Chicago subway worker Lucy (Sandra Bullock) is infatuated by businessman Peter (Peterg Gallagher), a commuter who regularly uses her station and who she only ever sees from a distance. One day, Peter is almost hit by a train, but Lucy manages to save him at the last moment; then, as she sits by his side while he lies unconscious in a hospital bed, his family arrive and mistake her for his new girlfriend. Happy to be welcomed into the home of her dream partner, Lucy tries to gather the strength to set the record straight, but the situation only becomes more complicated when she starts falling in love with Peter's brother Jack (Bill Pullman).

Bruce Robinson writes and directs this drama based on the debut novel of Hunter S. Thompson. Johnny Depp, who also co-produces the film, stars as burned-out vagrant freelance journalist Paul Kemp, who leaves his life in New York behind and heads off south to work for a local newspaper in San Juan, Puerto Rico. There he adopts the debauched, liquor-soaked lifestyle of Hemingway's 'Lost Generation' and develops an unhealthy obsession with Chenault (Amber Heard), the beautiful fiancee of shady property developer Sanderson (Aaron Eckhart).