Dolly Parton: Her Top 10 Most Heartbreaking Songs

by Jacklyn Krol

Dolly Parton sure knows how to pack on the emotion with her music. Discover her top ten most heartbreaking songs, below.

10. “Release Me”

Album, Year: Heartbreak Express, 1982

“Release Me” was co-written by Parton and Greg Perry. Fittingly, the song was released on her album with the heartbreak theme. She begs her significant other to let her go because the relationship no longer has love.

9. “Heartbreak Express”

Album, Year: Heartbreak Express, 1982

Parton’s 1982 album of the same name was based around this single. In the song, she says goodbye to a relationship that didn’t work out and embarks on the ‘Heartbreak Express.” Her storytelling skills shine on this tune and the music videos proves just how emotional and eye-catching she is as a performer. Parton wrote the song solo and it reached No. 1 on the Canadian RPM Country Chart and No. 7 on the U.S. Hot Country Songs chart.

8. “Barbara on Your Mind”

Album, Year: Jolene, 1974

Although “Barbara on Your Mind” is not a hit single, it does deserve recognition. The song tells the story of a woman discovering that her husband is cheating. He accidentally called his wife Barbara. He told her sweet words of love that she had not heard in a long time while knowing that the other woman was on his mind.

7. “Games People Play”

Album, Year: My Blue Ridge Mountain Boy, 1969

Parton is known to be an excellent songwriter, it did come as a surprise when she released a cover of a song. She released “Games People Play” which was originally written and recorded by Joe South in 1968. It won the Grammy Award for Song of the Year and Best Contemporary Song that year. Later on, Parton created a stunning country tune out of the original rock song.

6. “What a Heartache”

Album, Year: Rhinestone, 1984

The song was featured in the 1984 movie that Parton starred in alongside Sylvester Stalone, Rhinestone. She sings about someone that she believed would be forever and turning out to be a major heartbreak. The lyricism shines on the song, “It just goes to show that you never can tell / I really thought that I knew you well / I still can’t believe I could be deceived so easily.”

5. “Prime of Our Love”

Album, Year: Heartbreak Express, 1982

This song screams heartbreak. The tune tells the story of Parton taking care of her man and doing all she can for him. He ends up leaving her in the prime of their love. “In the prime of our love you’ve forsaken / Our bright hopes and just left them to fade / And the heart that was yours for the breaking / Lies in pieces to wither away / Lies in pieces as cold as the clay,” she sings.

4. “Just Someone I Used to Know” – Dolly Parton and Porter Wagoner

Album, Year: Porter Wayne and Dolly Rebecca, 1970

Firstly, “Just Someone I Used to Know” was originally recorded in 1962 by George Jones. At the time, it reached No. 3 on Billboards Top Country Singles chart. Secondly, Jones collaborated with his wife, Tammy Wynette for a duet rendition. Finally, in 1969 Porter Wagoner and Parton decided to add it to their fourth studio album. The record itself reached at No. 4 on Billboard Top Country Albums chart as well as Billboards Top 200.

Overall, the song peaked at No. 5 on the Billboard Hot Country Songs chart and No. 20 on the Pop Singles chart. The song became a success because of the lyricism and their emotional performance with one another. The song talks about looking in your wallet and finding a picture of a former flame and reminiscing but not admitting that he loved the person.

3. “Do I Ever Cross Your Mind”

Album, Year: Various

Parton sings about wishing she was able to go back in time and wondering if her former flame still thinks about her the way she does about him. The song was first recorded in 1976 as a duet with Chet Akins on his album, The Best of Chet Atkins & Friends. Parton recorded a solo version on Heartbreak Express in 1982. Finally, in 1999, she recorded a version with Emmylou Harris and Linda Ronstadt on the album, Trio II.

2. “I Will Always Love You”

Album, Year: Various

I Will Always Love You” is a beautiful love song, yes, but the lyrics are utterly heartbreaking if you look at it from another point of view. The inspiration for the song came about when Parton leaving her longtime television show and duet partner, Porter Wagoner. She even performed the song for him to say goodbye. The tune was originally released on Parton’s Jolene album in 1974.

Her version first peaked at No.1 in June of 1974. She later re-recorded the song for the film, The Best Little Whorehouse in Texas in 1982. It reached No. 1 once again. Only a handful of artists have managed to secure two No. 1 singles for the same song.

Whitney Houston recorded her rendition for the soundtrack of the film, The Bodyguard. In 1992 it reached No. 1 on the all-genre Billboard Hot 100 chart for (at the time) a record-breaking 14 weeks. It is one of the best selling songs of all time. Countless artists have covered the song and the tune has been performed in almost every genre of music.

The No. 1 Dolly Parton Heartbreak Song

Album, Year: Jolene, 1974

Obviously, the iconic hit “Jolene” takes the cake. Dolly Parton sings about a woman who could easily take her husband and begs her not to try because she knows that if she does, she will succeed at taking him.

Arguably, this is one of the most well-known country songs of all time. Parton named her album after the single. Countless artists of all genres have released covers of the song like Miley Cyrus, Pentatonix, Kelly Clarkson, Olivia Newton-John, Norah Jones, among others.

Believe it or not, Jolene is not an actual person, the inspiration came from two people. Parton used the looks of a fan that she met to describe the character while the story came about from a bank clerk who flirted with her husband.