The 20 Saddest Country Songs of the 2000s

The 2000s delivered some of country music’s stone-cold saddest songs, ever.

Want proof? Brad Paisley and Alison Krauss‘ “Whiskey Lullaby” — one of country music’s defining heartbreak ballads, and a staple of the format’s modern era — only clocked in at No. 2 on this list of sad country songs from the decade.

In terms of weepers, the 2000s provided a little bit of everything. Heartbreak is well-represented here. So are songs about fallen war heroes and young love cut tragically short by a war casualty. On this list, you’ll also find songs about cancer, death, abuse and more tough topics.

But the saddest songs of the ’00s also included a handful of great tracks that are bittersweet: Either because they describe the pain of a natural, positive life change, or because they’re reminders to live each day to the fullest.

Read on for a round-up of heavy-hitting modern-day classics, from great artists like Alan Jackson, Trace Adkins, Martina McBride, Johnny Cash and many others.