Grosse Pointe Blank (1997)

Plot: Martin Blank is a contract hit man. After being in the business for five years, he is getting disillusioned with it, imposing himself on a therapist, Dr. Oatman, who is reluctant to help him through his issues because of his business. Part of his disillusionment is because of the changing nature of the business, as witnessed by one of his fellow hit men, Grocer, wanting to form a cartel of sorts despite the inherent non-trust with each of the other hit men. Because of one of his contracts not having gone down quite according to plan, Martin is forced to take a job in Detroit for the same client pro bono. Marcella, who handles the administrative aspects of Martin's business, encourages him to attend his ten year high school reunion in Grosse Pointe in suburban Detroit while he's there anyway. Martin left Grosse Pointe the day of the graduation prom never having returned. In the process, he stood up his prom date and serious girlfriend at the time, Debi Newberry. While in Detroit/Grosse Pointe, Martin wants to forget about his hit man life and focus most specifically with reconnecting with Debi, who now works as a local radio host. Making it up to Debi may not be as easy as Martin wants, despite both still being attracted to each other. But getting away from his hit man life may not be that easy either as Grocer has tipped off the NSA to Martin's job, the two agents, Steven Lardner and Kenneth McCullers, who plan to take him in when they catch him in the process of the hit, but who contemplate taking him out themselves. In addition, Martin learns the hard way that someone else has taken a contract out on him. Martin's life becomes even more complicated when he learns who his contracted hit is.