Based upon a story by actress Jennifer Jason Leigh who also had a bit part to lay here, and directed by Noah Baumbach who share screenplay credits, Greenberg is a tale that deals with the anxieties of the 40 year olds who are starting to wonder how half their lives had passed them by without anything to show for, and how much courage they have to try and reinvent themselves for the remaining half. Usually at a mid-life crisis, one would find a certain itch to want to break away from the norm and routine, but scratching that itch would depend on how severe it is, and how hungry one actually is in wanting to embark on change and do something different.
Despite its title being the last name of its male protagonist, Greenberg opens with a typical day in the life of Florence Marr (Greta Gerwig), the ever capable personal assistant to the Greenberg family headed by Phillip (Chris Messina), and because this part of the Greenberg family is heading to Vietnam for a vacation, Phillip's brother Roger (Ben Stiller) decides to move in temporarily from New York to Los Angeles for 6 weeks in order to do nothing, and in return for his brother's provision of a roof over his head, Roger's carpentry skill will be called upon to build a doghouse.
But this film is not about showing off his carpentry skills, but more of how he builds up new relationships with the household mutt, and Florence to whom he has taken a strange fixation and fancy to, while on the other hand still holding a candle for his ex-flame Beth (Jennifer Jason Leigh). And having just come out of a mental institution for a psychological issue didn't help either, as we see how temperamental and volatile Roger can get, where relationships he built with such difficulty, can be utterly destroyed at his uncontrollable blow ups.
In a way, this film is quite the depressing one, where folks like me and of course the older generation, may feel some pangs in wondering, like Roger, how we ended up the way we are, and the contemplating of the What Ifs and missed opportunities from relationships and family, to friendship and that of a professional life which could have possibly lifted Roger to fame and fortune, if not for his inexplicable rejection of that single chance that could have changed his life for the better. For the optimistic, this will be a strange film to sit through, as there's very little uplifting moments. Heck, even the door falls sick to some little known disease, and many faceless characters come and go without having any emotional resonance with Roger.
Which makes him yearn companionship in whatever means possible, even if it means sleeping with, or trying to, with his brother's assistant Florence, who somehow likes Roger for the very low key way of leading his life built on the basis of doing nothing, without the pressures of expectations, or imposing one's will on the other. Wait, scratch that last point, as Roger does make their friendship/relationship complex no thanks to not knowing what he wants, and not admitting things he desires. This forms the basic anchor for the film to develop upon, with commentary during a house party filled with youngsters about the impetuousness of youth, and the rather throwaway lives they lead with the drinking and drug abuse, and the lack of responsibility in clearing up the mess they leave behind.
It's a refreshing change to see Ben Stiller in a non comedic role, where he plays serious for once, and showcase some dramatic chops. Paired opposite him is Greta Gerwig who managed to hold her own as Florence, who's top notch at organizing other people's lives, but really zilch in looking after her own interests, succumbing to sex with strangers as a relief of sorts. Despite the nice casting in Greenberg, this indie film is not an easy one to sit through, not appealing to the depressive since its themes are quite the downer, and neither gaining fans from the optimistic since they'll likely be in deep thought once the show ends. But endure and stay for the top notch performances, with a proper, well deserved payout waiting for you right at the end of it.