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Signed to Nashville DreamWorks in 1998, Keith released his breakthrough single " How Do You Like Me Now?!

" that year.

This song, the title track to his 1999 album of the same name, was the Number One country song of 2000, and one of several chart-toppers during his tenure on DreamWorks Nashville.

His next three albums, Pull My Chain, Unleashed, and Shock ' n Y'all, produced three more Number Ones each, and all of the albums were certified multi-platinum.

A second Greatest Hits package followed in 2004, and after that, he released Honkytonk University.