How Diane Keaton outwitted ageism and bad reviews to still reign supreme in Hollywood at 77

With an unmistakable style and a freedom unheard of in the industry — she is one of the few stars who support Woody Allen — the actress is racking up projects and is about to release a film about falling in love after retirement

Diane Keaton at a Ralph Lauren fashion show in San Marino, California, in 2022.
Diane Keaton at a Ralph Lauren fashion show in San Marino, California, in 2022.Amy Sussman (Getty Images)
Eva Güimil

Diane Keaton claims she got the role of Kay Adams in The Godfather because she was a “nutcase.” More than fifty years later she is still Hollywood’s favorite eccentric — a rarity in the industry. While other stars follow fashion, she is fashion. Ever since she appeared in Annie Hall (1977) with a bowler hat, tie and baggy pants, her style has been imitated every season by some celebrity or other. She speaks openly about her disdain for plastic surgery and her problems with bulimia. And of her relationships with stars such as Woody Allen, Warren Beatty, and Al Pacino, and her reluctance to marry: “I think I am the only woman of my generation who has not married.” She is not, but she is one of the actresses with the most entries in the prestigious American Film Institute’s best film list, although for years she has more often been seen in TV movies that are not up to her talent.

She is at an age when women are invisible to the industry, but her five projects in pre-production prove that cliché wrong. In April she released Maybe I Do alongside Susan Sarandon and Richard Gere, and this Friday sees the release of Book Club 2: The Next Chapter, the sequel of the movie she starred in four years ago with Jane Fonda, Candice Bergen and Mary Steenburgen — an unpretentious comedy that became an unexpected success (with a budget of $10 million, it grossed $90 million). “In an industry that defines ‘mature audiences’ as anyone old enough to vote, a movie focused entirely on women over 65 (a sex comedy, no less) seems like something of a minor Hollywood miracle,” said Entertainment Weekly. The second movie contains the same ingredients as the first and adds the beautiful Italian scenery and prosecco. No one could ask for more.

Or almost no one. Some people put Keaton in the same box as Robert de Niro, whose career seems more focused on making money than prestige. “What does this guy spend money on?” wondered Anjelica Huston in a jaw-dropping conversation with Vulture in which she claimed to be disappointed by the kind of movies some people she admired were willing to make. “I’m looking for movies that impress me in some way,” she said, “that aren’t apologetically humble or humiliating like ‘Band of cheerleaders gets back together for one last hurrah.’”

Keaton and Woody Allen in ‘Annie Hall.’
Keaton and Woody Allen in ‘Annie Hall.’Bettmann (Bettmann Archive)

It was not a random example. Days later (it was 2019) Keaton released Poms, whose plot was exactly that: two seventy-somethings reunite to reform their old cheerleading squad. Keaton made no acknowledgement, but another cheerleader, Jacki Weaver, was not so graceful. “Well, she can go fuck herself,” was her response. The incident provided the film with unexpected free publicity and proved that there is no age for sauciness. Keaton doesn’t seem to be too affected by the criticism. She doesn’t take herself and her talent too seriously. “I’m not Meryl Streep,” she used to tell filmmaker Zara Hayes when she directed her in Poms.

The Houston dig is a rarity. Looking at her Instagram account, which has nearly two million followers, Keaton seems to attract only compliments. No one loves her more than Woody Allen. “One talks about a personality that lights up a room, she lit up a boulevard,” he wrote in Apropos of Nothing. He calls her his North Star and she is the person he turns to when he has doubts about his material because he knows she has her own judgment.

“Woody got used to me, he couldn’t help it; he loved neurotic girls,” she wrote in her memoir Now and Forever. He chose her for her first major role, the theatrical version of Play It Again, Sam (1972). They fell in love during rehearsals. The romantic relationship did not last, but the friendship did. He directed her seven times, and the apex of her career came with Annie Hall, an undisguised homage to the actress (in fact Keaton’s real last name is Hall). Thanks to that film she won the Oscar for Best Actress in a Leading Role and defined her image. Her unmistakable style delights fashion magazines, although, for Allen, “it’s as if her personal shopper were Buñuel.” The last collaboration between the two came after the traumatic end of Allen and Mia Farrow’s relationship. Shooting on Manhattan Murder Mystery (1993) was imminent, when Allen called Keaton. The actress immediately took a plane from Los Angeles and flew to New York, despite the fact that Farrow (who had accused Allen of child abuse only days earlier) insisted on starring in the film.

Diane Keaton poses for the press in 1995 during the Muse Awards celebration in New York.
Diane Keaton poses for the press in 1995 during the Muse Awards celebration in New York. Ron Galella Ltd (Ron Galella Collection via Getty)

When the #MeToo movement reignited interest in the case that had filled front pages in the early 1990s, Keaton was among the few stars who remained loyal to Allen. Coming under pressure from social networks, actors like Timothée Chalamet, Kate Winslet and Greta Gerwig, who had worked with Allen after the accusations became known, rushed to distance themselves from the director. Keaton was sharp in her criticism. “Woody Allen is my friend and I believe in him.”

That their friendship can withstand anything is evidenced by the fact that it endured after the director dated Keaton’s her two sisters after dating her. “There are good genes in that family,” the director wrote.

