Solitary Man tells the dryly funny yet all too relatable story of Ben Kalmen (Michael Douglas), a fifty-something New Yorker and former successful car dealer, who through his own bad choices lost his entire business. He's also divorced from Nancy (Susan Sarandon), his college sweetheart and the one person who knows him better than anyone. Although he still finds the time for his daughter Susan (Jenna Fischer) and her adoring grandson, his role as more of a friend than father or grandfather is starting to wear thin on the family. His girlfriend Jordan (Mary-Louise Parker) is the daughter of a very influential businessman who's on the board of a major auto manufacturer. If Ben can just keep his hubris in check for a little while longer, he will be back as big as ever, but some of the same motivations that lead to his demise are threatening to take him down again, and for good.