Appreciation: Diane Keaton showed us how to dress up our insecurities and be kooky with confidence

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When Diane Keaton was eleven years old, her father suggested she’d eventually find happiness with a boyfriend. This upset her greatly. She didn’t want to be loved by just *one* boy – Diane, then known as Diane Hall, wanted everyone to adore her. This desire to be universally loved was an early indication that she was destined to become an actress.

Keaton explained in her 2011 memoir, “Then Again,” that true intimacy meant having a deep connection with just one person, not a large group. She compared it to habits like drinking and smoking, suggesting it should be approached carefully.

Diane Keaton once playfully said she preferred admiring men to dating them, explaining that she enjoyed connections with artists as long as they were mutually inspiring, and then happily remained friends. She described herself as ‘collecting men,’ and even had a wall of photos in her home dedicated to those she admired – including figures like Morgan Freeman, Abraham Lincoln, Gary Cooper, and John Wayne. When she expressed a desire to add Ryan Gosling and Channing Tatum to her collection, I jokingly suggested a film where she could ‘date’ them both. Keaton quickly shut down the idea, insisting she wanted to focus on her career and wasn’t interested in a romantic comedy just for that purpose.

Diane Keaton charmed audiences for over half a century, just as she intended. From acclaimed dramatic roles to lighthearted comedies, she captivated us with her presence. Many of her later films, like 2022’s “Mack & Rita,” simply celebrated the pleasure of watching Diane Keaton be herself.

Entertainment & Arts

Oscar-winning actress Diane Keaton, famous for her roles in movies like ‘Annie Hall’ and ‘The Godfather,’ has passed away at the age of 79.

Towards the end of her career, in films like “Summer Camp” and the “Book Club” movies, Diane Keaton often seemed to be playing versions of herself, which was always enjoyable to watch. I even noted in a review of “Mack & Rita” that when her character finally started dressing like Diane Keaton – putting on a quirky blazer and wide belt – it felt as exciting as seeing Batman don his mask.

I wanted to be Diane Keaton, even if she wanted to be Warren Beatty.

It’s ironic that the qualities fans adored about Diane Keaton – her easy humor, humble personality, and distinctive style – were actually ways she hid her own self-doubt. Despite achieving fame, Keaton constantly battled insecurity, questioning her appearance, talent, and accomplishments. She often expressed these feelings of inadequacy in interviews, speaking with her characteristic pauses and hesitant speech. In fact, she rarely gave interviews at all, especially early in her career. This made her something of a reclusive celebrity – a mysterious figure glimpsed occasionally, like a modern-day Bigfoot, wandering through Central Park to her apartment.

Journalists often compared Diane Keaton to the elusive Greta Garbo, noting her intense desire for privacy. In 1977, Time Magazine observed she ‘clutched privacy about her like a shawl,’ the same year films like “Annie Hall” and “Looking for Mr. Goodbar” proved she could play both quirky and complex characters. I particularly like that comparison to Garbo because Keaton herself described her clothing as a way to hide, an ‘impenetrable fortress.’ The more unusual and layered her outfits—like wearing jackets, skirts, pants, and boots all at once—the more she could blend into the background.

People who embrace their individuality, like me, really appreciated everything about her, especially how honest and down-to-earth she was. She taught us how to confidently navigate life, even when we were feeling anxious and unsure.

Entertainment & Arts

Diane Keaton, who died Saturday at 79, is one of cinema’s most legendary actors.

Keaton knew she wanted to be a performer, so she tried out for everything she could – the choir, cheerleading, even the school play. But she always lost the main roles to the conventionally pretty girls – it was Orange County, after all. She’d often go home and feel discouraged when she looked in the mirror. She longed to look like the bright and bubbly Doris Day, but instead saw a resemblance to the adventurous Amelia Earhart. Ironically, she would later be nominated for a Golden Globe for portraying Earhart on TV in 1994.

Keaton playfully used a clothespin on her nose, trying to minimize its size, and then fully embraced a lively, outgoing persona – complete with loud laughter and dramatic hairstyles, which she sometimes accentuated with large hats. By the time she was fifteen, she’d already begun to develop her signature style of bold black and white clothing, and she loved it so much that she even wrote a letter to Judy Garland questioning why Dorothy needed to leave the simple world of Kansas for the colorful, over-the-top land of Oz. It’s likely she was the only fan who ever thought to ask that!

