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.
Rob tells Laura that other women are just fantasies, Laura is reality, and he never tires of her. He proposes marriage; she thanks him for asking. She arranges for him to revisit his former love of dee-jaying. At the celebration of the newly released single by Vince and Justin, where Barry’s band Sonic Death Monkey plays “Let’s Get It On”, Rob is surprised that Barry’s band is not a disaster.
Rob makes a mixtape for Laura and feels he has finally learned how to make her happy.