Ben Stiller stars as Roger Greenberg, a lonely fortysomething from New York who has just flown out to Los Angeles to housesit for his rich brother, who's off with his family on a working vacation in Vietnam.
Roger arrives with some serious baggage: back home he suffered a nervous breakdown and was committed to an institution for a while. That doesn't seem to matter much to Florence (mumblecore "It" girl Greta Gerwig), the family's personal assistant, who takes an inexplicable shine to the troubled Roger. And so a tenuous relationship ensues, one that could only be doomed by Roger's awful behavior.
Noah Baumbach seems to have found his niche in chilly dramas about dysfunctional and profoundly unlikable characters (The Squid and the Whale, Margot at the Wedding) and Greenberg is more of the same. The performances are fine – anyone expecting a silly Ben Stiller comedy will not get what they came for; as I've avoided most of those comedies, and still remember the actor from his straight roles in Reality Bites and Zero Effect, I have no problem accepting him in a dramatic part – and Baumbach does a good job at capturing the Los Angeles of 2009.
Gerwig's character is another so-called "manic pixie dream girl", like Natalie Portman in Garden State: the quirky, cute, always-available young woman who falls for the protagonist, no matter how much of a loser he is. And there is no question that Stiller's Greenberg is one big loser. But Baumbach wrote the story with his wife, actress Jennifer Jason Leigh (who also coproduced and costars), and she knows something about strong female characters. So the film also shows that fun hipster chicks can feel sad and empty as well: Florence has a drab apartment, a weak personality, and a gloomy secret of her own. If she finds something to love about a man fifteen years her senior, who has so little to offer, it's not that hard to swallow since she's not really that much of a catch.
As for Stiller, it's not hard to imagine that this angry, neurotic, self-absorbed character may be closer to the real Ben Stiller than most of his other roles. I should also mention terrific supporting work from Rhys Ifans, playing Roger Greenberg's old friend and former bandmate.
There are lots of nice character details in Greenberg, but I can't say that it's an enjoyable or satisfying film. As a man around Greenberg's age, dealing with the same issues of arrested development when everybody else my age seems to be making money, buying houses, and having children, I should identify with him at least to a degree. But I've never been able to connect with Baumbach's caustic characters. Maybe that means I'm healthy, or maybe Baumbach's characters are not that true to life.