Introduction
Jelly Roll has been making Toby Keith’s classic “Should’ve Been A Cowboy” a regular part of his live shows, but during a recent performance, he took things to a whole new level with a special guest no one saw coming—rapper and singer T-Pain.
The moment unfolded during a high-energy medley of hip-hop hits, where Jelly Roll covered DJ Khaled’s anthem “All I Do Is Win” and then launched into T-Pain’s hit “Buy U A Drank.” To everyone’s surprise and excitement, T-Pain himself walked on stage and joined the performance, turning the event into something unforgettable.
But the real magic happened when T-Pain stayed on stage to help Jelly Roll pay tribute to the late country legend, Toby Keith. As the opening notes of “Should’ve Been A Cowboy” rang out, Jelly Roll shouted to the crowd, “We love you, Toby!”—a heartfelt moment that clearly came from a place of deep admiration.
Watch their powerful performance of “Should’ve Been A Cowboy” below:
This special version of “Should’ve Been A Cowboy” is part of an exclusive Amazon Music Originals release by Jelly Roll. The release includes both a polished studio track and the electric live festival performance with T-Pain. Most importantly, all proceeds are being donated to The Toby Keith Foundation, which provides housing and support for families with children undergoing cancer treatment—a cause close to Toby’s heart.
The collaboration between Jelly Roll and T-Pain caught many by surprise but was widely embraced by fans and critics alike. The blending of country and hip-hop, delivered with sincerity and respect, created a moment that transcended genre boundaries.
Fans were quick to share their emotions and reactions:
- “This is what we all needed but never knew it until now.”
- “Omg love this, they knocked it out of the park… You made Toby proud.”
- “I believe T-Pain when he says ‘I Should’ve Been A Cowboy.’”
- “Love it… I need a real cover from them now…”
This wasn’t T-Pain’s first venture into country music either. In 2023, he released a stunning cover of “Tennessee Whiskey” as part of his album On Top of The Covers. Known for his signature autotune sound, T-Pain surprised many listeners with his raw, unfiltered vocals—proving just how versatile and talented he truly is.
In a night full of surprises, heartfelt tributes, and genre-crossing moments, Jelly Roll and T-Pain delivered more than just a performance—they created a moment that honored Toby Keith in a way few expected but everyone appreciated.