50 Musts for Your Old School Playlist


This list of 50 essential ’90s country music hits brings all kinds of warm feels.

The simplicity, the melodies, the head-jerking turn toward pop music and the mullets … it’s all here, and it’s all a wonderful trip down memory lane.

It’s possible this list of great 1990s country songs is also some sort of primer to understanding the decade, but no one is taking a college course on ’90s country music (yet), so we’ll just present these 50 songs as the best the decade offered. There are 50 songs by 50 different artists here — you’ll only find one song from Garth Brooks, Trisha Yearwood and Brooks & Dunn (three definitive ’90s hitmakers), because lesser-known singers like Daryle Singletary, Rick Trevino and Joe Diffie are equally important in defining what country music fans stood for in the 1990s.

The big pop shift happened in about 1996, led by women like Shania Twain and Faith Hill, plus male groups like Lonestar. A familiar homogeny is interrupted by ’90s hits by the Dixie Chicks, Dwight Yoakam and Trace Adkins. Some of today’s biggest stars (we see you Tim McGraw) got their start in the 1990s, but to compare Brad Paisley of 1999 with Brad Paisley of today is to compare a boy to a man!

Push play on the above playlist and slide through our list of 50 Essential ’90s Country Songs to learn more about a decade intent on making a comeback in 21st century America.

50 Essential ’90s Country Songs:

See 50 Essential ’90s Country Songs





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Graham Haring

Graham Haring is a versatile writer with a knack for capturing the heart of country music and the stories that surround it. Covering everything from new song releases by icons like Tim McGraw to unexpected cultural phenomena like "The Waffle House Index," his articles bring a mix of humor, depth, and curiosity to the table. Graham’s work often explores the personal side of country music, highlighting the community, family moments, and heartwarming stories behind the headlines. Whether it’s about Keith Urban's benefit shows or a quirky note from the past, Graham's writing resonates with country fans who appreciate a touch of authenticity and a good story.

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