You probably know someone like Greenberg, a guy who had a band in the '80s that was this close to making it, and who never really amounted to much, but whose self-loathing is only matched by his general feeling of superiority to almost everyone he meets.
What you might not expect is that they’d make a movie about that guy, and then actually have the audacity to make him the (anti)-hero. But that’s just what master of misery Noah Baumbach (The Squid and the Whale) does.
Roger Greenberg (Ben Stiller) has just been released from a mental hospital after a nervous breakdown and he’s spending some time in L.A. house/petsitting for his brother, a successful businessman. Greenberg is now a carpenter, he works out of a co-operative studio in New York. “It’s very political,” he mutters at one point. (In that single line, we sort of get all we need to know about Greenberg’s life as a carpenter in New York—that he rationalizes his own lack of success by asserting that the system is political. He probably figures that the other carpenters don’t like him because they’re jealous of his talent, not because he’s a dick.)
Greenberg decides it's time to give up his life of semi-employment for one of righteous unemployment, a great way to turn his floundering into a kind of philosophical statement. (He also believes that he’s building a dog house for his brother's German Shepherd out of some sense of altruism, not because his brother is providing him with a free room and board.)
Luckily, Greenberg is just convincing enough about his own lofty intentions to dupe others, especially the impressionable and somewhat doormaty 25-year-old Florence (Greta Gerwig), his brother’s personal assistant. Florence develops an ill-advised crush on the 41-year-old Greenberg, who still obsesses over his ex-girlfriend (Jennifer Jason Leigh, Baumbach’s wife and collaborator), who has completely moved on with her life.
Greenberg also has a best friend (Rhys Ifans), a recovering addict named Ivan, who used to play in the band with him. Greenberg is such a narcissistic jerk that he keeps offering his recovering friend a drink (whoops! he forgot!) and also doesn’t bother to remember the name of Ivan’s son. He’s rooting for Ivan’s marriage to fail—he tells himself its because Ivan’s wife once made a racist comment in front of him—but it’s truly because he wants Ivan to be as miserable as he is.
Greenberg is a movie that is funny-insightful and funny-sad and sometimes just flat out funny. It also has a major find in Greta Gerwig, who brings a soft-focus, sexy sweetness to the role of Florence. And it’s a tribute both the talent of Stiller, who dials down the jokey stuff to give a measured, mature performance, and that of writer/director Baumbach, that we find Roger Greenberg tolerable and maybe even root for him (well, at least a little).