When two powerful singers come together to tell a story, it makes the message that much more compelling.
In the case of these 23 sad country duets, that means that the heartbreak feels … well, twice as heartbreaking.
The bulk of this list is older country music, when duets between two established stars were more popular than they are today. Dolly Parton, Tammy Wynette and Reba McEntire are all among the stars who’ve put out multiple duets that were sad enough to make the cut.
But the heartbreak duet isn’t a lost art by any means.
Carly Pearce has found a groove as one of the country genre’s most powerful sad storytellers over the last few years, and she frequently joins forces with other artists to augment her music’s message.
Read More: These Are the Happiest + Saddest Songs in Country Music
More often than not, these sad songs share two sides of a breakup: His and hers.
Listeners get to feel the pain from both sides as a romantic couple go their separate ways, or yearn to get back together, even though their relationship might be doomed for good.
In two instances, though, this list sheds a different light on heartbreak, sharing perspectives from two women who are caught between the same man.
No matter what your vantage point is, these songs represent the best country music has to offer of two-narrative heartbreak.
In our No. 1 pick, that heartbreak even turns deadly. Read all the way to the end to find out which song made it to the top of this list of sad country duets.
The 23 Saddest Country Duets, Ranked
There’s just something about a duet that makes a sad song even sadder. With two different vocal perspectives and stories in play, the heartbreak just feels all that much more — well, heartbreaking!
Read on for Taste of Country’s list of all the saddest duets in country music history, and stay until the end to find out our No. 1 pick.
Gallery Credit: Carena Liptak
