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Miles Raymond, a failed writer and divorcé who teaches junior high school English takes his best friend, former hot actor Jack, on a weeklong drive up to California’s wine country. There they explore the nature of their failures and question their relationships. Jack, about to get married, has an affair with a woman and wonders whether he should call off his wedding. Miles questions whether or not he made the right choice while trying to form a relationship with the woman’s best friend, a fellow oenophile who is a waitress at a restaurant that he frequents often when visiting that part of the country.

This film charts the rise and fall of Yuri Orlov, from his early days in the early 1980s in Little Odessa, selling guns to mobsters in his local neighbourhood, through to his ascension through the decade of excess and indulgence into the early 90s, where he forms a business partnership with an African warlord and his psychotic son. The film also charts his relationship through the years with his younger brother, his marriage to a famous model, his relentless pursuit by a determined federal agent and his inner demons that sway between his drive for success and the immorality of what he does.