Everybody needs a mentor. Unfortunately, when you're a recent transplant to suburban Virginia who's not quite fitting in at your new prep school, options may be limited. For example: the terminally ill, ex-CIA assassin who lives next door, as is the case in Tony McNamara's darkly charming Ashby.
Ed Wallis (Nat Wolff) strikes up the acquaintance of Ashby (Mickey Rourke, doing his Marv-from–Sin City voice) when assigned an "interview an old person" essay. Ed soon discovers his subject is not the napkin salesman he claims (and really, one assumes a professional killer could come up with a better cover). The two enter a kind of symbiosis, Ed inadvertently nudging Ashby into making amends and the old spook bluntly encouraging Ed to reassess certain realities.
Ashby could easily have gone too far into maudlin or hostile territory, but McNamara maintains the right approach, treating even unpleasant topics, like absentee parents and chronic traumatic encephalopathy(!), with a light touch, recalling other coming-of-age black comedies like Heathers. It doesn't hurt to have excellent support from the likes of Emma Roberts (as Ed's love interest Eloise) and Sarah Silverman, surprisingly winning as Ed's affection-starved mother.
But it's Wolff and Rourke who have to carry the load, and for the most part they do. Wolff is easy to root for, portraying Ed with refreshing complexity. Rourke is more uneven, but generally captures the discomfort of a person unaccustomed to giving advice, and is definitely a good choice for teaching someone how to roll with life's punches.