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Playlists: songs about heartbreak

May 25, 2022 Peter Kimpton

Otis Redding - cut down in his prime


By magicman

Down at the end of Lonely Street: Heartbreak Hotel

I expected to be overwhelmed with music this week, and I listened to over 400 songs – now whittled down to 13 in the A-List, 13 in the B-list and 13 in the C-list. My cup overfloweth. There’s also a guru wildcard list at the end which is entirely unnecessary but there it is. Heartbreak comes in all shapes and sizes, each person’s experience is their own and I invite you to try and resist peeking downpage and just immerse yourself in the A-list before reading further. I know, you haven’t got time. But when you have – here’s the Heartbroken A-List : Turn it up, listen and weep…

Robert Johnson must open this sad soundtrack of tears, this valley of lost souls, this epic parable of tragedy and sorrow for he is eternal and poetic, simple and deep as the ocean. 

It always amazes me that Odyssey are not a simply huge legacy act – every time I hear this hit single and especially if I start to sing along, my eyes fill with tears and my throat gets tight. Beautiful lyrics, melody and what an under-rated singer Lilian Lopez is. Special.

Very little soul music was suggested this week, no Aretha, droplets of Al Green, no Stevie, no Four Tops, Tempts or Sam & Dave, no Gladys, Isaac, Nina Simone, blah blah blah but you know me, there’s enough to plant a little garden of sobbing heartache watered by the sweat and tears of the mighty Otis Redding.

Our beloved Landlord swooped in late with our Harry Nilsson and by then my standards were high – I’d already got an A-list and it had to be a cracker to dislodge one of those favourites – and yes, it’s a cracker. One of the great pop vocal performances of the 70s.

Over in Nashville they know how to write a sentimental song, but they also know how to live a life with some real-life material ready-made and waiting for a tune. Tammy Wynette’s marriage to George Jones was a double album of hits, and this is one of her very best. Pedal steel weeping into her vocal, outstanding.

Reparata & The Delrons had a small handful of hit singles before (I Am The) Captain Of Your Ship (aha) in 1968 and this is the best of them, perhaps not the finest single of the 1960s (we like a bit of big talk down at the Friday night Song Bar!) but this week they knocked the mighty Shangri-Las out of the number 6 position and make their first appearance in the Marconium. Long overdue I suspect.

And then 1971 Diana Ross. It just melts me. Suddenly I’m 14 again, never been kissed and trembling in a compassionate swoon over the lyrics to this heartbreaker of a song which evokes such feeling in a young man’s breast, and wait, look, I must still be that man because the song still works on me like a magic spell.

Angel Olsen was a popular pick in the opening hours of Song Bar and this song really got under my skin. It is not released at the time of writing, but will be on June 3rd. Shades of Lana, Skeeter and Marianne here, wonderfully atmospheric.

Sam Brown is the daughter of Joe Brown and this is her signature song which blew so many more popular and successful names out of the water this week – she sings it with great feeling and power and a direct authentic delivery that cuts through to this listener’s heart.

Hard to choose between a bunch of amazing early 60s shouts from the Everlys, Patsy Cline, George Jones, Etta James, poor old Johnny Ray and Dionne Warwick, Chuck Berry – all great, all worthy but no one wants a 90-song playlist. So Roy Orbison gets the nod this week because his vocal performance is so affecting that you get why he was in The Travelling Wilburys. Legend.

Roy Orbison - tragedy and tears behind the sunglasses

Jimmy Ruffin bless his heart was the older brother of David, who both travelled from Mississippi to Detroit to join the Motown stable and then Jimmy watched as David joined the Temptations – then he persuaded songwriters Witherspoon, Riser and Dean to let him sing this signature song (written for the Spinners) because he identified with the sentiments so strongly. A classic, with the Motown version of the classic Spector drumbeat and production.

Skeeter Davis led the most tragic life I have ever read about while making some of the most affecting and interesting country/pop tunes in the canon – also hugely influential on later artists with her slightly detached and damaged persona. She seems to be curious about her heartbreak in a way that therapists would encourage these days. And just breathe, because …

Here is the most devastating song of the week, and I suspect of all time, hiding in plain sight, and I guess if you know, you know. You know now. Taylor Swift wrote the song as a response to a blog she’d read by Maya Thompson whose three-year-old son Ronan died in 2011 of a neuroblastoma. Her response is a heart-wrenching piece of music that frankly made every other song I listened to alongside it sound trite and shallow. I toyed with putting this song in its own nuclear bunker but in the end it is the weight at the end of the rainbow, a true story of the heartbreak that we all must experience and the resilience that will get us through. 

From Wikipedia: “The pair met in October 2011, when Swift invited Maya to her concert in Glendale, Arizona. She wrote about her reaction when Taylor told her that she'd penned the song inspired by her blog entries, "My calmness soon turned to complete and utter frozen shock when these words came out of her mouth. 'I wrote a song for Ronan.'" Thompson added, addressing her late son, "'The tears started pouring down my cheeks as soon as I heard her say those words. But her words didn't stop there. Not only did she write a song for you, but she wanted to know if it would be alright to perform it on the nationally televised show.” Swift credits Thompson as the co-writer of the song. It was released to the US iTunes Store shortly after the Stand Up to Cancer telethon ended, and all proceeds of the single go towards cancer charities. 