Shortly after that, Keaton traveled to New York City, and a series of exciting events quickly followed. The renowned acting coach Sanford Meisner approved of her work. She landed the lead role in the popular Broadway show “Hair,” with the unique condition that she didn’t have to perform nude. Most importantly, “The Godfather,” the biggest movie of 1972, gave Keaton – a relatively unknown stage actress – a crucial close-up shot that launched her film career.

Diane Keaton earned just $6,000 for her role in “The Godfather,” which was significantly less than the $24,000 she’d made from a deodorant commercial the previous year. She didn’t talk much about her experience filming the movie, describing her wig as heavy and her part as insignificant. She recalled only one interaction with Marlon Brando, during which he made an inappropriate comment about her appearance.

Diane Keaton’s character, Kay, makes a wonderful first impression when she meets the Corleone family at a wedding – she’s warm, confident, and gently pushes her boyfriend, Michael, to explain the family’s connection to singer Johnny Fontane. It’s painful, yet captivating, to watch her character become increasingly withdrawn and hardened throughout the film. However, Keaton herself admits she’s never been able to watch the completed movie, writing in her memoir that she couldn’t bear to see herself on screen.

Woody Allen truly captured the essence of Diane Keaton in “Annie Hall,” a film clearly inspired by their relationship. He wanted audiences to see and love her unique and quirky personality, and it was incredibly successful. It remains my favorite film from both of them, a fact I readily admit. Even knowing now that the ‘Annie Hall’ I admired was a naturally reserved person playing a role, the confident and charming persona she presented on screen still feels incredibly genuine and endearing – she’s an icon who feels like a close friend.

Entertainment & Arts

Diane Keaton was deeply loved by those who worked with her, and admired by many famous faces in Hollywood. Since her passing, heartfelt messages of remembrance have been flooding in.

I also suspect Allen created “Annie Hall” hoping Diane Keaton would see herself as he did—as sexy, funny, and charming—and perhaps fall in love with that version of herself. However, Keaton only saw the film once, in a regular theater after its release, and found watching herself on screen deeply unpleasant. She didn’t even fully appreciate winning the Best Actress Oscar. As she put it, she felt she’d won for playing a slightly nicer version of herself and didn’t believe she deserved the award.

Diane Keaton’s character in the film seems confused when Alvy Singer gives her a complex book about death and philosophy. Interestingly, ten years later, Keaton herself directed a documentary called “Heaven,” exploring the same topic. The film featured interviews with a diverse group of people – from street preachers and Don King to her own 94-year-old grandmother, Grammy Hall – about their beliefs regarding life after death, just like in Allen’s movie.

The experimental film “Heaven” relies heavily on striking visuals – dramatic shadows and dreamlike clips from old movies – and feels more suited for an art installation than a traditional cinema. Pre-release screenings predicted its lack of mainstream appeal, suggesting it would only resonate with a niche audience who share the director’s unique sensibilities. Though Diane Keaton doesn’t appear in the film, her personal touch is evident in every shot, and you can feel her fondness for the way her interviewees express themselves, often hesitantly. The first person she interviews stumbles over their words, saying, “Uh, heaven, heaven is, uh, um, let me see,” a response that perfectly captures the charmingly awkward way Annie Hall might have spoken.

I really wish Keaton had felt comfortable showing her face on camera. It would have been lovely to see her talk about where she’s at in life, even if she was a bit embarrassed. She was certainly willing to be honest in her four books, openly discussing her self-doubt, her struggle with bulimia, and, as Alvy pointed out, her thoughts on mortality.

In her 2014 memoir, “Let’s Just Say It Wasn’t Pretty,” Keaton admitted to feeling fearful about the future. She questioned whether she had the strength to confront life’s uncertainties, wondering if she could take risks, embrace failure, avoid settling for less, and overcome her own tendency towards cowardice.

At last, a sliver of confidence peeks out. “But I hope so.”

On behalf of her millions of fans, I hope so too.

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2025-10-13 22:02