Movies like Things to Do in Denver When You're Dead

Jimmy the Saint's business is videotaping the terminally-ill, so that they will be around to give 'Afterlife Advice' to their survivors. He hasn't been doing too well lately and has had to turn to loan-sharks to accomodate his failing business, as well as his expensive personal tastes. When an evil gangster-overlord buys up his note and demands a favor of Jimmy, in exchange for the interest that he can't afford, Jimmy capitulates. Jimmy is to scare someone for the gangster-overlord--really rough them up. Without giving too much away (spoiler), the scene goes down badly and Jimmy and his crew all end up with contracts on their heads for their trouble.