Updated: March 10, 2023
Still Need to Watch: Please Give
Nicole Holofcener specializes in empathetically capturing the loves in self-involved upper middle class whites stuck in a bubble and going through it. No one going today is able to explore stuff like that and make you it seem so true to life.
5. Friends With Money 
On the surface, this film is about the seven most intolerably annoying white people that ever lived. In reality though, they are simply terribly unhappy with their meaningless lives and as a result, they are intolerably annoying. The children of “the greatest generation” grew up and basically became gigantic life-hating losers who somehow came to value all the stupidest things and gave up on caring about anything. There was something undeniably true to the experiences and interactions explored in this film. That deep unhappiness that leads to completely irrational cruelty is just so common and so miserable to witness. The accuracy in which the film captured that sensation at times made this a painful watch.
4. Lovely & Amazing 
Going back and watching an early Holofcener was pretty fascinating. You get an early glimpse at what things she would explore throughout her career and what are ideas she would either abandon or grow less interested in.
A big constant of Holofcener is that is drawn to crafting characters who are, to be reductive, awful. They are self-involved people stuck in a bubble and going through it. And that is a recipe for selfishness and running people over.
A big way she has always captured that is by showing these characters use and take advantage of young people’s desire for approval. In this film, Catherine Keener has an early onset midlife crisis and starts to fuck a 17-year-old (Jake Gyllenhaal!).
I must confess that it was refreshing how this sexual relationship was portrayed in that it played out in ways that felt like how human beings (to the extent you can call a teenage boy a human being) would respond to the situation. Keener is lost and unsatisfied with her life in every way. Jake is a puppy dog looking to please and to feel older and cooler. In every way Keener is taking advantage of him even if Jake is willfully and gleefully taking part. The relationship is wrong and irresponsible, but the film doesn’t need to excuse Keener for doing it just because she is the POV character.
3. Walking and Talking 
To go back and watch Nicole Holofcener’s first feature-length film was such a joy. You get to see some ideas she has always explored and some ideas that will be present in the future but were not yet on her mind (apparently).
Catherine Keener and the people in her life are in their twenties and absolutely lost. Her best friend (Anne Heche) has settled down with her longterm boyfriend (Todd Field) and are set to get married. Heche is struggling to accept that she is about to give up any sense of freedom. Field is at a complete loss for how to balance being content while still looking for ways to be passionate and exciting. Her ex-boyfriend (Liev Schreiber) is struggling with how to be selfish in a way that does not run over other people. Keener’s relationships with all of them (particularly Heche and Schreiber) are at various levels of fraught due to the general level of mental and emotional change in all of them.
The film deftly captures the utter chaos of being in the transition period before you’re a fully mature adult. The constant tension for the desire of stability with the desire of freedom to explore. Young longterm friendships evolve. Your jobs either suck or starting to become careers. The line between relationship and friendship somehow gets messy for so many of us. We have no idea how to prioritize our own needs without being dicks to others. We can be just so fucking annoying without meaning to be as we try to figure out our shit. It fucking sucks. And Holofcener shows it all with her trademarked empathy and honesty.
2. The Land of Steady Habits 
We join the story a few months into Ben Mendelsohn’s “midlife crisis” (to be reductive). He has thrown away his finance career and his marriage to Edie Falco. He has caused a strain in his relationship with his son and the community in their suburban town. The film then tells the story of Mendelsohn way too slowly coming to terms with the fact that it is him that is broken and sad and unwell and the source of his own unhappiness.
Holofcener has one of the sharpest eyes for capturing the problems of upper middle class white suburbia and how those problems speak to larger issues and call for questions. She is also uniquely talented at showing human beings at their worst and making them relatable and understandable. How do we become so self-involved and self-destructive? What causes us to lose empathy for those around us, especially the ones we are supposed to love the most?
1. Enough Said 
While there is a lot to talk about here, the part that will always mean the most to me is getting to watch James Gandolfini in one of his last film roles. While he will always be first thought of as Tony Soprano, it is clear that it is actually this film that most accurately captures his natural charms. The way he can simultaneously display so facets of himself in a completely authentic manner was just remarkable. Gandolfini was effortlessly able to the sweet, gross, intimidating, vulnerable, and a whole of qualities that always helped to make him undeniably human on screen no matter what he was acting in. Rarely though, did any film or show allow him to use that part of himself to just be a regular guy. It was quite beautiful to watch.