Top Eleven Heartbreak Songs of All Time

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Sep 21, 2000 (Updated Nov 10, 2000)




After reading and enjoying several reviews in the recent Top Ten Heartbreak Songs Write-off, I was inspired to add my own listing of favorite "Heartbreak" songs. I’d like to define what I believe constitutes a great heartbreak song. First, the song MUST have a beautiful melody, second, it MUST have memorable, emotional, poetic lyrics, and third, it should to be about unrequited love, lost love, or betrayed love. The singer must "yearn" achingly for the lover who has betrayed them for another, or wish and hope with all their heart to be noticed by the object of their love. Saddest of all, are songs where death, great sacrifice, or circumstance has robbed the singer of the love they treasured.

I have been married to the love of my life for almost thirty years, so I know nothing about the heartbreak of love lost. I do have dim memories of unrequited love. Miss Pope, my third grade teacher at Eugene Field Elementary School, was my first true love. She was twenty two (and married) I was eight, it was doomed from the start. Here is the list in no particular order.

1.) "I Fall to Pieces" by Patsy Cline from Patsy Cline “Greatest Hits” This is probably the number one heartbreak song of all time. In 1960 Patsy Cline had been working in Nashville for five long years, struggling to make it as a country singer. She had only one small hit “Walking after Midnight” to her credit. Her producer (Owen Bradley) got hold of ”I Fall to Pieces” after three male country legends had turned the song down, "too feminine" for a guy to sing was the reasoning. When Patsy heard that three famous singers had turned the song down, she refused to even consider singing it, saying “I won’t be anybody’s fourth choice”. Bradley begged her to record the song, and finally she relented and went into the studio, unhappy, eight months pregnant, and impatient to be finished. She recorded the song in less than forty five minutes with no rehearsal. “I Fall to Pieces” was an instant hit (on both the country and "pop" charts) and the song made Patsy a major star, she was killed two years later in a plane crash.

2.) “I Will Always Love You” by Dolly Parton From Dolly Parton “Greatest Hits” Dolly’s song is a plaintive, simple, and honest country ballad that explores the heartbreak of the ultimate sacrifice. She will always love him, but she knows that she is not what he needs, so she gives him up. The song is like a "goodbye" letter to the love of your life. Dolly's "original" is much better than Whitney Houston’s anemic remake from the “Bodyguard” soundtrack.

3.) ”Love Hurts” by Gram Parsons and Emmylou Harris from Gram Parsons “Grievous Angel” This song was written by Felice and Boudleaux Bryant, the songwriting team who created many of the Everly Brothers most popular hits. The Gram Parsons & Emmylou Harris version of this song is a perfect example of Parson's at his very best, an achingly beautiful, simple, honest, and heartbreaking tune. Parsons was one of the primary architects of the "Country Rock" sound that influenced many seventies groups, including the Flying Burrito Brothers, the Byrds, the Eagles, the Grateful Dead, and Elvis Costello. Parsons died (at age 26) soon after "Love Hurts" was recorded.

4.) “Only the Lonely” by Roy Orbison from “All Time Greatest Hits of Roy Orbison” With lines like, “Only the lonely know how I feel tonight, only the lonely know this ain’t right” this song couldn't miss. Add Orbison’s gorgeous voice and incredible delivery and "Only the Lonely" was an instant classic. Orbison, like Elvis Presley, Carl Perkins, Jerry Lee Lewis, and Johnny Cash got his start at Sam Phillip's legendary Sun Records in Memphis.

5.) “All I have to do is Dream” the Everly Brothers from “The Everly Brothers Greatest Hits” With a hook like "Gee Whiz, I'm dreamin' my life away" this song caught the innocence and purity of young love perfectly. The Everly's learned to sing and play from their father, a Preacher in Western Kentucky. They influenced dozens of groups like Crosby, Stills, & Nash, The Grateful Dead, the Eagles and the Byrds, with their beautiful harmony vocals.

6.) “Cry to Me” by Solomon Burke from the “Dirty Dancing” Sountrack, Volume Two Although he is almost forgotten today, Burke was very popular in the sixties. This song was covered by the “Rolling Stones”. Burke is another performer who grew up singing in church, and his gospel roots are evident in "Cry to me"

7.) “If I Could Only Win Your Love” by Emmylou Harris from Emmylou Harris “Pieces of the Sky” This Charlie and Ira Louvin composition is one of the purest Country/Bluegrass ballads ever written, it sounds like something the Carter Family might have recorded. The bouncy upbeat music and "Yearn for you" lyrics never fail to leave a smile. Classic "unrequited love" song, Harris' voice hasn't sounded truer since her days with Gram Parsons.

8.) “Can’t Undo What’s Been Done” by Steve Kolander from “Steve Kolander” I bought this one in Japan after hearing “Can’t Undo What’s Been Done” and "Listen to Your Woman” in a small Coffee House in Naha, Okinawa.. Kolander’s straight ahead rock-a-billy musical style, crystal clear voice, and the poetry of the lyrics are absolutely mesmerizing. Classic betrayal song.

9.) “Teardrops” by Womack & Womack from Womack & Womack “Conscience” "Teardrops on the dancefloor, remind me, baby, of you, I look down and cry, next time I'll be true" Linda Womack is the daughter of the great Sam Cooke (Another Saturday Night, Soothe Me, and A Change is Gonna Come) genetics show, she is an incredibly talented singer, with a fantastic voice. Her husband Cecil Womack started his career, as a teenager, playing in Cooke’s band (along with brother Bobby). Strangely enough, Womack & Womack are much more popular in Europe than they are in the U.S. Bonnie Rait & Delbert McClinton covered one of their songs (Good Woman/Good Man) and won a grammy. Much as I like both Rait and McClinton, the Womack’s version is better.

10.) “You Can Say What You Want” by Texas from “White on Blonde” Sharleen Spiteri’s vulnerable “little girl” voice enhances and adds a mystical element to the musical power of this Glascow, Scotland group. Together for more than a dozen years, the group concentrates on consummate musicianship and timeless lyrics about real issues. Spiteri’s vocals are spellbinding, and her delivery is always right on the money.

11.) "Somebody's Cryin'" by Chris Isaak from Forever Blue This is one of the best "unrequited love" songs ever. Isaak's incredible rock-a-billy vocal really tugs at the heartstrings, "I know somebody and they cry for you, they lie awake at night and dream of you, I bet you never even knew they do, I know somebody and they call your name, a million times and still you never came, they go on loving you just the same" Chris Isaak is often called the legitimate successor to Elvis Presley and Roy Orbison





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