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10 Jean Shepard Hit Songs For A Love-Heavy Rotation

Jean Shepard Songs

When Jean Shepard was making her way into the country music scene, she never felt the need to fit herself into the mold. She won people over with her rather unfamiliar hard-edged honky tonk vocals – unlike the usual smooth singing. And she was unafraid to record and release gritty songs, which were mostly about love from the point of view of women, like “Forgive Me, John,” “A Dear John Letter,” “I Thought of You,” and many more. It was she who opened the door for artists like Loretta Lynn to explore themes that record labels would’ve otherwise nixed. 

And so, to celebrate her feisty decades-long career, we’ve compiled 10 Jean Shepard hit songs that you should definitely add to your love-heavy rotation. 

1. “A Dear John Letter”

From A Dear John Letter (1953)

This track played on the Dear John letters, which debuted in 1943 during World War II. In the story, a young woman writes of her cold love for him. To add to the heartbreak, she also told him that she would be marrying his brother instead. While this was an emotionally complex song to deliver, 19-year-old Jean Shepard nailed the song with ease, along with her duet partner Ferlin Husky (who provided recitation parts). 

“A Dear John Letter” shot to number one on the country charts, holding it for six weeks during its 23-week chart run. It also made her the youngest female artist to earn a chart-topper, a record she held for 20 years until 14-year-old Tanya Tucker arrived with “What’s Your Mama’s Name.”

2. “Forgive Me, John”

From A Dear John Letter (1953)

Their follow-up duet, which Shepard co-wrote, was another letter to John. This time, it was a realization of her mistake – she loved him still and that he was the only one for him – and she wanted to ask for his forgiveness. But John ultimately decided he didn’t want her back. 

While it wasn’t a chart-topper, it was still another big hit for the duet partners, earning them a ticket to Bakersfield and Los Angeles country scenes as well as an opportunity to tour. 

3. “I Thought of You”

From B Side of “Beautiful Lies” (1955)

After Shepard made her breakthrough as a solo artist with her rendition of the Joe “Red” Hayes and Jack Rhodes penned track “A Satisfied Mind,” she enjoyed a string of chart hits, including “I Thought of You.” The track was originally written by Jimmy Rollins, which he first copyrighted in 1955. 

This Top 10 B-side was straightforward and honest, probably to a fault. That is, the woman told her previous partner that she still saw him even though she was in another man’s arms. 

4. “Girls in Disgrace”

From Songs of a Love Affair (1956)

This list wouldn’t be complete without an entry from Shepard’s debut studio album, dubbed as the genre’s first concept album in history and the first by a female country artist. 

The song was written by Mary McDaniel and Dan Welch, who also wrote another track in the album called “Over and Over.” And it talked about a failed promise of a man to a woman to marry her. And so, the woman became the talk of a gossiping town and a girl in disgrace. 

5. “The Root of All Evil (Is A Man)”

From The Best Of Jean Shepard (1963)

While many believe the old story that money is the root of all evil, Shepard sang, “Well let me tell you mine it’s much older than time for the root of all evil is a man.” And that was because they’d tell you they love you, only for you to find out you weren’t the only one. 

And so, she was telling all the girls to heed her advice and think things over before committing to a man. 

6. “Second Fiddle (To An Old Guitar)”

From Heart, We Did All We Could (1964)

“Second Fiddle (To an Old Guitar)” was definitely a memorable song on Shepard’s discography as it was her comeback song after her first husband, Hawkins, died in a plane crash. 

She had put her career on hold for several months, and then, in 1964, she came back strong with a Top Five hit song about a man who looked at his guitar with a love that he could never show her. And she was tired of this love affair. To make it even more precious, it was her first charting record since 1959. 

7. “Many Happy Hangovers to You”

From Many Happy Hangovers (1966)

In Shepard’s vocabulary, men fall in love with three things: another woman, a guitar, and a bottle. 

Written by Johnny McRae, this song confronts a wayward husband who holds the bottle longer than he holds his wife. And she knew he would wake up sick with bloodshot eyes, alone and lonely, and with a note saying, “Many happy hangovers to you.”

8. “Then He Touched Me”

From A Woman’s Hand (1970)

Shepard has always placed a song on the charts, and in 1970, she had “Then He Touched Me.” The song, penned by George Richey and Norro Wilson, was a sensual story of a woman who had already given up on love. And then, she found someone who turned that around, singing, “When he kissed me my lips started burnin’ once again. When he held me my feet just wouldn’t touch the ground.”

It peaked at number 8 on the charts. 

9. “Another Lonely Night”

From Here and Now (1971)

Penned by Jan Crutchfield, this track was excruciatingly painful. It talked about a vulnerable woman who, despite her partner cheating on her time and time again, still found the strength to give him another chance. The song reached number 12 on the charts. 

10. “Slippin’ Away”

From Slippin’Away (1973)

This Anderson-penned tune marked a new era in Shepard’s music career. “Slippin’ Away” was her first single when she signed with United Artists Records in 1973. But the song itself was a mark of an end – a last-ditch effort to save a marriage that had already been slippin’ away. 

The song hit number 4 on the charts, her most significant position on the charts in a decade. It would also be her last top-10 hit. 

That’s a wrap on Jean Shepard’s songs. Make sure to listen to every single one!

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