In the 1980s, more than ever before, country artists and songwriters were perfecting the art of the story song. They learned to draw fans with a gripping narrative — and often, that made already sad songs even more compelling and tragic.

Stars like Reba McEntire, Willie Nelson, George Strait and George Jones are just a few of the artists who contributed incredible story songs to this list, making more a whole lot of compelling country music that has stood the test of time.

All of these songs are heartbreaking in their own way. Here, you’ll find songs about unrequited or ill-fated love, songs about remorse, and even one or two anticipatory songs about looking down the barrel of heartbreak.

No matter which way you slice it, this decade was home to some of the greatest lyrical masters in country music history — and their music is still pulling on our heartstrings, four decades later.

Scroll through the gallery below to see Taste of Country’s roundup of the saddest songs of the 1980s. Our No. 1 pick is a song that isn’t just the saddest song of the decade — it might be the saddest country song of all time!