Reinventing himself on a new record label, Toby Keith had the last laugh when “How Do You Like Me Now?!” spent five weeks at No. 1 in March and April 2000. It wasn’t exactly a comeback, because Keith had done incredibly well for himself on Mercury Records in the ’90s. Just as the song says, he was indeed “living in your radio” with a string of chart-topping hits he wrote.
However, with a shift to DreamWorks Records, he could express himself far more freely. His rugged attitude and willingness to put his personality at the fore endeared him to millions of country listeners, who followed him through another decade of No. 1 hits.
His own smirking sense of humor is evident in the “How Do You Like Me Now?!” video, as he invites an unrequited former crush to meet him at midnight at the football stadium — only to rub it in her face that she was wrong (with a cheer routine, no less).
Keith’s platinum-certified 2000 album, also titled How Do You Like Me Now?!, won an ACM Award, while Keith picked up a Male Vocalist trophy that same year. So, guess that answers that question.