Chris Stapleton Talks Booze With Kendall Jenner

August 5, 2025 5:45 am Published by Cheryl Johnstone

This was not a duo I saw coming.

Kendall Jenner and Chris Stapleton had drinks recently to highlight their own brands, 818 Tequila and Traveller Whiskey.

They mixed cocktails, swapped stories, and kept it surprisingly real.

Kendall revealed she’s a longtime fan and still keeps an autograph she once got from Chris.

“You signed the bottom of my shoe, and it sits on my shelf. If that’s not creepy.”

Chris laughed and said,

“Maybe a little.” They even got a little deep at the end.

Stapleton then explained why we love sad songs so much.

When Kendall admitted she loves sad songs, Chris said,

“You know why we love sad songs? Because it makes us feel less alone in sadness.”

This post was written by Cheryl Johnstone