The song blew me away.

Here’s a recap:

The Heartbreak A-List Playlist:

1. Robert Johnson – Love In Vain
2. Odyssey – If You’re Looking For A Way Out
3. Otis Redding – Pain In My Heart
4. Harry Nilsson – Without You
5. Tammy Wynette – Apartment Number 9
6. Reparata & The Delrons – I’m Nobody’s Baby Now
7. Diana Ross - I’m Still Waiting
8. Angel Olsen – Through The Fires
9. Sam Brown – Stop
10. Roy Orbison – Crying
11. Jimmy Ruffin – What Becomes Of The Broken Hearted
12. Skeeter Davis – The End Of The World
13. Taylor Swift – Ronan (Taylor’s Version)

So like I said I could’ve done three A-lists this week and in a way I did. At one point or another all of these songs below here were on the A-list, making way for the eventual garlanded winners with grace and poise. Thanks for playing, and thanks for listening. 

The Breaking Heart B-List Playlist:

1. The Bee Gees – How Can You Mend A Broken Heart
2. Eric Carmen - Never Gonna Fall In Love Again
3. Johnny Ray – Cry
4. Smokey Robinson & The Miracles – My Girl Has Gone
5. Hank Williams – Take These Chains From My Heart
6. Elliott Smith – No Name No. 5
7. John Mayer – Dreaming With A Broken Heart
8. Manic Street Preachers – You Stole The Sun From My Heart
9. The Shangri-Las – The Train From Kansas City
10. Earth Wind & Fire – After The Love Has Gone
11. Jun Togawa – Sayonara wo Oshiete
12. The Rankin Family – Fare Thee Well Love
13. Donny Hathaway – Giving Up


The Cardio Cracking C-List:

1. Janis Joplin – Cry Baby
2. Franco & TPOK Jazz – Ngai Tembe Eleka
3. Kenny Rogers – Ruby Don’t Take Your Love To Town
4. Daniel Johnston – You Put My Love Out The Door
5. Bruno Mars – When I Was Your Man
6. Mozart – Porgi Amor (Figaro)
7. Andi Thakambau – Isa Lei
8. Willie Nelson – Blue Eyes Crying In The Rain
9. John Holt – Left With a Broken Heart
10. Héctor Lavoe, Willie Colón – Ausencia
11. Stelios Kazantzidis – Efyge Efyge
12. Beck – Lonesome Tears
13. Deafheaven – Dream House

Guru’s Bonus Playlist:

(without any cry words except for some in German)

1. Richard Wagner - Tristan & Isolde prelude
2. J.S. Bach – Erbarme Dich (St Matthew Passion)
3. Brahms – Horn Trio in E-flat
4. Elgar – Nimrod
5. Samuel Barber – Adagio For Strings


Guru’s Bonus Playlist with Cry Words:

1. Ketty Lester – Love Letters
2. Gram Parsons – Love Hurts
3. Harold Melvin & The Bluenotes – Don’t Leave Me This Way
4. Marvin Gaye – Distant Lover (live)
5. Willie Nelson & Al Green – Rainin’ In My Heart
6. Nina Simone - Ne Me Quitte Pas
7. Jeff Buckley – Lover, You Should’ve Come Over
8. Amy Winehouse - Wake Up Alone
9. The Fureys & Davey Arthur – The Green Fields of France
10. Aretha Franklin - Don’t Play That Song
11. Wynona Judd – She Is His Only Need

These playlists were inspired by readers' song nominations from last week's topic: Tracks of more tears: songs about heartbreak. The next topic will launch on Thursday at 1pm UK time.

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Fancy a turn behind the pumps at The Song Bar? Care to choose a playlist from songs nominated and write something about it? Then feel free to contact The Song Bar here, or try the usual email address. Also please follow us social media: Song Bar Twitter, Song Bar Facebook. Song Bar YouTube, and Song Bar Instagram. Please subscribe, follow and share.

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In classical, blues, avant-garde, country, dance, folk, funk, gospel, indie, jazz, instrumentals, music, playlists, pop, rock, songs, soul, traditional Tags songs, playlists, heartbreak, relationships, bereavement, Robert Johnson, Odyssey, Otis Redding, Harry Nilsson, Tammy Wynette, Reparata & The Delrons, Diana Ross, Angel Olsen, Sam Brown, Roy Orbison, Jimmy Ruffin, Skeeter Davis, Taylor Swift, The Bee Gees, Eric Carmen, Johnny Ray, Smokey Robinson, Hank Williams, Elliott Smith, John Mayer, Manic Street Preachers, The Shangri–Las, Earth Wind & Fire, Jun Togawa, The Rankin Family, Donny Hathaway, Janis Joplin, Franco & TPOK Jazz, Kenny Rogers, Daniel Johnston, Bruno Mars, Mozart, Andi Thakambau, Willie Nelson, John Holt, Héctor Lavoe, Willie Colón, Stelios Kazantzidis, Beck, Deafheaven, Richard Wagner, JS Bach, Johannes Brahms, Edward Elgar, Samuel Barber, Ketty Lester, Gram Parsons, Harold Melvin & The Blue Notes, Marvin Gaye, Al Green, Nina Simone, Jeff Buckley, Amy Winehouse, The Fureys, Davey Arthur, Aretha Franklin, Wyona Judd
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