Charlie Mayeaux (Liam Neeson) is an undercover DEA agent suffering from anxiety and gastrointestinal problems after a bust gone wrong. During the aforementioned incident, his partner was killed and he found himself served up on a platter of watermelon with a gun shoved in his face just before back-up arrived. Charlie, once known for his ease and almost “magical” talent on the job, is finding it very hard to return to work. His requests to be taken off the case or retired are denied by his bosses, Lonny Ward (Louis Giambalvo) and Dexter Helvenshaw (Mitch Pileggi) as so much time was put into his cover. Charlie works with the dream of one day retiring to Ocean Views, a luxury housing complex with servants and utilities.
During his flight to New York, where his job will resume, another passenger strikes up a conversation with him. It turns out that this man, Dr. Jeff Bleckner (Michael Mantell), is a psychiatrist and upon arriving to New York, Charlie enlists his services. Dr. Bleckner listens to his troubles and prescribes him anti-anxiety medication to help him deal with stress. He also encourages him to join a group therapy session. At therapy, Charlie meets and befriends a group of stressed out men from the business world.
To deal with his gastrointestinal issues, Charlie goes to the doctor where he meets the free-spirited and beautiful Judy Tipp (Sandra Bullock), the self-proclaimed “Enema Queen” who introduces him to alternative therapies to his problems as well as some romantic interest.
Back on the job, Charlie is knee-deep in negotiations for high-stakes money laundering and stock manipulation. He was brought into the group by the passionate Fidel Vaillar (José Zúñiga) and his close bodyguard, Estuvio Clavo (Michael DeLorenzo). Vaillar is a son of an important Colombian druglord and fears being viewed as a stereotype. They are dealing with an intense man with an unpredictable temper named Fulvio Nesstra (Oliver Platt) who represents the Italian mob in New York. Fulvio is the disfavored son-in-law of high-ranking Italian mobster, Carmine Minetti (Frank Vincent). Jason Cane (Andrew Lauer), a young Wall street-type with a plan, but poor taste, completes the group. Each thinks he understands the other players, but there is more to these characters than meets the eye.