These 3 Country Songs From 1989 Are Among the Saddest Tunes Ever

Few country songs stand the test of time like sad songs. The entire genre is built on songs that evoke strong emotions, including these three country songs from 1989, which are among the saddest country songs ever released.

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“The Lonely Side Of Love” by Patty Loveless

“The Lonely Side Of Love” might be an uptempo Patty Loveless song, but the message is heartbreaking. Written by Kostas, “The Lonely Side Of Love” is about someone who found themselves alone, after thinking they had found someone they would spend the rest of their life with.

“The Lonely Side Of Love” is on Loveless’s third studio album, Honky Tonk Angel. The song says, “What makes two people / Fall in love / What good’s a promise / When the love is gone / Where do you go / When you find yourself / On the lonely side of love.“

“The Lonely Side Of Love” became a Top 10 hit for Loveless. It comes right after “Timber, I’m Falling In Love”, which is the first No. 1 hit of her career.

“Where Did I Go Wrong” by Steve Wariner

Steve Wariner wrote “Where Did I Go Wrong” by himself for his I Got Dreams record. The song says, “Where did I go wrong / Where did he go right / I know I’d won the battle, if I’d known there was a fight / I can’t stand the thought of never holding you tight / Where did I go wrong, he go right.”

According to Classic Country Music Stories, Wariner wrote “Where Did I Go Wrong” while on tour with Reba McEntire. The song became Wariner’s eighth No. 1 single of his career.

“I Wonder Do You Think Of Me” by Keith Whitley

” Wonder Do You Think Of Me” is perhaps Keith Whitley’s saddest song, and not just because of the message. Written by Sanger D. Shafer, the song came out in June of 1989, the first single released after Whitley passed away on May 9 from acute alcohol poisoning.

The title track of Whitley’s third, and final, studio album, the song says, “If you drive around back in our old hometown / I wonder, do you think of me / When you drive by a school, do you remember two fools / I wonder, do you think of me / And remember the park where you struck the spark / To a fire that’s still burning oh, in my heart / That old graduation day you just drifted away / I wonder, do you think of me.”

“About 1986, I came up with that song,” Shafer says (via Songfacts). “Keith was gonna put it out as a single, regardless of the circumstances, but it’s kind of ironic the way it is now. It kind of hits the nail on the head.”

The follow-up single, “It Ain’t Nothin’”, became Whitley’s final No. 1 single of his career.

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