Watch Jimmy Fallon Join Chris Stapleton On 'The Tonight Show' Stage

By Kelly Fisher

October 6, 2021

Photo: Getty Images

Chris Stapleton performed one of his most popular songs on The Tonight Show Starring Jimmy Fallon — and he had a little help from the host himself.

Host Jimmy Fallon introduced the country singer-songwriter on his show on Tuesday (October 5). The actor and comedian explained to the audience why there there would be an “interesting performance” that night:

“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 the plane. He’s fine, he just couldn’t fly. He said… ‘I need a guitarist.’ And I said to Chris, ’say no more.’

That’s when Fallon pulled a guitar from behind his desk on The Tonight Show set, and the audience responded with cheers and applause. Fallon continued:

“We actually got on the phone and FaceTimed last (night), and you tried to teach me the lick and the chords of the song, and I’m gonna try my best, so here’s me and Chris Stapleton doing ‘You Should Probably Leave.’ I appreciate this.”

Stapleton delivered a rendition of “You Should Probably Leave,” a track from his album Starting Over, which released last year. Watch Stapleton (and Fallon) perform on The Tonight Show stage here:

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.