90s Country: The Decade’s Best Songs About Heartbreak, and Lost Love

by Jacklyn Krol
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Country music brings all of the heartbreak and ache. Discover a list of the best songs from the 1990’s that cover every aspect of lost love.

Reminiscing on Breakups With Country Storytelling

“The Song Remembers When” – Trisha Yearwood

“The Song Remembers When” is a tale of a forgotten memory from a former romance that pops into one’s head when a song comes on the radio. The triggered memory makes her wonder why the relationship ended in the first place.

Trisha Yearwood recorded the song for her 1993 album with the same name. The song was written by Hugh Prestwood and was originally intended for another artist but was picked up by Yearwood for her third record.

“Who’s That Man” – Toby Keith

Toby Keith wrote and recorded “Who’s That Man” off of his 1994 alum, Boomtown. It became his second No. 1 on the Hot Country Songs Chart.

The song has an unusual take as it follows a man who returns home to see his ex-wife moved on. Once he sees him in his former home, he realizes that the new man has taken his place in the family.

“Can’t Really Be Gone” – Tim McGraw

“Can’t Really Be Gone” is another heartbreak anthem from McGraw. It details belongings of a former lover has left. He is trying to tell himself that she will be back and that she can’t stay gone.

The track was written by Gary Burr and was for McGraw’s 1995 record, All I Want. It reached No. 1 on the Billboard Country Singles Chart. The ballad has become a deep cut fan favorite.

“I Miss You a Little” – John Michael Montgomery

John Michael Montgomery wrote, “I Miss You A Little” alongside Richard Fagan and Mike Anthony. This marked the only songwriting credit he has on a single. It was the third single on his 1997 album, What I Do the Best. It reached No. 6 on the Hot Country Songs Chart.

The song has the narrator reflecting on his former lover who he keeps being triggered to remember his former flame. He realizes that he misses her more every day.

Songs About Trying to Change

“A House With No Curtains” – Alan Jackson

“A House With No Curtains” is a play on words as everyone knows that a couple is not happy in their relationship, and sees into their home. Alan Jackson sings about the pair that are still together even though they’re far from happy.

Jackson wrote the song with Jim McBride. It was a single off of his 1998 record, Everything I Love. It reached No. 18 on Billboard’s Hot Country Chart.

“I Can’t Do That Anymore” – Faith Hill

Surprisingly, “I Can’t Do This Anymore” was written by Alan Jackson and recorded by Faith Hill. It was a single off of her 1996 album, It Matters to Me.

The song tells the story of a woman who is trying to please her husband in countless ways. From cutting her hair to giving up her job, she tries it all just to make him happy. She comes to realize her worth and requires him to acknowledge what she’s done.

“When She Cries” – Restless Heart

“When She Cries” was written by Sonny LeMaire and Marc Beeson. Restless Heart debuted their recording in 1992 off of Big Iron Horses. The track reached No. 9 on Billboard’s Hot Country Singles Chart and No. 11 on the all-genre Billboard Hot 100.

The song is about a man who is with a woman who is going through a traumatic time in her life. He hopes to be the kind of man she deserves and to help her through this hard time in her life. Although it is not the traditional sense of heartbreak, it garnered attention from fans for the relatable twist on classic relationship struggles.

Country Heartbreak Classics

“The Fool” – Lee Ann Womack

Lee Ann Womack’s “The Fool” has stood the test of time. The ballad encounters another woman who once dated her lover who still has feelings for her. Womack initially passed on the song that was written by Marla Cannon-Goodman, Gene Ellsworth, and Charlie Stefl. The first version of the song was titled, “Which Way Is Left,” according to The Boot.

Additionally, it has since become a staple for her fans and was released on her debut album in 1997. It reached the No. 2 spot on the Hot Country Singles Chart.

“Today My World Slipped Away” – George Strait

“Today My World Slipped Away” was first recorded by Vern Gosdin in 1982. Gosdin co-wrote the song alongside Mark Wright. It was later covered by George Strait in 1997. His version reached No. 10 on the Billboard Hot Country Singles Chart. The song was off of his record, Carrying Your Love With Me.

Moreover, the song is about divorce and going straight from the courthouse to the church. Strait sings about the memories they had and trying to recover from having a family to being alone.

“For My Broken Heart” – Reba McEntire

Keith Palmer and Liz Hengber wrote, “For My Broken Heart.” The song was the title track off of her 1991 record. It reached No. 1 in the United States and Canada. Reba McEntire revealed in her biography, “Reba: My Story,” that the song was originally intended to be a duet with Clint Black.

In the song, a man breaks off a relationship. We find the woman believing that she can not go on before she takes a nap and wakes up realizing that life is continuing. The friend then realized that the world did not stop just because she had a broken heart.

“Every Light in the House” – Trace Adkins

Trace Adkins still hopes his ex will return and leaves every single light on in his house just in case she wants to come home. He hopes she’ll get tired of being gone but will slowly start turning each light off one by one if she doesn’t return.

Songwriter Kent Robbins penned the moving ballad. Adkins released the track on his 1996 album, Dreamin’ Out Loud. This marked his first Top 5 on the Hot Country Singles Chart as it reached No. 3.

“You Were Mine” – The Chicks (Formerly Dixie Chicks)

This 1998 single was a major success for The Chicks and their record, Wide Open Spaces. It topped the Country Singles Chart and reached No. 34 on the all-genre Billboard Hot 100 Chart. Additionally, it reached No. 3 on Canada’s charts.

Members and sisters Maggie Maguire and Emily Robinson wrote the song about a real-life experience. They wrote the song about their parents’ divorce.

So, what do their parents think of the song? “They know it’s about them, but [whispers] we never talk about it. [laughs] They don’t want to bring it up because they’re still weird around each other,” the sisters told Entertainment Weekly. “My dad doesn’t want to think it’s about him, because it doesn’t make him look very good, and my mom thinks she’s moved on.”

“Anymore’ – Travis Tritt

“Anymore” features Travis Tritt begging his ex to take him back. He doesn’t want to pretend that he doesn’t love her anymore, he wants to be able to express his true feelings and hope she feels the same.

Tritt co-wrote the song with Jill Colucci. Tritt debuted the song on his 1991 album, It’s All About to Change. He was able to achieve No. 1 status in the United States and Canada. Overall it was his second U.S. No. 1 and fourth No.1 in Canada.

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