Storytelling Lessons From Tommy Boy

There is a great scene from the movie Tommy Boy that displays the power of storytelling in a silly but meaningful way. 

Tommy, played by Chris Farley, is in a restaurant with his friend and business partner Richard, who was played by David Spade. Tommy is the son of “Big Tom’ Callahan, the owner of Callahan Auto, a successful auto parts business in Sandusky, Ohio. And even though “Big Tom'' is a master at sales, Tommy, or Tommy Boy as he is known, is not the sharpest knife in the drawer. 

It took him seven years to graduate from Marquette University, and even then, he barely made it out. Tommy Boy is gifted given an executive position within the company. This annoys Richard, who has been a loyal, hardworking employee and understands the nuances of the company and the business. Tommy Boy is set to cruise through life in his cozy office with the mini fridge and the Star Wars fan.

But during his fathers wedding, ‘Big Tom’ collapsed while dancing and, to the shock of the guests, died of a massive heart attack on the spot. The company is sent into disarray, as the heart and leader of the company was suddenly gone. All of the hopes, to keep the company going and save the jobs of all of the employees, rested on the giant shoulders of Tommy Boy. 

The problem is, he sucks at sales. And without the trust that his dad had, the bank backed out of a promised loan for their new brake pad division. On top of that, they wanted immediate payment of all of the debt that the company owed. So it is up to Tommy Boy to go cross country, to try to sell a certain amount of brake pads to get the money to keep the business alive. 

Hilarity ensues as Tommy and Richard hit the road together. Each step of the way, the lack of experiences, social awkwardness and immaturity that Tommy Boy exhibits leads to failure after failure in attempting to close some deals. He tries to imitate some of his fathers stories and jokes that always worked but he couldn’t pull it off. 

After another embarrassing scene where the failure continued, Tommy and Richard sit down at The Cluck Bucket for a meal, both still smarting by how poorly everything is going. A grumpy and obviously overworked waitress comes over to take their order. Tommy is really craving chicken wings and attempts to place the order but she explains that the kitchen is closed until dinner and they are currently only serving cold items and desserts. 

Tommy tries once more to see if he can get those wings, and the waitress quickly and coldly shuts him down. After resigning himself to consuming a sugar packet for his meal, Tommy changes his demeanor and asks what the waitress's name was. You see her, for a moment, have a human emotion as she says that her name is Helen. 

Tommy then compliments her and attempts to bond with her by acknowledging that they are both in sales. And he goes on to explain why he sucks at sales. When he starts telling the story, she sighs and briefly turns away, obviously annoyed by this entire situation. But Tommy Boy continues. He explains that whenever a client is even a little interested in buying something, he makes fun of himself by showing how ridiculously excited he gets at the chance. 

Each time this happens, Tommy Boy treats this potential opportunity as a precious “little pet”, and he describes in physical humor as only Chris Farley can, how he winds up destroying that pet every time. During the scene, he has Helens full attention even as she looks disturbed by what he is saying. 

After his emotional outbreak within the description, Tommy regains his composure immediately. And with the cool calm and demeanor as his dad had, he bonds himself and Helen together with the words describing how people like them need to forge ahead. 

“God, you’re sick,” she says while shaking her head. 

“I’ll tell you what,” she says. “I’ll go throw the fryers on and throw some wings on for you.”

Richard looks stunned by what Tommy Boy just pulled on. Tommy had no clue, he was just happy to get the wings. Richard asked about how he just completely turned around that situation with Helen. Why can’t he sell like that?

“I was just having fun,” he described. “If we didn’t get the wings, so what? We still have the meat lovers pizza in the trunk.” 

Richard explained that he got the wings because he was relaxed. He showed that Tommy got the wings because he had confidence. And he got the wings because he knew how to read people, just like his dad knew how to do. 

All of those things are accurate and they all are important. But he didn’t get the wings solely for any of those reasons. He got them because he was able to wrap his relaxation, his confidence, his ability to read people into a fabulous story. A story that shifted Helen from a grumpy cynic into a helpful advocate in a matter of minutes. 

That’s what great storytellers do. They fearlessly show up- either one to one, through their voice, through their written words or up on stage in front of strangers. And they tell stories that turn strangers into friends. They tell stories that turn non believers into believers. They tell stories that change the world, one person at a time.