A quixotic advertising salesman embarks on what he sees as a noble quest to help business owners succeed, but the business owners treat him like dirt because they see him as just another salesman.

SYNOPSIS:

Salespeople. They're intrusive and pushy. We're wary of their sales tricks and suspect their motives are ultimately self-serving when they ask, "May I help you?" TILTING AT WINDMILLS is about an exception to this dehumanizing stereotype, and his name is Andy.

Andy rides off in his old white Ford Bronco into the small towns fate led him to sell radio advertising to the local business owners. These owners dread the intrusive visits from salespeople and are ready to greet them with disparagement. But Andy doesn't see himself as a salesperson; he actually resents the epithet. He sees himself as helping business owners fulfill their entrepreneurial dream. With ideas his sword, confidence his shield, and Abby his courtly love, Andy could endure the owners, earn their investment without resorting to the use of "sales tricks," and help them in a struggling economy.

Andy had been successful in the early goings of his noble quest, but decides to give it up because he can no longer withstand the owners' contempt. Greg Lance, a former salesperson who owns the radio group Andy works for, talks Andy out of quitting by reminding Andy of his former glory, and Rhonda, a fellow salesperson, assures Andy his struggles are due simply to being in his first slump. But Andy knows the real reason: Abby broke off their engagement in a letter with no explanation and instructions not to contact her, and it has been her ambiguous rejection of him that left Andy heartbroken and impotent to stand up to the owners. Due to Andy's chivalrous nature, he respected Abby's wishes and never reached out to her. But when she comes back into his life, Andy discovers the reason why she left him: she's pregnant and Andy is not the father. Despite Andy's insistence they be together regardless, Abby can't see past her guilt. Abby tells Andy goodbye for good; he acquiesces.

Now disillusioned and frustrated, Andy has his big meeting with Bradley, the slickster owner of an area car dealership whom Lance has hinted signing will put Andy in good standing to become the next Director of Sales. Andy tries to get Bradley off the fence of the six-figure advertising proposal with his usual honest tact, but when Bradley won't budge, Andy "sells out" and debases himself by using a "sales trick" in a desperate attempt to persuade Bradley. But after watching Bradley congratulate one of his salesmen for tricking a poor single mother into buying a minivan she can't afford, Andy has his epiphany; he is NOT a salesman. Andy gives the slickster a taste of his own medicine, quits his job, then drives off in his white Bronco towards whatever his next adventure may be.

Quarterfinalist: Shore Scripts Feature Contest (2018)

TILTING AT WINDMILLS