WATCH: Chris Stapleton Performs ‘You Should Probably Leave’ with Jimmy Fallon on Guitar

When Chris Stapleton‘s longtime producer and collaborator, Dave Cobb, had to bow out of his performance alongside the superstar on…


Lauren Jo Black

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October 6, 2021

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Jimmy Fallon, Chris Stapleton; Photo by Sean Gallagher, NBC

When Chris Stapleton‘s longtime producer and collaborator, Dave Cobb, had to bow out of his performance alongside the superstar on The Tonight Show on Tuesday evening, Jimmy Fallon was quick to step in. 

“I got a text last night from Chris saying that his guitarist, Dave Cobb, has an earache and so he could not travel. He couldn’t fly on a plane. He’s fine, he just couldn’t fly,” Fallon revealed. “He said, ‘I need a guitarist’ and I said to Chris, ‘say no more.’”

Before Stapleton arrived in New York for his performance, the pair hopped on a FaceTime call to practice.  

“You tried to teach me the lick and the chords of the song and I’m going to try my best,” laughed Fallon as he made his way to the stage to join Stapleton and his wife, Morgane for the performance. 

The Tonight Show host held his own alongside the current five-time CMA Awards nominee for a performance of “You Should Probably Leave.” Click below to watch.

“You Should Probably Leave” is featured on Stapleton’s latest album, Starting Over

Stapleton leads the pack of CMA nominees with nods in five categories: Entertainer of the Year, Male Vocalist of the Year, Album of the Year (Starting Over), Single of the Year (“Starting Over”) and Song of the Year (“Starting Over”). He also earned additional producer credits in both the Album of the Year and Single of the Year categories. 

The five-time GRAMMY winner is in the midst of his All-American Road Show tour. Upcoming stops on the run include New York’s Madison Square Garden, two nights at Nashville’s Bridgestone Arena and Washington State’s Gorge Amphitheatre. 

Next spring, Stapleton will headline “A Concert for Kentucky”—a special performance to be held at University of Kentucky’s Kroger Field on April 23, 2022. The concert is the first ever held at UK’s Kroger Field and will feature very special guests Willie Nelson and Family, Sheryl Crow and Yola. 100% of the concert’s net proceeds will benefit Stapleton’s newly created Outlaw State of Kind Hometown Fund.

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Lauren Jo Black

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Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for and her work being featured on She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.