Diane Keaton and Woody Allen first collaborated on the latter’s 1972 play, Play It Again, Sam. They developed a relationship off-screen at the time, and a source shared with RadarOnline that the late actress never stopped loving Allen. This brief romance was allegedly the most defining relationship that Keaton had in her life.
The source shared that this romance transcended all the controversies surrounding the filmmaker and her high-profile romances with Al Pacino and Warren Beatty. They shared that Keaton described Allen as an invincible “cockroach.” The source shared:
Diane always had this deep, strange affection for Woody that never went away. Even when she was seeing Al or Warren, there was this sense that Woody had her heart. She called him her ‘cockroach,’ which was her way of saying he was indestructible – impossible to get rid of.
Allen and Keaton’s best collaboration was the 1977 film, Annie Hall, which brought them both Oscars. The source shared that Keaton credited Allen “for bringing out her best self on screen.” They added, “That film was their love story in disguise.” The actress wrote about Allen in her 2012 memoir, Then Again, sharing:
I miss Woody. He’d cringe if he knew how much I care about him, but I’m smart enough not to broach the subject. He’s borderline repulsed by the grotesque nature of my affection.
In his essay for The Free Press after Keaton’s passing, Allen recalled the first time that he met her. He shared, “When we first met, I thought she was so charming, so beautiful, so magical, that I questioned my sanity. I thought: Was it possible to fall in love so quickly?”
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. She went on to date a number of exciting men, all of them more fascinating than I was.
Besides Annie Hall, Keaton and Allen worked together in films including Sleeper, Love and Death, Interiors, Manhattan, and Manhattan Murder Mystery.
Diane Keaton Allegedly Never Committed Fully to a Relationship After Woody Allen
Diane Keaton had several other high-profile Hollywood relationships after Woody Allen. Keaton and Al Pacino met on the set of The Godfather in the ’70s and began a years-long, on-and-off relationship. She gushed about her former lover during a 2017 interview with PEOPLE. She shared:
I was mad for him. Charming, hilarious, a nonstop talker. There was an aspect of him that was like a lost orphan, like this kind of crazy idiot savant. And oh, gorgeous!
Keaton and Pacino finally split in 1990 when the latter refused to commit to marriage. It was reported that Keaton pushed for marriage and gave him an ultimatum. After Keaton’s passing, a friend of Pacino told the Daily Mail that he would forever regret not marrying Keaton.
She was also involved with another legendary actor, Warren Beatty, when she was working on 1981’s Reds with him. According to RadarOnline, friends of the actress shared that she “never gave her heart away fully” after Allen. A source told the outlet:
Woody was the one constant. No matter how successful she became, she’d always light up when someone mentioned his name.
She told PEOPLE back in 2019 that she didn’t think it was “a good idea for me to have married.” She shared that she was glad she didn’t marry any of her exes, adding that they would also be happy about that decision.
Diane Keaton Defended Woody Allen When He Was Accused of S*xual Assault
Diane Keaton publicly defended Woody Allen when he was accused of s*xual abuse toward his daughter, Dylan Farrow. Allen repeatedly denied the allegation over the years, and he was never charged with any crime. Allen’s then-wife, Mia Farrow, broke off the relationship in the ’90s after the allegations.
The issues were brought up again in the wake of the #MeToo movement. However, Keaton chose to support her ex-lover, sharing on X in 2018, “Woody Allen is my friend and I continue to believe him” (via PEOPLE). She shared a link to Allen’s 60 Minutes interview from 1992 and asked people to take a look at Allen’s side.
In 2014, she was asked to comment on the accusations against the director during an interview with The Guardian. She shared, “I have nothing to say about that. Except: I believe my friend.”
Despite her publicly defending Allen, Mia Farrow shared a tribute to the late actress on Instagram. She wrote about Keaton’s career and character in her message, sharing, “She was an absolutely wonderful actress – and a rare and fascinating person.” She added, “Thoughts with her children and sisters. Rest in peace Diane.”
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