Awhile back, I boldy claimed (in my review of Tropic Thunder) that Ben Stiller was a modern-day Mel Brooks. The analogy was never precise, and with Greenberg, Stiller plays a dead-on jaded sad sack in a style Brooks never even attempted. He's only funny when you're laughing at him for being so incapable of just letting go (which is all he says he wants). He's aggravatingly impatient and discontent. Astonishingly (and to his credit), Stiller totally disappears in this maladroit character.
Maybe this stylistic departure is to be expected; after all, this isn't a Ben Stiller movie, it's a Noah Baumbach movie. I don't think it's too early to say that Baumbach's speciality is tales of amusingly uncomfortable assholes struggling to be better (see: The Squid and the Whale, The Life Aquatic, even Fantastic Mr. Fox). With Greenberg, this trope is taken to a new extreme: the movie is ALL about the asshole, in what ways he is damaged, and who he disappoints. For me, it was a little too much asshole.
Part of the problem may be the relative sweetness and relatability of the main person Greenberg is affecting, Florence, played by the refreshingly natural but still beautiful Greta Gerwig. I like to imagine that I have some hip-kid claim on knowledge of Gerwig, because I saw her in Joe Swanberg's Hannah Takes the Stairs in 2007 (the film was shot in Chicago, and I kind of know Swanberg, so I win, right? Right??). Gerwig is precious and likeable in Greenberg, and despite Florence's fondness for its main character, the script doesn't keep us from liking her. But Florence's desire to "save" the damaged Greenberg, and her affinity for his quirkiness, doesn't totally rub off on the audience, nor does the patience his friend Ivan (Rhys Ifans) constantly showers on him.
Cinematically, Greenberg is oddly reminiscent of a New-Wave French film or even Italian Neorealism. No, seriously. We watch characters stare at each other in silence, unsure of what to say. The palpable awkwardness of a conversation between Greenberg and an old girlfriend (Jennifer Jason Lee) seems plucked from real-life, and the amount of time the cast spends dealing with the sick family dog will feels real and familiar. It's both fascinating and annoying to jump from scene to scene without knowing what has happened in between.
If my take on Greenberg seems a little harsh, it's because there is much to love about the film: its wry humor, the quietly unfolded backstory of the characters, the genuine pathos of growing older that each handles in a different way. This is what makes it so frustrating that the events of the film are steered by such an unlikeable (but well-acted! Ugh!) character. If the movie were bad, it would be easy to accept such a major flaw. instead, the plusses and minuses of Greenberg war with each other and with me. Perhaps Greenberg himself said it best in his letter to Starbucks: "…you have been surprisingly successful for the most part. The part that isn't covered by 'the most part' sucks."