Whether you prefer the sad songs of the 2000s or the 2010s is ultimately going to come down to a matter of taste.

During the first decade of the millennium, big changes were afoot in country music. Darius Rucker moved into country stardom from the rock format. Carrie Underwood became a star on American Idol, and then found fans across the country, pop and gospel bases.

The genre started expanding its boundaries, its sounds and styles

Still, the solid neo-traditional stylings of the '90s were very much in play: Legends like George Strait and Garth Brooks remained active and were still finding hits with their signature brands of old-school twang. Sure, the genre was making steps toward experimentation, but the 2010s brought a downright explosion of it.

Taylor Swift, Luke Bryan, Thomas Rhett and Luke Combs were just a few of the artists who dominated the scene in the 2010s, proving that — more than ever — there were more ways than ever to achieve success in the genre, no matter your stylistic leanings.

That was true for song styles, too. In the 2010s, the country genre revamped the definition of what a sad song can be. Sure, there were still plenty of traditional heartbreak ballads, but the genre also broached devastating new topics, like cancer, infertility, parent and child death.

But no matter whether you prefer the solid-country 2000s or the sonically experimental 2010s, one thing's for certain: In each decade, our No. 1 pick is a weeper. Scroll through the lists below to compare and contrast, and see which one you think is sadder.

The 20 Saddest Country Songs of the 2000s

The 2000s delivered some of country music's stone-cold saddest songs, ever. Read on for Taste of Country's round-up of the biggest and best weepers of the decade.

Gallery Credit: Carena Liptak

The 20 Saddest Country Songs of the 2010s

Gallery Credit: Carena Liptak

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