In 1981, Ricky Skaggs had his first solo hit single at radio, with “Don’t Get Above Your Raisin’.” Throughout the 80s, Skaggs had hit after hit at radio, with songs like “Country Boy”, “Cajun Moon”, and more.
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But not all of his songs were happy ones. These are three Ricky Skaggs songs from the 80s, which are unbelievably sad.
“Crying My Heart Out Over You”
The only thing sadder than a broken heart is knowing that the pain is self-inflicted. It’s what Skaggs sings about in “Crying My Heart Out Over You”. Written by Lester Flatt, Earl Scruggs, Carl Butler, and Earl Sherry, the song first came out as part of the Flatt & Scruggs duo.
“Crying My Heart Out Over You” says, “Off somewhere the music’s playing soft and low / And another holds the one that I love so / I was blind, I could not see / That you meant the world to me / But like a fool I stood and watched you go / Now, I’m crying my heart out over you / Those blue eyes now they smile at someone new. / Ever since you went away / I die a little more each day ‘ Cause I’m crying my heart out over you.”
It might be a sad song, but it wasn’t for Skaggs. “Crying My Heart Out Over You”, out in 1981, became his first No. 1 hit.
“Don’t Cheat In Our Hometown”
Even the title of “Don’t Cheat In Our Hometown” is devastating. Written by Ray Pennington and Roy E. Marcum, “Don’t Cheat In Our Hometown” is the title of Skaggs’ sixth studio album.
Released as a single in 1983, the song begins with, “Tonight my heart is beating low and my head is bowed. You’ve been seen with my best friend on the other side of town / I don’t mind this waiting, don’t mind this running ’round / But if you’re gonna cheat on me, don’t cheat in our hometown.”
Skaggs reportedly tried to not do cheating songs. Still, he felt this one had more of a sad meaning than a meaning that went against his spiritual beliefs.
“I’ve Got A New Heartache”
In 1986, Skaggs released “I’ve Got A New Heartache”. A Top 10 single, the song appears on his live album, Live In London. “I’ve Got A New Heartache” is written by Ray Price and Wayne Walker. Price had a Top 5 single with “I’ve Got A New Heartache”, which he released in 1956.
The sad song says, “You’re back in town again, spreadin’ talk around / That I’m still in love with you, though you let me down / I hate to admit it but I guess the talk is true / Or else you couldn’t make my heart ache the way you do / I’ve got a new heartache about an old sweetheart / That left me for somebody new / I’ve got a new heartache about an old sweetheart / And that’s why I’m feeling so blue.”
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