Dave O’Meara is an average guy in his late thirties, recently deserted by his girlfriend and laid off from his minimum wage job in a small town in Iowa.
As Dave punches out of his warehouse job for the last time, his glance is caught by a newspaper article tacked to the staff bulletin board. “Lottery Winner leaves for Sunshine State,” reads the headline, and underneath it is a photo of Dave’s former co-worker, Randy Russell. Emboldened by the realization that he now truly has nothing left to lose, Dave packs his bags and sets off to find Randy’s new home.
Along the way Dave picks up four misfits, all wanting to turn their lives in a new direction, but none of them certain where to go or how to get there. Traveling across the country in Dave’s cramped ’83 Buick, the five characters make their way to Florida in a comical unfolding of events and personalities.
The first stop is The Pyramid karaoke restaurant. Didier is Dave’s 23 year old bumbling waiter. Stuck at a job for which he has no enthusiasm and little aptitude, Didier listens eagerly to Dave’s plan for a new life. In the midst of yet another chewing-out from his boss, Didier sees Dave leaving and quits on the spot.
Melissa, 27, is just coming out of a five year relationship that ends explosively in front of Dave and Didier at a rest stop in Kentucky. When Melissa’s boyfriend drives off and leaves her stranded, the ever-helpful Didier offers her a ride in Dave’s car. Still dazed by the incident, Melissa accepts and the three continue south.
Nicole, 26, and John, 28, are an unmarried couple attempting to save their strained relationship by moving from Indiana to John’s parents’ home in Florida. Nicole is shy but manipulative. John appears to be a normal, well-adjusted guy, but his uptight and high strung tendencies are brought out by even mildly stressful situations. Dave, Didier and Melissa find them at a gas station in a small town where their car has just broken down. With John’s keen sense for storytelling and Nicole’s mixed-up optimism, the two become welcome additions to the group.
THE WINNER is the story of five people on a quest for better lives. Each character has their own expectations of what they’ll get when they meet the mysterious lottery winner, but in the end each will find something entirely different.