Jelly Roll Joined By T-Pain For “Should’ve Been A Cowboy” Tribute To Toby Keith During Stagecoach Set

Jelly Roll T-Pain

Everybody loves Toby Keith.

Since the country legend passed away on February 5th, the tributes just keep pouring in, not just from those in the country music world but from athletes, talk show hosts, the military…and even rappers.

Jelly Roll has made Toby’s signature hit, “Should’ve Been A Cowboy,” a staple of his live shows. And last night during his performance on the Mane Stage at Stagecoach Festival in Indio, California, he once again broke out the classic hit for the crowd of 80,000. But he was joined by a surprising guest to pay tribute to the country legend.

T-Pain appeared on stage as Jelly was performing a rap medley that included “All I Do Is Win,” the DJ Khaled track that features T-Pain. And he stuck around to honor the Big Dog Daddy, joining Jelly Roll for the tribute and even taking a verse for himself:

@laurennnhoward Day 1 Stagecoach 2024 🇺🇸❤️ #stagecoach #palmsprings #countrymusic #america #fy #fyp #tpain #jellyroll ♬ original sound – Lauren Howard

Of course T-Pain has dabbled in country music himself, releasing a cover of “Tennessee Whiskey” on his 2023 album On Top of The Covers. And he kind of crushed it, because although the rapper is best known for his extensive use of autotune on his music, he actually has an incredible voice.

He’s also said that he’s written popular country songs for other artists, but doesn’t put his name on the credits due to the racist backlash that he thinks he would receive:

“I’ve wrote a lot of country songs, stopped taking credit for it because as cool as it is to see your name in the credits and sh*t like that, the racism that comes after it is just…

I’ll just take the check. Don’t put me on that sh*t. I’ll just take the check, bro. Never mind dude, you know what I mean?”

I mean, after seeing what T-Pain can do, I wouldn’t be mad to hear more country music from the rapper.

A beer bottle on a dock



A beer bottle on a dock