Allen established her as a comic actress, but Keaton is so much more. A few weeks before the premiere of the film adaptation of Play It Again, Sam, audiences had discovered her as the long-suffering Kay Adams in The Godfather, a splendid debut that the actress still can’t explain. At the time she had a naïve, fun profile, but she went to the audition anyway at the suggestion of her agent. Coppola thought she could bring a spark to the character because she was “eccentric and weird.” She confesses that she based her performance on how isolated she felt on an all-male set. As with Allen, she fell in love with her co-star Al Pacino, with whom she had an on-again, off-again relationship. “Al was never mine. I spent twenty years losing a man I never had.”

The situation repeated itself with Warren Beatty, her director and co-star in Reds (1981), although she has said about the relationship: “I wasn’t in love with Beatty, I wanted to be Beatty.” Their breakup was influenced by the harshness of filming Beatty’s epic about John Reed and the origins of the Communist Party in the United States. Her role as Louise Bryant, a housewife who turns her back on her affluent, conventional life to work as a reporter in revolutionary Russia, is one of the most brilliant of her career. Beatty had also called her to star in the successful Heaven Can Wait (1978), but she preferred to continue to cultivate her dramatic profile in Looking for Mr. Goodbar (1977), the devastating story of an angelic teacher of deaf children who roams the slums of her town at night in search of casual sex. It was one of those films that shocked the society of its time and was a sociological phenomenon that was contemporary with Annie Hall. Suddenly, the small-town Californian who, at the age of twenty-five, was thinking of leaving the movies due to lack of self-confidence, was Hollywood’s brightest star.

Although dramas have brought her the highest praise, it is comedy where she feels most comfortable. In Baby Boom (1987) she played an executive who, after moving to a Vermont town to take care of an inherited baby. Her character discovers the true meaning of life by packing jam and falling in love with the adorable and sexy rural veterinarian played by Sam Shepard. It was her first collaboration with screenwriter and director Nancy Meyer, who also wrote the screenplay for The Father of the Bride (and its sequels) and for what is so far Keaton’s fourth Oscar nomination and the movie that brought her back to the A-list after a few years of drought, Something’s Gotta Give (2003). The film was a box-office hit that grossed over $250 million in which she plays a writer whose heart is torn between Jack Nicholson and Keanu Reeves.

Al Pacino and Diane Keaton at the premiere of ‘Sea of Love’ in New York in 1989.
Al Pacino and Diane Keaton at the premiere of ‘Sea of Love’ in New York in 1989.Ron Galella, Ltd. (Ron Galella Collection via Getty)

Rumors claimed that Keaton and Reeves had been in a relationship during filming. Neither of the two has spoken about it, but what the actress has confessed is her devotion to Jack Nicholson whose kisses caused her to forget her lines. The best was yet to come when, two years later, when she received a check full of zeros from Nicholson. The actor gave her a percentage of his salary, since she had been paid much less than him despite the fact that they both had the same leading role. The pay gap is a timeless tradition in Hollywood.

The movie’s success surprised Keaton. “No one was hiring me to play the lead in a romantic comedy. I was 55 years old.” The pre-success drought made her rethink her career, as at the time she was making more money restoring and selling houses (Madonna was one of his clients). She also writes books on architecture and design and is an excellent photographer. When they met, Warren Beatty told her she should be a director and she listened. She has shot documentaries, films, episodes of series such as Twin Peaks and directed several music videos for Belinda Carlisle. She has also starred in other artists’ videos: a couple of years ago she surprised audiences by declaring herself a devoted fan of Justin Bieber, whose grandmother she plays in Ghost.

Keaton knows she is an attractive woman, “not pretty,” in her own words. At 77, she is one of the few actresses who has not succumbed to plastic surgery and considers her gray hair and wrinkles part of her personality. “My thought on plastic surgery is this: I haven’t done it, but I never say never,” she explained to The Hollywood Reporter. “Because when you say it, you’re definitely going to go there. I said I would never have intercourse before I got married, and I did. I said I would never go to a psychiatrist, and I spent much of my life in psychoanalysis. I’ve done all kinds of things I said I wouldn’t do and, of course, now I’m glad.”

Her relationship with her body has not always been smooth. In her autobiography she revealed that she had suffered from bulimia. Her problems began while she in the musical Hair on Broadway. After the leading lady had to leave, the producer suggested that Keaton could replace her if she lost weight. She went to a doctor who gave her some weight-loss pills, but then resorted to vomiting. “After six months of getting rid of twenty thousand calories a day I became hypoglycemic. I had heartburn, indigestion, irregular periods and hypertension. The pain in my throat was torturing me,” she explained in her memoirs. She gorged herself on laxatives and her dentist found twenty-seven cavities. “But the worst were the psychological effects. I became more and more isolated. I didn’t think about friendships. I was unable to feel shame. I was too busy ignoring reality.”

She claims to have gone decades without a date. At the age of 50, she decided to take on single motherhood and adopted two children, Dexter and Duke. Since they left home, her companion has been her beloved Labrador Reggie. Her diary is still full of projects. Hyperactivity may be the secret of perennial enthusiasm. And also self-esteem. On her last birthday she posted a message on Instagram that is a self-help manual in itself, “Happy birthday to the love of my life... me!”

Keaton photographed in New York this spring.
Keaton photographed in New York this spring.Raymond Hall (GC Images)

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