I once posited there’s no Greta Gerwig and “Ladybird” without writer/director Nicole Holofcener, and I still believe that to be true. For three decades, Holofcener, the indie filmmaker behind cult feminist comedic indies like 1996’s breakthrough film “Walking And Talking,” 2001’s “Lovely & Amazing, 2006’s “Friends With Money”—featuring a semi-rare indie acting turn for Jennifer Aniston— and many more, has been delivering sharply observed, bitingly hilarious, empathic, complex comedies about the human condition, family, and life’s ordinary struggles. While her various neurosis had been often compared to Albert Brooks, Woody Allen, Walt Stillman—makers of somewhat similar urbane and anxious comedies—Holofcener’s unique and thus so is her very emotionally autobiographical work.

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There’s great sarcasm, self-deprecation, shame in the comedic side of her work. The humane part is filled with guilt, resent, compassion, love, and altruism, and to that end, at the heart of many of her films is the central human idea of selflessness vs. selfishness, that struggle, and how the two ideas can co-exist. Whether it’s the well-meaning mom (Brenda Blethyn) in “Lovely And Amazing” that adopts a child for potentially selfish reasons, or the conflicted and compassionate New Yorker (Catherine Keener) in “Please Give,” who loves her neighbor but is also waiting for her to die so they can expand their Manhattan apartment, Holofcener is fascinated with the innate contradictions of human beings in the ways it makes for lacerating comedy, but also the sometimes sad and depressing commentary on people.

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Nuanced and funny portrayals of flawed, complex women whose outward sophistication belies their dysfunctional, often disastrous personal lives is her bread and butter and recently, just last month, the streaming Criterion Channel made three of her classic films available, “Lovely & Amazing,” “Friends With Money” and “Please Give” (2010). All three of these dramatic comedies—all of which employ her muse, Catherine Keener—demonstrate her ahead-of-the-curveness when it comes to ideas of privilege, wealth, social inequality, and class interwoven with stories about family. “Please Give” is a darkly funny satire of self-involved white liberal guilt, “Friends With Money” is a cutting class comedy, and “Lovely And Amazing,” while more of a family drama about sisters and the legacy of our mothers, still has plenty to say about privilege, shallow concerns, and human folly. I spoke to Holofcener late last month, during the height of COVID-19, but before the Black Lives Matter protests, for context. We dove in about the complexity of her characters and stories, and we even spoke a little about her co-writing gig on Ridley Scott’s next movie starring Ben Affleck and Matt Damon.

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Your films, especially this trio on Criterion— there’s always this wonderful and hilarious mix of altruism, narcissism, even mean-spiritedness, that goes together in this terrifically comedic, but also very human and real way.
I think it all goes together, those contradictions, right? I’m not mean spirited, but certainly, a kind and empathic character might be dull, without the selfish narcissism side of things, because we’re human. It’s unavoidable to have some of that even in a fully mature person. My own empathy or sympathy sometimes is self-involved. Like, look at the characters in “Please Give,” she can’t volunteer without falling apart, and how useless that renders her. And sometimes that has happened to me, although I have found ways to volunteer where I’m not as emotional or tragic [laughs].

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Like, we were talking about COVID-19, and people are dying, and the world is changing. But I also tried to put in an order on Amazon Fresh the other day and I’m annoyed I can’t get what I want. But at the same time, I can’t actually hug my mom. Meanwhile, people are dying. Meanwhile, I ordered a rug the other day, like, Do I not order the rug? Is now not the time to order the rug? Should I not buy it? Should I not even want it? So, it’s all those kinds of things and contradictions that really interest me in people, myself, my characters. Look, I’m frequently filled with shame.

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Yes, there’s so much shame and guilt in your films! It’s very funny, and at the same time, so tragic in ways too.
I think shame is a huge part of everybody’s life and path.

Well, if you’re a certain type of person. I mean look at Trump, the GOP and some of those many grifters in the orbit of the White House, they’re all pretty shameless.
Yeah, no kidding. That’s a perfect word. They’re shameless. I can only hope these crazy non-mask-wearing Trump supporters, are deeply disturbed and suffer because they are shameless. And then there’s us, the good folk [said sarcastically and self-deprecatingly], wanting to take care of the world, but are filled with shame and regret.

I’m not supposed to wish bad things on bad people, but I do.

[Laughs] Well, if it makes you feel any better, I definitely wish for horrible shit on these grifters [laughs]. It strikes me that your work is not only autobiographical, but like emotionally autobiographical. Like Francis McDormand just beside herself at the rudeness of someone budding in line in front of her at Target in, “Friends With Money.” That feels like it’s written from you in a cathartic perspective.
Oh yeah, Francis embodies me, the part of me that’s a warrior for justice and basic fairness. I think me wishing bad things on bad people is similar. I’m not wishing bad things on ex-boyfriends or people who hurt my feelings. I’m talking about the people who are ruining this country. Like really awful people. So that’s part of it. Even though I have such a privileged life— I would say one in general often feels cheated nevertheless, even if it’s on a small human level like that, and sometimes we don’t know what we feel cheated from. That character certainly has nothing to complain about yet, when you think of her privilege and wealth. But she’s getting older and she’s depressed and she’s angry she feels like it’s not fair. She’s fighting against nature.

I want to yell at everybody to put on a mask, but I’m afraid to get shot. So that would be my current version of being a warrior for justice and fairness. Do I sound crazy, am I making sense?