One of the primary concerns of the movie is the portrayal of love and relationships in the modern era. Jamie and Maggie's relationship is authentic and passionate, but it's also complicated by their individual struggles. Jamie is struggling with the moral implications of selling a drug that is often overprescribed, while Maggie is dealing with the physical and emotional challenges of her illness. Their love becomes a refuge for both characters, but it's also fraught with uncertainty and vulnerability.
| Actor | Character | Description | | :--- | :--- | :--- | | | Jamie Randall | A talented but superficial pharmaceutical salesman and womanizer whose charm is his greatest professional and personal asset. Over the course of the film, he is forced to grow up when he falls in love. | | Anne Hathaway | Maggie Murdock | A sharp-witted, free-spirited artist with early-onset Parkinson's disease. She avoids long-term relationships to maintain her independence and to protect herself and others from the progression of her illness. | | Oliver Platt | Bruce Winston | Jamie's veteran and cynical mentor at Pfizer, who is eager to get off the road and provides Jamie with crucial, albeit rough, training in the pharmaceutical sales game. | | Hank Azaria | Dr. Stan Knight | A sarcastic and pragmatic doctor who becomes one of Jamie's most important clients. Azaria brings a dry wit and moral ambiguity to the role. | | Josh Gad | Josh Randall | Jamie's wealthy and supportive brother, who uses his connections to help Jamie get his foot in the door of the pharmaceutical industry. Gad provides much of the film's comedic relief. | | Gabriel Macht | Trey Hannigan | Jamie's slick and ruthless corporate rival, who is consistently one step ahead in the sales game. Macht portrays the film's antagonist with effortless charm and aggression. | | Judy Greer | Cindy | Maggie's grounded and loyal sister, who is often the voice of reason and cares for Maggie's well-being. | | George Segal | Dr. James Randall | Jamie's respected father, a doctor who is disappointed by his son's lack of direction and moral compass. | | Jill Clayburgh | Nancy Randall | Jamie's supportive mother, who sees the good in her son and encourages him to find himself. |