These are twenty records that were released between 1956 and 1963 that I deem to be the best heartbreak songs of the era, ranked from #1 to #20.
Heartbreak Rank title artist week debuted highest ranking
1 Crazy Patsy Cline 11/6/1961 9
2 Crying Roy Orbison 8/28/1961 2
3 Since I Don't Have You The Skyliners 3/23/1959 12
4 Raindrops Dee Clark 5/22/1961 2
5 Since I Fell For You Lenny Welch 11/23/1963 4
6 Tears on My Pillow Little Anthony & the Imperials 8/18/1958 4
7 Mr. Blue The Fleetwoods 9/14/1959 1
8 I'm Sorry Brenda Lee 6/6/1960 1
9 The End of the World Skeeter Davis 2/16/1963 2
10 You Don't Know Me Ray Charles 8/4/1962 2
11 Will You Love Me Tomorrow The Shirelles 12/12/1960 1
12 I Fall to Pieces Patsy Cline 7/24/1961 12
13 Emotions Brenda Lee 1/16/1961 7
14 Among My Souvenirs Connie Francis 12/7/1959 7
15 All Alone Am I Brenda Lee 10/6/1962 3
16 Born To Lose Ray Charles 5/19/1962 41
17 There Goes My Baby The Drifters 6/29/1959 2
18 He Will Break Your Heart Jerry Butler 11/7/1960 7
19 Only the Lonely Roy Orbison 6/20/1960 2
20 Lonesome Town Ricky Nelson 10/20/1958 7
Brenda Lee leads with 8 A+ heartbreak songs -- three in the top twenty, my highest ranked being her most popular record, "I'm Sorry."

When love goes bad it's always been a common practice to turn to a song to assuage the melancholy. The Elvis Era had a good representation of heartbreak songs. Here are what I consider to be the twenty best of these breakup songs. Some great songs from the era have been excluded even thought they do express the proper sentiment because of their tempo. For example, Neil Sedaka's "Breaking Up is Hard to Do" should be a natural, but its fast cadence keeps it from truly expressing any heartache. Sedaka remade the song in 1975 as a ballad -- that version might have made the list.

The top ranked heartbreak song of The Elvis Era is a country song. Patsy Cline's "Crazy" was ranked #2 by Rolling Stone magazine on its list of the "100 Greatest Country Songs of All Time" published in 2014. Its expression of unrequited love is classic: "I'm crazy for trying, and crazy for crying, and crazy for loving you."

"Crying" by Roy Orbison is a close second. It literally has you wallowing in sadness: "you left me all alone, alone and crying." Two other entries in the top ten also have the tears flowing. In "Raindrops," Dee Clark tells us "they must be raindrops, cause a man aint supposed to cry." Little Anthony & The Imperials lament "Tears on my pillow, pain in my heart, caused by you."

Brenda Lee places a whopping three songs in the top twenty with "I'm Sorry" the top ranked at #8. Roy Orbison gets two with "Only the Lonely" barely qualifying -- some might dismiss it due to its tempo, but I think it still evokes the sadness of a heartbreak song even at its slightly increased pace. Ray Charles also has two on the list with "You Don't Know Me" his best at #10. Patsy Cline is another multiple with "I Fall To Pieces" joining "Crazy" on the list.

There are other heartbreak songs that I would also give an A+ rating, but to continue to split hairs and rank them is too taxing an effort -- therefore they are listed in alphabetical order.

Other A+ Heartbreak Records From The Elvis Era:
All I Have To Do Is Dream by The Everly Brothers 4/28/1958 #1
Are You Lonesome Tonight by Elvis Presley 11/14/1960 #1
As Usual by Brenda Lee, 9/19/1960, 12/28/1963 #12
Big, Big World by Johnny Burnette 5/6/1961 #
Blue On Blue by Bobby Vinton 6/1/1963 #3
Break It To Me Gently by Brenda Lee 1/20/1962 #4
Breaking In A Brand New Broken Heart by Connie Francis 4/24/1961 #7
Can't Get Used to Losing You by Andy Williams 3/23/1963 #2
Cry Baby by Garnet Mimms & The Enchanters 9/7/1963 #4
Cry to Me by Betty Harris 10/26/1963 #23
Crying in the Rain by The Everly Brothers 2/2/1962 #6
Don't Bet Money Honey by Linda Scott 7/24/1961 #9
Don't Break The Heart That Loves You by Connie Francis 2/24/1962 #1
Don't Think Twice, It's Alright by Peter, Paul & Mary 2/28/1963 #9
Don't Worry About Me by Marty Robbins 2/13/1961 #3
Fool Number One by Brenda Lee 10/9/1961 #3
Heartbreak Hotel by Elvis Presley 3/10/1956
I Cried a Tear by LaVern Baker 12/28/1958 #6
I Left My Heart In San Francisco by Tony Bennett 9/29/1962 #19
I Want To Be Wanted by Brenda Lee 9/19/1960 #1
I'll Never Dance Again by Bobby Rydell 6/23/1962 #14
I'm Leaving It Up To You by Dale & Grace 10/26/1963 #1
It Keeps Right On A Hurtin' by Johnny Tillotson 5/19/1962 #3
It's Only Make Believe by Conway Twitty 9/29/1958 #1
Just a Dream by Jimmy Clanton 7/21/1958 #4
Losing You by Brenda Lee 4/20/1963 #6
Moody River by Pat Boone 5/22/1961 #1
Only Love Can Break a Heart by Gene Pitney 9/29/1962 #2
Release Me by Esther Phillips 11/17/1962 #8
Running Scared by Roy Orbison 4/21/1961 #1
Sad Mood by Sam Cooke 12/19/1960 #29
She Cried by Jay & the Americans 4/7/1962 #5
She’s Got You by Patsy Cline 2/24/1962 #14
She's Not You by Elvis Presley 8/11/1962 #5
The Great Imposter by The Fleetwoods 10/2/1961 #30
The Great Pretender by The Platters 12/24/1955 #1
There She Goes by Jerry Wallace 1/9/1961 #26
Think Twice by Brook Benton 2/27/1961 #11
Those Oldies But Goodies by Little Caesar & the Romans 5/29/1961 #9
Tragedy by The Fleetwoods 5/8/1961 #10
True Love Never Runs Smooth by Gene Pitney 8/3/1963 #21
What Kind Of Fool Am I by Sammy Davis, Jr 10/6/1962 #17
Who's Sorry Now by Connie Francis 3/3/1958 #4
You Can Depend On Me by Brenda Lee 4/3/1961 #6
You Cheated by The Shields 9/15/1958 #12
You'll Lose a Good Thing by Barbara Lynn 7/14/1962 #8
You're The Reason by Bobby Edwards 10/16/1961 #11
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