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A brawny singer-songwriter with piercing blue eyes and an Oklahoma twang, Mr. Keith cultivated a persona as “the big, bad outlaw who hides a big, soft heart,” as music critic Stephen Thomas Erlewine once put it. He could be ornery, cantankerous, self-deprecating and sensitive, recording mournful ballads about heartbreak and desire, as well as party songs about raising hell, drinking whiskey from a paper cup and getting high with his friend Willie Nelson.
His biggest crossover hit, “Red Solo Cup” (2011), was an endearingly goofy ode to the humble plastic drinking vessel — “the best receptacle for barbecues, tailgates, fairs and festivals” — which was sung in a quasi-drunken mumble and reached No. 15 on the Billboard Hot 100.
Mr. Keith also saluted the flag and the troops in hits like “Courtesy of the Red, White and Blue (The Angry American”) (2002), a post-9/11 morale raiser that generated controversy over its jingoistic lyrics, and “Made in America” (2011), a celebration of buying American-made goods and raising your children on “King James and Uncle Sam.”
That combination of flag-waving patriotism and beer-soaked good humor helped make him one of country music’s biggest stars, with 42 Top 10 hits on the genre’s Billboard chart, including 20 No. 1s. By the late 2000s, he was bringing in nearly $50 million a year, aided by business ventures that included a restaurant chain, a liquor brand, a Nashville record label and a stake in Big Machine Records, the label that signed Taylor Swift.
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