Toby Keith wrote “How Do You Like Me Now?!” with Chuck Cannon right after finishing another song together, and Keith knew immediately he had something special, even though Cannon wasn’t so sure at first. It took them six months to circle back and finish it. When Keith submitted it to his label, he got disgusted looks in return, he later recalled being told the song crossed a line by having a woman cry while the narrator gloats, something typically reserved for songs about women getting revenge on men. Keith pushed back, insisting real life doesn’t work that way, and released it anyway after leaving Mercury Records for DreamWorks. It spent five weeks at number one and became the best-selling country song of 2000, launching the bolder, more swaggering persona Keith would carry for the rest of his career.

Introduction THE SONG THEY THOUGHT WENT TOO FAR BECAME TOBY KEITH’S BIGGEST BREAKTHROUGH Sometimes, the...