Diane Keaton on Jimmy Kimmel: Why Her Chaotic Interviews Are Still The Best Thing on TV

You know those rare moments when a celebrity interview feels less like a PR script and more like a fever dream? That’s basically every single time Diane Keaton on Jimmy Kimmel happens. It’s not just a chat. It’s an event. Honestly, if you’ve watched her over the years, you know Diane doesn't do "normal" talk show segments. She brings wine. She brings hats. She brings a level of chaotic energy that makes Jimmy look like he’s forgotten how to host his own show.

Looking back at her appearances, especially the 2018 and 2019 visits that went viral for all the right—and weird—reasons, there is a specific brand of Keaton magic. It’s the kind of TV where you’re simultaneously laughing and wondering if the legal department is sweating in the wings.

The Smooch Heard ‘Round the Internet

We have to talk about the kissing. Because, wow. In May 2018, while promoting Book Club, Diane decided that simply talking about her co-star Andy Garcia wasn't enough. She told Jimmy, "I like him better than you," which is a classic Diane move—brutally honest but somehow charming. Then, she forced Jimmy out of his seat to recreate a scene.

Jimmy, being the professional, asked for his "motivation." Diane’s response? "Nothing, you’re just the man."

She then proceeded to plant a massive, lingering kiss on him. But here’s the kicker: she wasn't impressed. After the segment, she looked at him and basically called him a "stiff" kisser compared to Andy Garcia. It was peak entertainment because it felt so unscripted. Most stars are so worried about their "image" that they wouldn't dream of making a late-night host look that uncomfortable. Diane? She lives for it.

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Why the 2019 "New Way of Kissing" Segment Mattered

A year later, she was back for Poms, and she hadn't let the kissing thing go. She actually complained to Jimmy that in the entire year since she last saw him, no "male person" had kissed her. She literally asked him, "You're a male, right?"

She then demonstrated a "new approach" to kissing that she hoped would end her dry spell. It involved a lot of face-touching and Diane admiring Jimmy's "soft skin" in his beard. It sounds weird on paper, but on screen, it’s just Diane being the singular, eccentric icon she is. She’s 70-something, she’s never been married, and she’s out here making one of the biggest names in late-night blush like a teenager.

The Wine, The Hats, and The "Sleazy" Studio

One of my favorite moments from Diane Keaton on Jimmy Kimmel wasn't even a specific joke. It was the 2017 interview where she just started drinking wine on set. When she expressed concern about getting in trouble for drinking on TV, Jimmy told her, "It’s a sleazy place, you learned that when you walked in."

They ended up playing a game of "Beer Pong" (or "Wine Pong," in her case). She didn't really follow the rules. She just threw the balls at Jimmy’s head. It’s that refusal to play the Hollywood game that makes her segments rank so high in the "Discover" feed years later. People crave authenticity, even if that authenticity is a woman in a giant hat drinking Chablis and refusing to name her famous friends.

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Fact-Checking the "Feuds"

There’s often talk about Diane being "difficult," but if you watch the Kimmel tapes, it’s clearly a bit. She plays a character—a heightened version of the "Annie Hall" persona we all fell in love with decades ago.

• The Andy Garcia Comparison: She frequently puts down Jimmy to praise Andy, but it’s all in good fun.
• The Fashion: Her outfits on the show—always featuring gloves, belts, and those architectural hats—are a talking point in themselves.
• The Single Life: She’s very open about being single, famously telling Jimmy she’s likely the only one in her generation who has stayed single her whole life.

Why We Still Care in 2026

Even as we look back on these moments, the appeal of Diane Keaton on Jimmy Kimmel remains the same: she is unpredictable. In an era where every late-night clip is a pre-planned "bit" designed to go viral, Diane is actually dangerous. You don't know if she’s going to kiss the host, insult the audience, or start a game of cards.

She represents a bridge to an older Hollywood where stars had real personalities. When she talks about her mother, Dorothy Hall, or her early days in The Godfather, she does it with a mix of reverence and "who cares?" that is refreshing.

If you’re looking to capture some of that Keaton energy in your own life, the takeaway isn't necessarily to go around kissing people at work. It's about owning your space. Whether she's talking about her kids, Dexter and Duke, or her "man-type" kissing strategy, she is 100% herself.

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How to Watch the Best Moments

If you want to dive down the rabbit hole, you should start with these three specific clips usually found on the Jimmy Kimmel Live YouTube channel:

1. "Diane Keaton Kisses Jimmy" (May 2018): This is the definitive one.
2. "Beer Pong with Diane Keaton": Pure, unadulterated chaos.
3. "Diane Keaton Has a Hard Time Coming to Kimmel": Where she explains her social anxiety in the most hilarious way possible.

To truly appreciate these segments, watch the body language. Notice how Jimmy leans back, giving her the floor, because he knows he can't control her. That’s the secret to a great interview. It’s a power struggle where the audience always wins.

Next Steps for Fans:
To get the full Diane Keaton experience, go beyond the talk show clips and watch her 2021 appearance in Justin Bieber’s "Ghost" music video. It captures that same "alive" energy Sarah Paulson famously praised her for. You can also track her recent fashion evolution on her official Instagram, where she continues to prove that style has no expiration date.