Another great Willie Nelson story.
Today, Chris Stapleton appeared as a guest on Howard Stern’s SiriusXM’s The Howard Stern Show, where he discussed his iconic Super Bowl performance, learning to play guitar, the CMA performance with Justin Timberlake that jump-started his artist career and much more.
And of course, Stern had to ask him if he’s ever smoked with Willie, to which Chris enthusiastically responded:
“Of course! Of course. I haven’t played poker with him, that’s the other one that people do is play poker with him. But I’m a terrible poker player, so I might as well just hand him a bunch of money and just sit there and let him tell jokes. He tells great jokes.”
Like so many, Chris used to drive around in the car with his dad listening to Willie, which Stern pointed out had to have been really amazing to think about the full-circle friendship the two country stars now have.
Stapleton joked that his dad might be “a little worried” about that part…
“I think he would be worried about that part, but I think he would definitely think it was cool. I think it’s cool, to this day I see him every time I can, I play shows with him whenever I can.”
He also talked about what an honor it was to perform alongside Willie at his Rock and Roll Hall of Fame induction, where he was seated right next to his hero as Dave Matthews gave a speech and officially inducted Willie.
Chris said that he actually felt a little “weird” sitting next to him onstage, seeing as his sons were behind them and he didn’t feel like he necessarily should’ve been front and center like that. Lukas and Micah were playing in the band, so it made sense logistically, but still, I totally get his point… that feels like a really special family moment and there he was in the middle of it.
He added that he got a little choked up as he was listening to Dave talk about Willie’s career, but Willie helped in snap out of it because they had a song to perform for everyone there:
“I did the thing at the Rock and Roll Hall of Fame induction, and Dave Matthews was gonna give a speech. And Dave’s listing all of Willie’s career, and I’m sitting on stage next to Willie Nelson for his Rock and Roll Hall of Fame induction, just me.
His sons are behind us and I’m feeling kinda weird. I’m just like, your sons are behind us, man. Like, they’re in the band, also maybe they should sit up here. I didn’t feel like I should be the guy seated next to Willie, you know? Then they handed it over to Willie and I’m just really taking this moment in, very, very moving.
I was getting a little moved and choked up. And then Willie leans over to me and goes, ‘What song are we playing?’ And I go, ‘Whiskey River.’ And he said ‘Alright,’ and that just took me out of, right back to like, this is the coolest thing.”
And after seeing their performance, you’ll realize that they didn’t miss a beat, per the usual:
Chris also honored Willie with a stunning and breathtaking rendition of “Always On My Mind” at Willie’ s90th birthday party celebration lasy year, which you absolutely have to check out if you haven’t already:
And the Stern clip:





