October 17, 2025
Let’s talk about her incredible authenticity. Keaton had a remarkable quality in that she never tried to be anyone but herself. In an industry that constantly pressured women to conform, she maintained a quirky, individualistic persona throughout her entire career.
Whether she was on screen or doing interviews, a sense you were seeing the real her…nervous tics, scattered thoughts, and all. That vulnerability was endearing.
Her style was iconic for a reason. The whole menswear-inspired aesthetic she popularized…oversized blazers, ties, vests, wide-legged trousers, wasn’t just a costume choice. It became part of her identity. Hepburn-like (another authentic star). She took something unconventional for women at the time and made it sophisticated and cool. Even in her late seventies, she was still rocking turtlenecks, hats, and gloves with an effortless elegance. She never apologized for dressing differently, and that confidence was inspiring.
What really made Keaton special was her comedic timing. Watch her in Annie Hall and you’ll see someone who could make stammering and awkwardness hilarious without it ever feeling forced. She didn’t go for the obvious laugh. Her humor was observational, self-deprecating, and incredibly smart. The way she delivered Woody Allen’s dialogue…with those “la-di-da” moments and nervous energy…created something entirely new. She won the Oscar for that role, but beyond the award, she created a character that felt like a real person, not a punchline.
But she wasn’t just a comedic actress. Her range was extraordinary. She could do romantic comedy brilliantly, as we saw in Something’s Gotta Give where she held her own against Jack Nicholson. She could do drama…look at The Godfather films where she played Kay Adams with strength and moral clarity. She could even do psychological thriller, as in Looking for Mr. Goodbar. Not many actresses could move between genres so seamlessly.
There was also something really likable about how she aged in Hollywood. She was open about not having plastic surgery, about embracing getting older, about wearing turtlenecks to cover her neck because that was what made her comfortable. In interviews, she talked about her insecurities, her dating life, her choices. She adopted two children as a single mother in her fifties, which was unconventional at the time. She lived life on her own terms.
Her relationships with directors and co-stars spoke volumes too. Woody Allen wrote Annie Hall specifically for her, inspired by their real relationship. Warren Beatty, Al Pacino, Jack Nicholson…she worked with some of the biggest names and by all accounts, they adored working with her. She brought out something special in her partners. There was a generosity in her performances… she wasn’t trying to steal the scene; she was trying to make the scene work.
Her self-deprecating humor in interviews was delightful. She’d talk about being nervous, about feeling inadequate, about her various obsessions and anxieties. It was refreshing because it was honest. And we could all relate. She didn’t pretend to have it all figured out. At one point she described herself as “a whirling dervish of a woman” and that kind of summed up her energy…chaotic, enthusiastic, always moving, always feeling things deeply.
The fact that she stayed relevant across multiple decades was remarkable. She was huge in the seventies when I knew her work, continued strong through the eighties and nineties, then had an incredible resurgence in the 2000s with Something’s Gotta Give. She was one of those rare actresses who was interesting at every age, playing age-appropriate roles that showcased different aspects of her talent.
Maybe what was most likable about Diane Keaton was that she made being yourself seem not just acceptable but actually cool. She showed that you didn’t have to fit into a conventional mold to be successful, beloved, and considered beautiful. She was neurotic, funny, talented, stylish in her own unique way, and unapologetically herself. In a world that often demanded conformity, especially from women, that was pretty wonderful.
Back in the day, when I was in college, I can assure you that every guy in every dormitory, fraternity and sports team was in love with Diane Keaton. Me too. I think her work in Love and Death, Woody Allen’s send up of Tolstoy’s War and Peace was wonderful. And as a fan of Russian Literature, I’ve watched it over and over through the years. The jokes are clearly geeky, but so much fun.
I eulogize Ms. Keaton here in part because she represents so much of what Hollywood, and entertainers could be, but increasingly are not. First, entertainers, then, interesting and fun, and finally, true to their own lights but not with brawny and hungry egos needing to be constantly fed.
Like Rodney Dangerfield and Robin Williams and John Candy, she joins the ever-increasing list of the wonderful people who inhabited my younger years, who illuminated daily life and made me laugh and feel good about the world, no matter how difficult the world had become.
I regret her passing very, very much.
I think for anyone my age, a piece of us went with her.
In part, I think that’s what we also mourn.
Thoughts, questions, or reflections? I’d love to hear them. You can reach me anytime at anthony@workingprofit.com
