More New Country playing Dylan Marlowe - Boys Back Home (Feat. Dylan Scott)

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Country Music in the 90’s: The Year is 1999

Bobbycast

Monday, October 5, 2026 - 58 minutes

Bobby closes out his year-by-year journey through country music in the ’90s with 1999, the final chapter of a decade that completely reshaped the genre. He looks back at Shania Twain’s incredible run, Tim McGraw continuing to climb, new stars like Brad Paisley and Keith Urban beginning to emerge, and a handful of songs that would outlive the year by decades. Along the way, Bobby shares conversations with artists about the moments that changed their careers and revisits the pop culture, technology, and unforgettable events that made 1999 feel like the end of something special. It’s one last trip through the music, memories, and moments that defined country music in the ’90s.

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