The filmmaker, who dated Keaton in the early 1970s, recalled first spotting the actress at an audition for his and David Merrick’s play, Play It Again, Sam. However, he explained that they didn’t really get to know each other until they grabbed food together one day during rehearsals.
“That was our first moment of personal contact,” he wrote. “The upshot is that she was so charming, so beautiful, so magical, that I questioned my sanity. I thought: Could I be in love so quickly?”
The pair began dating shortly afterward, and Keaton quickly became Allen’s sounding board on whether or not his films were any good.
“About then, I showed her my first film privately and prepared her for what a mess it was, how awful, a total failure. She sat through Take the Money and Run and said the movie was very funny and very original. Her words,” he stated. “Its success proved her correct and I never doubted her judgment again. I showed her every film I made after that and grew to care only about her appraisals.”
Keaton would go on to star in eight of Allen’s films, including the 1972 film adaptation of Play It Again, Sam, 1973’s Sleeper, 1975’s Love and Death, 1977’s Annie Hall, 1978’s Interiors, 1979’s Manhattan, 1987’s Radio Days, and 1993’s Manhattan Murder Mystery. She won the Best Actress Oscar for Annie Hall, whose title character was inspired by the actress. The film also won Best Picture, and Best Director and Best Original Screenplay for Allen, the last of which he shared with Marshall Brickman.
In addition to having a good eye for films, Allen noted that Keaton had a wide range of talents outside of just "comedies and drama" and could “dance and sing with feeling,” “wrote books and did photography, made collages, decorated homes, and directed films.” He added, “Finally, she was a million laughs to be around.”
He also described Keaton’s fashion sense as “a sight to behold,” noting that she put “together clothing that defied logic but always worked," and that her style became “more elegant” in later years.
Allen explained that Keaton “taught me so much” during the years that they lived together, including about the reality of battling bulimia. “This slim actress ate like Paul Bunyan,” he wrote. “Only years later when she wrote a memoir did she describe her eating disorder, but when I was experiencing it, I could only think I’d never seen anyone eat like that outside of a documentary on whales.”
He also recalled an instance in which he was introduced to her family at Thanksgiving and joined in on their great big penny poker tournament. “I wound up the big winner, clearing about 80 cents,” Allen wrote. “I don’t think the Grammys ever wanted me back. They thought I was hustling them.”
Still, he noted, “This was Keaton’s world, her people, her background. It was amazing that this beautiful yokel went on to become an award-winning actress and sophisticated fashion icon. We had a few great personal years together and finally we both moved on, and why we parted only God and Freud might be able to figure out.”
Allen acknowledged that Keaton went on to date “more fascinating” men than him after they went their split, but that the pair always remained close. “I kidded Keaton that we’d wind up — she like Norma Desmond, me like Erich von Stroheim, once her director, now her chauffeur,” he joked. “But the world is constantly being redefined, and with Keaton’s passing it is redefined once again.”
He concluded, “A few days ago the world was a place that included Diane Keaton. Now it’s a world that does not. Hence, it’s a drearier world. Still, there are her movies. And her great laugh still echoes in my head.”
Keaton and Allen remained close friends after their breakup. The actress defended Allen amid his controversies.
"Woody Allen is my friend and I continue to believe him,” Keaton wrote on X at the time. “It might be of interest to take a look at the ’60 Minutes’ interview from 1992 and see what you think.”
