights the importance of effective sales techniques and showcases Belfort’s charisma and persuasion skills. It’s a masterclass in salesmanship, demonstrating the art of creating demand and highlighting the unique features and benefits of a product, even something as simple as a pen.

2. A better pitch than Don Draper?

In the TV series “Mad Men,” Don Draper delivers a poignant pitch for the Kodak Carousel slide projector that goes beyond product features. He taps into nostalgia, highlighting the device’s ability to transport people back to cherished memories captured in photographs. It’s a testament to the power of storytelling in sales, motivating sales reps to sell not just a product but an experience.

image getting

3. Up-selling Genius like Eugene Levy

In the movie “Serendipity,” Eugene Levy a sales rep at Hermes store, takes the opportunity to upsell. When John Cusack’s character shows up enquiring about a billing history, Eugene, turns it into a sales opportunity.. By suggesting items like a tie and then upsellig him a suit, he not only demonstrates his quick thinking but also showcases the art of suggestive selling. A valuable skill for sales reps.

4. Always Be Closing

In the iconic “Always Be Closing” (ABC) sales scene from the movie “Glengarry Glen Ross.” Alec Baldwin’s character delivers a speech to a group of struggling real estate salesmen. He emphasizes the importance of closing deals and warns them of the consequences of failure. Baldwin’s character uses aggressive language and intimidation tactics to instill fear and urgency in the sales team. The scene is a powerful depiction of the high-pressure environment of sales and the tactics employed to achieve success in the industry.

Pro Tip- You don't have to create high pressure, instead create sales contest to motivate your sales team. Design your Sales Contest in 3 simple clicks.

5. Laugh and Learn from Tommy Boy Sales Pitch

The movie- “Tommy Boy,” featuring the comedic duo David Spade and Chris Farley. Farley’s character delivers a side-splittingly terrible sales pitch for his supposed incredible brakes. The scene serves as a cautionary tale on the perils of overselling, reminding us how it can easily backfire. The highlight? Farley’s character goes all out, even setting a car on fire, only to wrap it up with the punchline: “All because you want to save a few extra pennies…”. A perfect example of how humor can lighten the mood, even in sales training sessions.

✅ To avoid your reps getting backfired, introduce thorough sales coaching.

image getting

6. A Perfect Sales Role Play

In this classic scene from “The Office,” Michael Scott, the eccentric regional manager, conducts a sales role-play exercise. This involves Jim Halpert and Dwight Schrute, two salesmen, acting out a fictional sales call. However, instead of focusing on the intended training, Michael hilariously derails the exercise with absurd interruptions and prompts, much to the frustration of Jim and Dwight. The scene brilliantly captures the humorous take on the challenges of sales training and management.

image getting

Bottom Line

As we wrap up, we have had a humor blast exploring these six hilarious sales videos together! At SmartWinnr, we believe even in the high-pressure world of sales, it’s important to find moments of humor and levity. To do this, it’s equally important to track if our reps can have meaningful conversations with customers, engage them and drive results.

To know more how you can create a sales contest, drop your queries at

Want to gamify your training?

‘Work from Home Warriors’: Sales Training Game for Remote Sales Teams

7 sales training games that actually boost your sales team skills

Upskill Your Sales Team with AI Role Play Revolution

Looking for sales training software to motivate your sales reps?

Explore SmartWinnr’s Learning and Gamification features and learn how to run a fun and engaging sales training for your team.

Published on Mon Apr 29 2024

Ready to double your sales numbers?

Schedule a demo with our team to see how SmartWinnr can drive sales productivity in your organization. Or talk to us about your challenges and if SmartWinnr can help.

Request demo Free Consultation