Toby Keith Toby Keith’s breakout hit was “Should’ve Been a Cowboy.” True False None Toby Keith served in the U.S. military before becoming a country star. True False None “Red Solo Cup” was one of Toby Keith’s most successful and surprising party hits. True False None Toby Keith started his own record label after clashing with major labels. True False None Toby Keith is a member of the Country Music Hall of Fame. True False None Time's up Most Popular Most Popular