George Strait could have been a farmer. At 28, the Army veteran was about to settle on a career in agriculture when he landed a recording contract in 1981. Twenty-five years on, it seems safe to say he made the right choice. Since his debut "Unwound" made it to No. 6, Strait, 54, has racked up 53 No. 1 singles and barely gone a month without a song on the charts. "He got popular when I was in high school," says Lee Ann Womack, who toured with Strait in '01. "Everybody would go to his concerts and dress like him—all of a sudden, country music became cool!" The key to his aw-shucks appeal? Colleagues say it's that he surrounds himself with old pals. "Most people on tour with George have been with him since he started," says Miranda Lambert, who toured with him earlier this year. "That keeps you humble. They don't treat him like 'George Strait'—they're friends with him."