Top Touring Acts Tweet Posted May 28th, 2014 @ 4:16am Which artists represent country on Billboard's list of "Top 25 Live Artists since 1990"? None other than Kenny Chesney, George Strait and Toby Keith! Kenny comes in 9th, grossing more than $752 million in ticket sales. George pulled in more than $405 million, placing him in 19th place. Toby shows up at #22, having grossed more than $361 million. In first place overall- The Rolling Stones, who have made over one & a half BILLION dollars since 1990!