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John Lyshitski is a car stealing slacker, with a weed problem, and has been in Illinois’ Rossmore State Penitentiary so many times, he knows it’s entire population of both staff and cons by their fast names. Cursed with the old ill luck of being in the wrong place, at the wrong time, in possession of the wrong car, he’s been deemed a lost cause repeat offender in the eyes of everyone else. When the heartless judge, who has been behind most of his sentences, goes to the big court house in the sky, John decides to ruin the man’s legacy by having the judge’s only offspring, Nelson Biederman IV, thrown in the slammer along with him. Here, the world-class selfish jerk learns a certain old lesson the hard way: Do unto others as you would have others do unto you. But has John somewhat gone too far in the payback department?

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.

Tim Kearney is an incarcerated former Marine who is offered freedom by DEA agent Tad Gruzsa in exchange for impersonating recently-late drug lord Bobby Z. Things don’t go as planned, however, and Kearney ends up on the run with Bobby Z’s 12-year-old son.