Just as he's turning forty, Roger Greenberg (Ben Stiller) finds himself with no real friends, no significant other, and no actual purpose in life. He's also just been released from a mental institution, so you can well imagine that his neuroses are going to be pretty much off the chart as well. A carpenter and former musician who regularly resides in New York City, Greenberg is currently house-sitting at the Hollywood Hills home of his wealthy and successful brother, Phillip (Chris Messina), while the latter is away on business in Vietnam with his family. While he's staying there, Greenberg meets Florence (Greta Gerwig), a sweet but rather unfocused woman almost half his age, who works as a personal assistant – i.e. dog walker, babysitter and all-around gopher - to Phillip and his family.
Greenberg's mental issues manifest themselves through various phobias and idiosyncrasies, all of which lead us to the conclusion that he is generally just afraid of life, of taking a risk when doing so could possibly lead to failure. To that end, he avoids large groups of people, writes endless letters of complaints to companies he feels have somehow screwed him over, overreacts to other people's words and actions, and makes a general antisocial and sociopathic pain-in-the-ass of himself. And to no one is he more psychologically abusive than to Florence, a girl with her own share of vulnerabilities, who in his own crazy way he is obviously trying to impress but who he just keeps pushing away with his eccentric behavior.
It's hard to really get much of a bead on either Greenberg or Florence, and that is both the greatest strength and the greatest weakness of the screenplay by Jennifer Jason Leigh and Noah Baumbach, who also directed the film. On the one hand, one appreciates the complexity of the characters, their refusal to allow themselves to be pigeon-holed into one neatly delineated box or other. On the other, the coolly objective stance the script takes creates a barrier between us and the characters, the result being that we find it hard to identify or empathize much with them, especially Greenberg, who finally becomes as off-putting to us as he is to those he comes in contact with throughout the course of the picture. In drama, there's a fine line between a character who is intriguingly different and one who is just annoyingly self-indulgent, and "Greenberg" crosses over that line with dismaying regularity.
Still, the performances are excellent – this is probably Stiller's best dramatic work to date – and the inconclusive ending is impressively brave enough to erase a multitude of earlier sins.
