Inspired by events in the life of actor George Hamilton, My One and Only is a charming 1950s-set drama that follows Ann Devereaux (Zellweger), the glamorous but mercurial wife of a philandering society bandleader whose latest infidelity is one too many. Ann packs up her life, buys a Cadillac convertible and with her two teenage sons sets off on a cross-country quest to find herself a wealthy new husband. Ann soon discovers things have changed since her courting days, and the losers and playboys outnumber the eligible and willing bachelors. As the miles roll by, their journey veers from eccentric, to poignant, to comic.