At the Toby Keith: American Icon tribute held at Nashville’s Bridgestone Arena, country star Luke Bryan blended personal remembrance with his homage to Keith. The event, which featured performances by Lainey Wilson, Carrie Underwood, and others, was a heartfelt send-off for the country legend.
During his rendition of Keith’s hit “Should’ve Been a Cowboy,” Bryan paused to retrieve a significant accessory from his past—a black cowboy hat gifted by his late sister. Bryan, 48, shared with the audience that the hat had been a treasured gift when he was starting out in his career and had remained in his closet for about 15 years.
Bryan’s sister, Kelly, passed away suddenly in 2007, leaving behind her husband, Ben Lee Cheshire, and their three children. Cheshire also died in 2014, leaving the children without parents. Reflecting on the hat’s emotional significance, Bryan explained that he had not worn it on stage since his sister’s passing.
Holding up the hat, Bryan said, “I’m just an ol’ country boy from Georgia, but Toby Keith certainly made me want to be a cowboy. I am going to be a cowboy tonight. This is for you, Toby.”
The poignant moment, captured on video, resonated deeply with fans, who praised Bryan’s tribute on social media. “That’s so special—double honor your sister and Toby,” one TikTok user commented, while another added, “You know he sang right along with you from Heaven.”
