A Look Back At Toby Keith's Friendship With Blake Shelton

Nowadays, Toby Keith and Blake Shelton might hold comparable places in the country music canon but that hasn't always been the case. In the early 2000s, Shelton was an unknown artist slated to open for the late singer-songwriter while he was on tour. What started as a working relationship — with a bit of pick-up basketball added in between shows — quickly became a lifelong friendship and mutual admiration for each other's craft.

Following the news of Keith's death at 62 after an arduous fight against stomach cancer, Shelton posted a short but touching tribute to X, formerly Twitter. "Even though I knew about your battle these last few months, I still never imagined this day. Anyone who knew you knows what I mean," Shelton wrote. "You were the toughest man I ever met. Thank you brother for being a friend, a hero, and an inspiration."

The "God's Country" singer ended his tribute by saying there would never be another musician who can compare to Keith — a sentiment Shelton likely already knew back when they first started working together in 2003.

It's not uncommon for an up-and-coming musician to get their big break opening up for a larger act on a national tour, and such was the case for then-rising star Blake Shelton, who was invited to open for the late Toby Keith back in the early 2000s when his career was just taking off. According to the Shefani Archive, Shelton's first show with the "Should've Been a Cowboy" singer was at the Ford Centennial Celebration in Dearborn, Michigan, in June 2003.

The summer show would be the first of many Shelton performed with Keith, touring across the United States with him from 2003 to 2004. Shelton later told 92.5 XTU that he was playing to 15 to 20,000 people every night and while everyone in the room loved Keith, far fewer knew who Shelton was. The country star credits this slot as one of the biggest turning points in his career. And luckily, he and Keith managed to find some time to play while working. 

"We had stupid fun on the Toby tour," Shelton told the Philadelphia radio station. "There's no limit when you're on a tour like that. Nobody ever said no to anything which was new to me. We both had our own basketball teams and played basketball close to every day of the tour."

Toby Keith and Blake Shelton were both larger-than-life performers known for their no-nonsense, proudly machismo attitudes. Unsurprisingly, this resulted in more than a few friendly digs at one another over the years. Shelton described one such moment while presenting Keith with the Country Icon award at the Grand Ole Opry in 2023. The singer-songwriter explained that he was talking to Keith after another show where he was nominated for several awards but ultimately didn't win any.

"I was so excited to be able to get under his skin — I said, 'Man, Toby, if I ever make it big enough one day, and I get nominated for some awards, I hope it's against you,'" Shelton recalled. "I swear, Toby looked at me, and he said, 'You know why I brought you out on tour with me?' And I said, 'No.' And he goes, 'I wanted to prove to this industry that I don't really need an opening act'" (via E! News).

Razzing aside, it's clear that Keith and Shelton greatly respected and loved one another. At the 53rd Annual ACM Awards in 2018, the two men enthusiastically performed Keith's breakout hit, "Should've Been a Cowboy" (via YouTube). The superstars' giddy performance was a touching glimpse at the days when they lived on the road, played basketball, and won over crowds nationwide.