The 21 Saddest Country Songs of the 2020s (So Far!)

The 2020s may only be halfway over, but already, this decade has produced a bumper crop of heartbreak songs and tear-jerkers.

Some artists opened up about their mental health struggles and childhood trauma; others put out albums documenting personal challenges — like divorces — in real time.

That authenticity in songwriting led to some sad songs that will likely stand the test of time, and eventually become staples of country music’s heartbreak catalog.

In particular, the 2020s has seen the rise of Jelly Roll: A performer known both for his musical talents and also for his powerful messages about addiction, incarceration and journey toward self-improvement. A star who speaks openly about his ongoing personal battles and his difficult road out of jail and toward success, Jelly inspired countless artists to be more open about their own stories.

Read More: The 20 Saddest Country Songs of the 2010s

The decade has also brought plenty of breakup songs, including releases from traditional-leaning artists like Scotty McCreery and Parker McCollum who are carrying the torch for the tear-in-your-beer, honky-tonk heartbreak hit.

Other more experimental artists, like Bailey Zimmerman, Koe Wetzel and Morgan Wallen, have offered new spins on the breakup song format, leading a classic country trope into a new era of the genre.

But the very saddest country songs of the 2020s share personal experiences with death. No. 1, No. 2 and No. 3 on our list of sad songs from the decade are all story songs about loss and grief, in three very different forms.

Keep reading for Taste of Country’s roundup of the saddest songs of the 2020s, so far.