Grosse Pointe Blank (1997)

John Cusack stars as Martin Blank, a freelance assassin facing a crisis of conscience. Back home for his 10th anniversary high school reunion, Blank must fend off a professional peer (Dan Aykroyd) dead-set on inducting him into the newly formed assassins union, sort out his feelings for his high school sweetheart (Minnie Driver), and squeeze in a last-minute contract killing.