Halfway through his 50-minute set, Jelly Roll was joined by T-Pain for their cover of Toby Keith‘s hit song "Should've Been a ...

Jelly Roll took a break from touring to visit Toby Keith's OK Kids Korral, which houses families of child cancer patients.

Toby Keith is more than just a country superstar ... Starting with his 1993 debut single, 'Should've Been a Cowboy,' Keith has scored an enormous string of 19 No. 1 hits. He's most closely ...

Toby Keith, a major country music star who sold ... Keith rose to fame in the 1990s with songs such as Should've Been a Cowboy which topped the country music chart. He announced in June 2022 ...

“One of the most successful country artists of his generation, Toby Keith balanced his innate brashness and bravado with a sly wit, a talent for catchy melodies, and a cowboy poet’s flair for ...

Jelly Roll made his debut performance at Stagecoach Friday night and brought T-Pain on stage to pay tribute to Toby Keith. The duo took on the classic country hit “Should've Been a Cowboy” for ...

Oklahoma native Toby Keith Covel got his first guitar as ... and its first single, "Should've Been a Cowboy," became his first No. 1. Since then, Keith's ridden a consistent streak of Top 10 ...