From incredible story songs to heartbreaking personal narratives, these 21 tracks share the saddest subject matter country music has to offer — from a female perspective.
Since the genre’s early days, women have released some of its best tear-jerking classics. Dolly Parton brought her unmatchable storytelling prowess to a song about a pregnant teenager, and Reba McEntire spoke about the devastation of AIDS, at a time when that topic was still mostly taboo.
The Chicks check in at No. 7 on this list with another story song, this one about the hometown heartbreak that happens during wartime. Their submission was a big country radio hit, but it got a little lost in the shuffle as the trio suffered massive backlash from their comments against U.S. president George Bush and the country’s invasion of Iraq.
Not all the songs on this list are stories written from imagined perspectives. Plenty of them share real-life heartbreak, too.
Read More: The Saddest Country Songs of the 2020s (So Far!)
Carly Pearce and Kelsea Ballerini both contributed songs to this list off recent projects — and both of those songs come from the singers’ respective divorce albums. Both singers opened up their heartbreak diaries as they were going through very public divorces, and fans cried along with them as the singers shared their most vulnerable moments and emotions.
But confessional-style sad songs aren’t limited to newer releases. In fact, our No. 1 pick for the saddest country song sung by a woman is a ballad that a legendary artist wrote about her troubled marriage. She recorded for the first time in the 1980s, with all-star backing vocals from Dolly Parton and Tammy Wynette.
Can you guess which song that is? Flip through the list below to find out.
The 21 Saddest Country Songs By Female Singers
So many of country’s most legendary sad songs have come from female artists. In this list, Taste of Country counts down the saddest songs with a female lead — of all time.
Gallery Credit: Carena Liptak
