The 20 Saddest Country Songs of the 1990s

The 1990s just might be the definitive era of sad country music.

For starters, some of the genre’s all-time best storytellers and vocalists were at the top of their game during this period. Acts like George Strait, Garth Brooks and Alan Jackson were releasing some of their career songs in the ’90s, and late legends like Naomi Judd and Joe Diffie were releasing the music we know and miss them for today.

At the same time, young bucks — like an at-the-time fledgling Tim McGraw — were just coming into their own as artists.

But it wasn’t just who was putting out music that made the ’90s such a great decade for sad songs in country music. Coming off the pop-inspired 1980s, the decade brought traditional country music back into fashion with a bang. That meant that storytelling — and tear-in-your-beer heartache — was hotter than ever before.

It’s the decade that produced canonic sad songs like Travis Tritt‘s “Anymore” and the Chicks‘ “Traveling Soldier,” and it’s also the decade where lesser-known stars like Sawyer Brown and Mary Chapin Carpenter put out the ballads that prove they deserve to be in enshrined in country music heartbreak history.

Scroll through the gallery below for Taste of Country’s round-up of the saddest songs of the 1990s, and see if our No. 1 pick matches yours.