Trisha Yearwood Names Her Top 5 Country Heartbreak Songs of All Time

Trisha Yearwood
Courtesy Everett Collection

Trisha Yearwood in the 1990s.

Who knows a great country song better than Trisha Yearwood? “She’s in Love With the Boy” kicked off her career in 1991 by making her the first female vocalist since Connie Smith in 1964 (“Once A Day”) to top the chart with her debut single. Since then, Yearwood has added to laurels such classic moments as “Walkaway Joe,” “The Song Remembers When,” “How Do I Live” and the haunting “Georgia Rain.” So when Billboard was looking for an artist to ask their five favorite country heartbreak songs of all time, Yearwood was at the top of the list -- and just like she has done as an artist, she picked some very good ones.

See the All-Time Country Charts and Other Top Breakup Songs: Country Artists | Country Songs | Country Albums | Top 30 Breakup Songs

1. “Chiseled in Stone," Vern Gosdin: “Any song Vern Gosdin sings cuts to the core, but this song is the ultimate heartbreak song… I mean, the lyrics, 'you don’t know about lonesome … til it’s chiseled in stone.' It doesn’t get sadder than that.”

2. "D-I-V-O-R-C-E," Tammy Wynette: “Spelling the sad words so her little boy won’t understand what’s happening to their family… heartbreaking. And to hear the cry in Tammy’s voice makes me want to cry.”

3. “He Stopped Loving Her Today," George Jones: “This song is on everybody’s list for everything great about a country song, but it was brilliantly written by Bobby Braddock. The poor guy in this song has to die to get over this woman. George Jones? Well, he’s the king. Nobody could have sung it better.”

4. “Sunday Morning Comin’ Down," Kris Kristofferson: "I love Kris Kristofferson’s version, because it just feels like he’s living it in the moment. 'There’s something 'bout a Sunday, that makes a body feel alone.’ I love this poignant, sad song.”

5. “Whiskey Lullaby," Brad Paisley & Alison Krauss: “Heartbreak, alcohol, suicide and a haunting melody make this song one of the saddest I’ve ever heard.”

Billboard Greatest of All Time

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