Long before Luke Grimes joined the Yellowstone cast and went to Montana to play Kayce Dutton, he was living in LA. Back when he first moved to California, he had quite the run-in with two iconic women, too. Now, he’s sharing the story from 20 years ago about the time he tried to hit on Drew Barrymore and Cameron Diaz.
Now, as Grimes was promoting the release of his Yellowstone spinoff, Marshals, on the 2026 TV schedule, he dropped by The Drew Barrymore Show. When he walked onto the stage, the host seemed very excited to meet him. However, he quickly set the record straight, with the following conversation:
- Luke Grimes: You want to hear something crazy?
- Drew Barrymore: What?
- Luke Grimes: We've met before.
- Drew Barrymore: How, because I’ve…Where?
Well, he sure told her where. According to Grimes, they met at a club because he was dared by a friend to go up to her and Diaz, who have famously stayed friends since making Charlie’s Angels. In the Marshals star’s words:
This story's gonna make me sound terrible. This was like 20 years ago. In LA. I had just moved to LA, and do you remember that club Teddy's?
In response to that question, Barrymore said “of course,” which prompted Grimes to continue his story. Recalling why he ended up walking up to her and Cameron Diaz while there all those years ago, the Yellowstone star said:
And you were there with Cameron Diaz, and a friend of mine was daring me to go up to women and say pick-up lines, and he dared me to come up to you two and do it.
Barrymore, who was enamoured by this story, asked Grimes what happened after that. He explained that he did work up the courage to talk to the Charlie’s Angels stars. He also recalled the two actresses’ reactions to his pick-up line, explaining:
I forget what line it was, but I did, and Cameron hated it. And you were like, 'That's actually pretty cute.' And you were nice about it, so thank you. You didn't totally reject me. Thank you for being nice to me.
Barrymore quipped amid this that Diaz’s reaction felt on-brand. Meanwhile, she affirmed her own reaction too, telling Grimes, “Thank you for even trying to fake a pickup line.” So, clearly, she was charmed by this whole ordeal then and now.
All this reminded me of how much I’d love to see Barrymore and Diaz make a movie together. However, now I’m thinking a good co-star for them could be Luke Grimes. Maybe his game can be better in a movie than it was in that club two decades ago.
Now, I’d really be curious to hear what Cameron Diaz thinks of this story, especially now that Grimes isn’t an unknown actor. He’s a vital part of the Dutton family tree, a big CBS star, and you can stream his show (which airs live on CBS every Sunday at 8 p.m.) with a Paramount+ subscription.
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