Lady Antebellum, Jason Isbell Serenade Kris Kristofferson on 'Skyville Live'

Brandy Clark and Raul Malo were also on the bill for the innovative online concert, broadcast live from Nashville

Skyville Live producers Tisha Fein and Wally Wilson are pictured with Dave Haywood, Charles Kelley, Brandy Clark, Hillary Scott, Kris Kristofferson, Kelsey Matthews, Raul Malo, Amanda Shires and Jason Isbell. Credit: Getty Images for Skyville Live

"Kris Kristofferson is the greatest songwriter alive today," declared Willie Nelson in a pre-taped introduction to Tuesday night's Skyville Live web concert. And for the next hour and a half, his friend's unparalleled talents were celebrated and complemented by fellow musicians whose own careers Kristofferson has incredibly influenced.

Lady Antebellum, Jason Isbell, Amanda Shires, Brandy Clark and surprise guest Raul Malo joined the legendary Kristofferson for Nashville's newest online concert series, which made its debut in January. Their set list was a mix of the man of the hour's classics and the accompanying artists' own hits, with Lady A joining Kristofferson to kick the night off with an aching ballad covered by everyone from Elvis Presley and Sammi Smith to Olivia Newton-John and Mariah Carey: "Help Me Make It Through the Night."

"His songwriting is unlike anybody else," Lady A's Dave Haywood told Rolling Stone Country before the show. "Our whole format is based around these songs he wrote. It's amazing how worldwide of an artist he is, what he's accomplished, how many people have covered these songs."

"It's unreal just to be around him, in his presence," added bandmate Charles Kelley. "He's constantly smiling."

After the indeed continually beaming Kristofferson's only solo performance of the night, on the woefully poignant "Sunday Morning Coming Down," Lady A returned for their own mini-concert, picking up the tempo with their hits "Run to You," "American Honey" and a new song from their 747 album, "One Great Mystery" — written "about the loves of our lives," Kelley explained.

Married duo Isbell and Shires, who is pregnant with their first child, were up next, with the Americana Association's reigning Artist of the Year admitting to the audience in his Alabama drawl, "I didn't realize [Kristofferson] would be sitting right in front of us. . . I feel like trying other things I'm not capable of." He then launched into "The Pilgrim, Chapter 33" with his wife on violin, turning Kristofferson's galloping story song about a lost soul into an aching power ballad and prompting Kristofferson to jump out of his front-row seat, with the entire audience following in a standing ovation.

Fans were out of their chairs again after Isbell belted his seductive "Cover Me Up," which he wrote for Shires before they were wed. They followed with a duet on Warren Zevon's "The Mutineer" and Isbell's "Live Oak," a haunting tune about a hardened criminal who falls in love, only to resort to his murderous ways with the object of his affection.

"I was watching Jason Isbell rehearse, and that's an artist incredibly influenced by Kris Kristofferson," says Kelley. "We all are, as songwriters. But those two cats, Jason specifically, I was like, 'Man, that's probably the closest thing I've heard to Kristofferson-esque lyrics that dig deeper than anything I could ever go to."

Songwriter extraordinaire Brandy Clark followed Isbell with angelic vocals on Kristofferson's "Please Don't Tell Me How the Story Ends," followed by the devilishly delicious "Crazy Women," off her Grammy-nominated 12 Stories album.

"I've always wanted to write songs like him," Clark tells Rolling Stone Country of Kristofferson. "He's also a Rhodes Scholar, a helicopter pilot, an actor. It shows me that you can always add another chapter to your book."

The Mavericks lead singer Raul Malo ("probably the best vocalist of our time," gushed Kelley) followed Clark with a jaw-dropping rendition of "For the Good Times" — another standing-ovation prompter. And the show wrapped with a Lady A sing-along, first on their gigantic crossover hit, "Need You Now" — which you might call the modern-day "Help Me Make It Through the Night," released some 40 years after. The trio were then joined by Kristofferson and budding Skyville artist Kelsey Matthews in taking the audience to church on the rousing "Why Me." To cap it all off, three famous fans in the audience were called up on stage — Jewel, Martina McBride and JoDee Messina — to harmonize with all of the evening's performers on Kristofferson's beloved "Me and Bobby McGee."

Skyville Live is an innovative webcast that is broadcast live in front of an audience of less than 200 inside its namesake Nashville studio, but with a limitless web audience. Its inaugural episode featured McBride, Gladys Knight and Estelle.

"Fans really love it, because you're bringing it to them. They can just be in their living room, and it's different from an awards show because it's like a little concert, a really intimate performance," says Clark.

"I love that this is in Nashville and is all about songwriters," adds Haywood. "It feels inviting and loose, and it's really a fun environment."