We don’t see Rob Greenberg, the nebbish, narcissistic, mentally-ill man child, until maybe the first 10 minutes or so of the movie have passed by. Prior to then, everyone else who will be later sucked into Greenberg’s toxic web of paranoia and bad vibes is cozily going about their day. His brother and sister are packing for a vacation, and their assistant Florence (Greta Gerwig) is crossing off boxes on her daily to-do list for the family. Florence isn’t necessarily unhappy as she is confused, she isn’t distraught with serving a family day after day, it’s just that she doesn’t know what she’d rather be doing instead.
Then Greenberg shows up. Like a splinter stuck underneath your pinky fingernail, Greenberg is a nuisance and a pain whom others must deal with before he eventually leaves LA back for New York. He’s an immensely obnoxious, completely unlikable character, one who takes us on a journey of mostly disgust and remorse and sometimes pity. Anyone who still holds a grudge against their selfish friend from high school or a rude, improper roommate will feel a strange catharsis anytime Greenberg is told off. And anytime Greenberg tells someone off or makes one of his dozen social faux pas, we’ll find ourselves first judging him, then pitying him, then sadly, seeing a bit of ourselves in him.
It’s a remarkably fascinating character exercise, made possible by its loose-leaf plot and the film’s honest, raw dialogue. Gerwig is fantastic as the confused Florence, showcasing the actress’ ability to bring soft-spoken characters like Florence to life just as much as her more confident, boisterous roles in Frances Ha, 20th Century Women and Mistress America. But the real star is Stiller, an actor whose spent so much of his career playing the likable but concerned lead in rom-coms and now just plays a strange, satisfying mix of overly-concerned and not-concerned-at-all. At the end, we’re happy to see Greenberg go from our lives, but we’ll never forget the time we spent with him.