Kendall Jenner & Chris Stapleton Talk Whiskey, Tequila, & The Power of Sad Songs

This might be one of the most unexpected pairings we’ve seen in a while: Kendall Jenner and Chris Stapleton sitting down for a drink. And not just a drink, multiple drinks, made with both of their liquor brands, 818 Tequila and Traveller Whiskey.

It sounds like a strange combination, but somehow, it works.

The two came together for a promo video highlighting their respective spirits. But instead of a dry product plug, the video ends up offering something way more interesting: a glimpse into Stapleton’s mind and a surprisingly natural dynamic between the two.

Jenner, who says she’s a longtime fan of Chris, recalls flying out to Nashville with her friends just to see him perform. Apparently, she danced so hard her boots gave out. Both heels snapped off. At some point that night, Stapleton signed the bottom of her shoe, which Jenner jokes about:

“You signed the bottom of my shoe and it sits on my shelf. Just so you know, if that’s not creepy”

He just laughs and agrees.

“Maybe a little.”

They start mixing drinks, beginning with a classic Old Fashioned, which Chris casually admits he’s never had before. Kind of shocking, considering the man built a whiskey brand and looks like he’s been drinking bourbon since birth. His verdict? Not strong enough. So he follows it up with a straight pour of Traveller.

Next, they try a tequila-based Old Fashioned, and surprisingly, Stapleton likes it even more. As far as drink pairings go, whiskey and tequila might not be the most obvious duo, but in this case, they’re not fighting each other.

Then the tone shifts.

Chris’s wife, Morgane, asks Kendall a simple question:

“Do you like sad songs?”

She says yes. One of the crew laughs and calls her a “sad person,” but then Stapleton drops a line that completely reframes the moment:

“Do you know why I think we love sad songs? Because it makes us not feel alone in sadness.”

Simple. Honest. Spot on. And totally in line with why Stapleton’s music hits the way it does.

The video wraps with Jenner playfully suggesting he should write a song about her and 818. Everyone laughs, and that’s that.

Even with all the unexpected pairings: tequila and whiskey, LA and Nashville, it never feels forced. Just two people talking about music, drinks, and why sad songs matter. And sometimes, that’s all you need.

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