Jelly Roll honors Toby Keith with T-Pain as part of guest-filled Stagecoach set

Jelly Roll, one of country music's fastest-rising stars, squeezed multiple guests into his 50-minute set at the Stagecoach country music festival Friday night highlighted by a team-up with rapper T-Pain to honor country legend Toby Keith who passed away earlier this year.

Midway through the set, T-Pain came out to join Jelly Roll and the two sang Keith's classic "Should've Been a Cowboy" to honor the country legend that inspired them both.

"I had been covering 'Should’ve Been a Cowboy' for about a year now at most of my shows, just kind of honoring Toby as he was getting sick before he passed away," Jelly Roll told Variety. "Then I really started chewing on, man, what better place to honor Toby than Stagecoach? Plus, Toby Keith was one of the artists that from afar, even though he would never have known it, encouraged me to do country music."

Jelly Roll setlist: Everything he played at Stagecoach on Friday

It was one of several memorable moments during Jelly Roll's set right before headliner Eric Church.

He brought out country music compadre and writing partner Ernest for Jelly Roll's most popular song "Son of a Sinner." Regrettably, Ernest's mic didn't work at all, making for an awkward listening experience for the colossal crowd at Stagecoach's Mane Stage. Ernest plays his own set Saturday and hopefully will have better luck.

The very next song featured more special guests as Maddie & Tae (also playing their own set Saturday) joined Jelly Roll for what he said was a brand new song called "Liar." Thankfully Ernest didn't hand off his mic to Maddie or Tae.

He then ended the night when his favorite special guests, his wife, Bunnie XO, and daughter, Bailee Ann. Bailee turns 16 next week and he had all 70,000 fans sing "Happy Birthday" to her while she swayed and smiled and blushed.

But it was the songs without guests where Jelly Roll shone the most as he was able to hammer home his message about second chances and getting your life together. He honored the underdogs and have-nots and those who've been told they'll never amount to anything.

He wore a black coat that said "Beautifully Broken" on the back and, according to a documentary about him called "Jelly Roll: Save Me," that's what he considers himself and the people that identify most with his songs. And that's who he makes music for.

He opened with the song "The Lost," which put it beautifully "I'm better with the lost than the found."

He moved smoothly between poignant songs and straight-up party music like his rap/hip-hop medley that had the crowd singing along to "Lose Yourself" by Eminem, "Ms. Jackson" by Outkast and finally "Just a Friend" by Biz Markie.

He then finished with "Need a Favor" and "Save Me," two emotionally-charged songs. He thanked the crowd and said he had been dreaming of playing Stagecoach for years.

"But last night I had another dream," he said. "That I would be back here in a couple years as the headliner."

If Friday was any indication, with his charisma, following and variety of musical talents and talented friends, that seems like a dream that will almost certainly be achieved.

Shad Powers is a columnist for The Desert Sun. Reach him at [email protected].

This article originally appeared on Palm Springs Desert Sun: Jelly Roll honors Toby Keith with T-Pain as part of guest-filled Stagecoach set