Luke Bryan admitted it was “very intimidating” to share the stage with Chris Stapleton.

Bryan recently hosted his sold-out “Luke & Friends” concert at Bridgestone Arena in Nashville, Tennessee, celebrating the release of his ninth studio record, Signs. The five-time Entertainer of the Year invited a star-studded list of surprise guests throughout the show, including Stapleton, Dierks Bentley, Kane Brown, Darius Rucker, Jason Aldean, and Carrie Underwood.

“The first night I never had any fans want a refund,” Bryan joked during an appearance on The Tonight Show Starring Jimmy Fallon on Sunday (September 27), after listing the friends who performed at the show.

Bryan told Jimmy Fallon that some fans might not realize, “Chris Stapleton actually wrote one of my songs, ‘Drink a Beer,’ that was one of really — historically, one of my most emotional songs.” Stapleton co-wrote the ballad with Jim Beavers. It appeared on Bryan’s Crash My Party in 2013. “And this was before Chris became Chris, and he actually performed it with me at the CMA Awards, and he is the background singer on the actual record,” Bryan explained. “So, he and I finally got to really do a real [duet, which was an] intimate moment.

“The interesting thing that I didn’t know about Stapleton is when — he’s such an amazing singer. I have him as my No. 1 on Mount Rushmore, by the way. He’s my favorite singer,” Bryan continued during his appearance on The Tonight Show. “Well, then I’m staring at [Stapleton], and he really stares at you, like, while he’s singing at you. Because he’s watching your lips. And then as he’s watching your lips, it’s very intimidating, and then the whole time I’m kind of falling in love. …He’s looking at you, and he’s got — you know, he’s a Kentucky guy, bluegrass guy, man. They watch you sing.”

Bryan went on to perform the title track of his new album on The Tonight Show. The 12-track project also includes “Country And She Knows It,” “Made It A Memory,” “I Liked Loving You,” “Finders Keepers” with Luke Combs, and more. Signs follows Bryan’s Mind Of A Country Boy (2024), Born Here Live Here Die Here Deluxe (2021), Born Here Life Here Die Here (2020), What Makes You Country (2017), Kill The Lights (2015), Crash My Party (2013), Tailgates & Tanlines (2011), Doin’ My Thing (2009) and I’ll Stay Me (2007).

“This record is a little bit of everything that shaped me,” Bryan said in the Signs album trailer earlier this year. “It’s heartbreak and healing, backroads and barstools. It’s the signs you miss and the ones you can’t ignore. It’s the nights that went wrong and the ones you wish you could live again. It’s where I come from, the woods, the fields, the people, and how love, loss, and time have a way of straightening you out or crooking your rows of corn for good. These are my signs.”

Watch Bryan’s interview on The Tonight Show here, and watch his performance below.