Before the Nov. 21 concert taping, Kesha and Old Crow frontman Ketch Secor had never sung together. But they quickly bonded backstage over their mutual love for the city of Nashville, roots music and Bob Dylan.
One of the songs they perform on the concert special is the Old Crow arrangement of Dylan's "Rainy Day Women #12 & 35" and the band's signature hit "Wagon Wheel," a song Dylan started in the '70s and Secor finished 25 years later.
Kesha admitted she wept the first time she met Dylan.
"We were at the same festival, and he was really into my [Nudie] suit," Kesha told CMT Hot 20 Countdown. "He was like, 'I love your suit. You have great style.' And I just remember [thinking] I want to [take this to] my grave. It was so good."
Although the latest Old Crow album is the live Dylan tribute 50 Years of Blonde on Blonde, Secor has never met the music icon. And he would like to keep it that way.
"I kinda don't want to," Secor said of meeting Dylan.
"No, its good you should meet him," Kesha said. "They say don't meet your idols. But you [should] meet him. He's so nice."
Secor said the band was excited to work with Kesha. Rearranging her pop songs into Old Crow acoustic anthems was a fun challenge.
"We loved diving into [her] songs," Secor said. "We found that it's our folk music. Whether its pop music, country music, hillbilly music, rap or R&B, whatever it is, it's all folk music ... The formulas are the same. The spirit that moves through a song like 'Woman,' I hear it in so many soul records. And you listen to soul music, and then you listen to Dolly Parton, I mean, there's soul."
"I really like hearing ya'll sing, 'Woman,'" Kesha told Secor. "Hearing a bunch of men screaming about being a woman is really fun."
"It's really fun for me and really timely," he said. "It's a really important time of the year for a bunch of men to take on the perspective of a woman."
Hot 20's full interview with Kesha and Secor will air on Saturday and Sunday (Dec. 2-3) at 9 a.m. ET.
The hour-long CMT Crossroads will premiere on Dec. 6 at 10 p.m. ET, and it will feature new arrangements of both acts' biggest hits including selections from Kesha's latest No. 1 album Rainbow and Old Crow's expansive catalog that spans nearly two decades.