The Curious Mind and Singular Success of Diane Keaton

In the spring of 1972, Play It Again, Sam and The Godfather were released six weeks apart. “After that, things were different,” Keaton admits. She was on her way.

Her Oscar for Annie Hall followed six years later, when her affinity for oversize menswear and floppy hats sparked a trend. That film was followed by decades of comedies and a few dramatic roles, including Reds and Marvin’s Room, both of which earned her best actress Oscar nods. (Her fourth nomination was for writer-director Nancy Meyers’ Something’s Gotta Give.)

Last August, Keaton stuck her hands in wet cement as part of a ceremony to place her handprints and footprints at the TCL Chinese Theatre. Choking up during her speech, she dedicated the moment to her parents.

On Valentine’s Day this year, Keaton posted a montage of some of her steamiest make-out scenes, dedicated to “all the men who were paid to kiss me.” (Responded Meyers: “Hilarious but as someone who was around for a few of those — those guys always wanted one more take.”)

The actress has had several high-profile romances in her life, including with Woody Allen, Warren Beatty and Al Pacino, but she has never married. Today, she declares, she is happy on the shelf.

“I don’t date,” she says. “Highly unlikely. I don’t remember anyone calling me, going, ‘This is So-and-So. I’d like to take you out.’ They don’t happen. Of course not.”

Photo by: RUVEN AFANADOR

But Keaton didn’t allow the lack of a partner to keep her from having a family. At age 50, she adopted daughter Dexter, now 27. Son Duke, 22, arrived five years later. “They’re great,” she says simply. “They’re doing good.” Over the past few years, though, as her nest has emptied — Dexter got married and Duke got his own place — Keaton’s golden retriever, Reggie, has become her day-to-day companion.

“A friend of mine gave her to me,” says Keaton. “I didn’t even ask for her. He came to me and said, ‘I think you need this dog.’ I was like, ‘OK, I guess?’ Of course, now I just love her. Dogs are irresistible. They’re just idiots. Reggie is a big jerk, and she’s a great jerk, and she’s hilarious.”

On Instagram, Reggie can be seen greedily soaking in Keaton’s attention while the actress, looking into the dog’s eyes, croons “How Deep Is the Ocean?” Keaton captioned the post, “Don’t forget to sing to your dogs!”

One of Keaton’s main inanimate passions is photography. Her time in Italy during last year’s shoot for the Book Club sequel “was one of the best experiences ever for me on a movie,” she says. “My entire trip was really about all of the things I saw and took pictures of. You walk around the streets and don’t know what you’re going to come across — that’s how rich it is.” On Instagram, Keaton posted a montage of door and window photos she’d snapped in Italy, calling doors “my new obsession.” Her friend Allison Kaye, a manager, commented: “Obsessed with you.” Replied Keaton: “❤️❤️❤️”

Diane Keaton’s boots in front of a framed photograph by Ruven Afanador.

Photo by: RUVEN AFANADOR

The actress has published three memoirs in all: Then Again, a remembrance of her mother, in 2011; Let’s Just Say It Wasn’t Pretty, on the culture of beauty and Keaton’s iconic style, in 2014; and the intimate and heartbreaking Brother & Sister, the story of her brother, Randy, and his battle with mental illness and alcoholism, in 2020.

“He passed relatively recently — it’s been a couple of years,” Keaton says, with a catch in her voice. A poet and artist, Randy “had a hard time with the world at large and just in life,” she says. “He was so delicate in some ways, so sensitive. He was a real artist at heart.”

After Randy’s death, Keaton shared some of his collages with her followers in an Instagram video. “I love this one,” she says of a bold, abstract work in tones of red, cream and blue. “What is it about? I’ll never know. I’ll never understand.”

Keaton has a small team that helps her put together her Instagram videos and posts. “I need the help, and I cherish it,” she says. “It’s like making little movies, in a way. It’s collaborative.”

Not too long ago, she posted a video that one of her helpers had shot of Keaton doing a goofy dance outdoors to the Miley Cyrus song “Flowers.” “Your incredible song gave me a reason to dance in my own backyard!” Keaton wrote, tagging Cyrus. The post received nearly 1 million likes, including from admirers Lindsay Lohan, Ellen Pompeo, Alicia Keys, Kerry Washington and Roma Downey.

“It was just one of those days when I thought, I’m going to do something stupid,” she says of the viral post. “The music was on, I was outdoors and thought, What the heck. It happened out of nothing.”

Maybe that’s the answer to my earlier question: What is Diane Keaton’s eccentric appeal, the reason she has stayed for so many years on Americans’ screens and in their hearts? It could just be that she lives life on her own idiosyncratic terms — and encourages the rest of us to try it too.