Rob Gordon is a music-loving man with a poor understanding of women. After being dumped by his long-term girlfriend, Laura, he tries to understand how he failed in his relationships by seeking out his old partners.
By day, he works at his record store, Championship Vinyl, where customers drift through. He and his employees Dick and Barry, armed with an encyclopedic knowledge of all things musical, compile "Top 5" lists for every conceivable occasion, openly mock the tastes of their customers, and sell a few records.
Two shoplifting, skateboarding teenagers, Vince and Justin, are an annoyance to them until Rob listens to a recording that they made as The Kinky Wizards. He offers them a record deal, the first under his own label, Top 5 Records. During his off-hours, he pines for Laura and tries to win her back.
Laura's father, who liked Rob, dies. Rob attends his funeral with Laura. Shortly after the reception, Rob realizes he has always had one foot out of the door and never committed to her—and in doing so, neglected his own future. They resume living together. He meets a music columnist and develops a crush, but wonders while making a mixtape for her if he would always be jumping from rock to rock.
