On this day in 1999, Brad Paisley celebrated his first chart-topper when his second song, "He Didn’t Have to Be," reached No.

1999 was an epic year in country music. Veteran hitmakers were still releasing music, arguably some of the best of their career, while relative newcomers were beginning to make their mark in the genre ...

Country music in 1999 looked a lot different from country music in the early 1960s, when Waylon Jennings began recording music under his own name. By the time the last year of the 20th century rolled ...