The country music world lost a giant on Feb. 5, 2024. Toby Keith died at age 62 following a two-year battle with stomach cancer. But the “Big Dog Daddy” left behind an indescribable legacy, scoring 20 No. 1 hits and selling more than 40 million albums throughout his three-decade career. A performer at heart, Keith’s live shows were also something to behold. Therefore, it comes as no surprise that the “Should’ve Been a Cowboy” crooner was one of just three country artists to secure his spot on Pollstar’s 25 Most Popular Touring Artists of the Millennium.
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Based on worldwide ticket sales reported to Pollstar from 2001 through the end of 2025, Toby Keith came in at No. 23, with more than 9.5 million tickets sold and grossing over $400 million total.
According to Pollstar, the “Red Solo Cup” singer’s highest-grossing show came at Gillette Stadium in Foxborough, Massachusetts on July 24, 2004, the opening night of his Big Throwdown Tour. Supporting acts included Jo Dee Messina, Montgomery Gentry, Gretchen Wilson and Scotty Emerick. The show racked up $2.9 million in ticket sales, equivalent to about $4.7 million in today’s dollars.
Kenny Chesney, Luke Bryan Join Toby Keith on Top Touring Acts
Toby Keith was just one of three country stars to make Pollstar’s list. Kenny Chesney is the highest-ranked country headliner, coming in at No. 7 with $18.2 million in ticket sales. In an official statement, the “No Shoes, No Shirt, No Problems” star expressed his shock at the news.
“I only really think about all those faces smiling, laughing, singing—it’s the most beautiful sea of love and joy imaginable,” said Chesney, 57. “I have never really considered how many; just how much fun everyone’s having. But when you look at this list, see names of people who set the bar in so many ways, it takes your breath away.”
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He continued, “And a list like this? The numbers don’t lie. To think we played to over 18 million people since 2001—even with the time we had to take off—is mind-blowing for a kid from East Tennessee. But it says everything about the passion No Shoes Nation brings to this music.”
Elsewhere, Luke Bryan came in three spots ahead of Toby Keith at No. 20. Coldplay topped the list by a mile, followed by U2, Ed Sheeran, Dave Matthews Band, and Taylor Swift.
Featured image by Brett Coomer/Houston Chronicle
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