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Hurts So Good - My Favorite Songs of Heartache & Heartbreak

GaybreakupI haven't had my heart broken very often.  Truth be told, more often than not I've been the one who's been the heart breaker.  Still, only by having loved and lost can one truly appreciate songs that convey the pain of heartache.  For moments like that I created a playlist on my iPod called "Despair" that has close to 250 songs on it.  Touching upon genres as varied as Show Tunes, Adult Contemporary, Top 40 and Disco, I chose two dozen of the most heart-rending.  All are guaranteed to produce a lump in your throat, a tear in the eye.  So get a tissue ready as we immerse ourselves in a world of love gone wrong ...


  • You've Got to Learn/Nina Simone (1965) - This song is a primer on how to handle yourself with dignity after having your heart broken.  One of many songs on my list with a killer ending.  Excerpt: You've got to learn to leave the table when love's no longer being served.  To listen to the entire song double click here.




  • I'm Gonna Be Strong/Gene Pitney (1964) - Speaking of powerful endings, this one absolutely gives me the chills.  And I'm tearing up just typing the following lyrics:


I'll smile and say

Don't you worry, I'm fine

And you'll never know, darling

After you kiss me good-bye

How I'll break down and cryyyyyyyyyyyyyyy!


  • Nothing but Heartaches/The Supremes (1965) - What I really love about this song is the background vocals provided by Flo Ballard and Mary WilsonSong excerpt: The more that my love has grown, the less love he has shown.  He makes promises he don't keep; sometime I don't see him all week.  The clip I've chosen is a performance on the 1960s music show Hullabaloo.




  • I Get Along Without You Very Well - Composed in 1939 by Hoagy Carmichael, I wasn't aware of it until I heard it on Carly Simon's 1981 album Torch.  This is a song about trying to convince yourself that you're OK after a break up.
  • Not a Day Goes By - This is probably the best known song from the 1981 Sondheim musical Merrily We Roll Along.  Bernadette Peters' rendition at a tribute to Sondheim in London is powerfully beautiful.  It was another track found on Carly Simon's Torch LP. 




  • Can't Smile Without You/Barry Manilow (1978) - After a rather wimpy start the song builds to a satisfying climax.  Despairing excerpt: I can't smile without you, I can't laugh and I can't sing, I'm finding it hard to do anything.




  • I Don't Want to Walk Without You/Harry James & His Orchestra/vocal by Helen Forest (1942) - Yep, another song where the singer thought he'd do just fine without his former lover.  Woeful excerpt: Oh, baby, please come back or you'll break my heart for me, 'cause I don't want to walk without you no siree.




  • Say Something/Alex & Sierra (2013) - A beautiful ballad with mournful lyrics about walking away from a relationship.  The duo Alex & Sierra were winners of the X-Factor competition in 2013.  Heartbreaking excerpt: Say something, I'm giving up on you.  And I'm sorry that I couldn't get to you.
  • The One You Love/Glenn Frey (1982) - When this song, which starts with a great sax riff, was popular I was in the kind of relationship portrayed in it, i.e., the person I was dating was still in love with his ex, who treated him badly (in my case I eventually prevailed). 


Are you gonna stay with the one who loves you

Or are you going back to the one you love

Someone's gonna cry when they learn they've lost you

Someone's gonna thank the stars above  


  • Bluer Than Blue/Michel Johnson (1978) - Adult contemporary at its finest, this song tells the oft-told tale of someone trying to convince himself he's happy being single again, yet it's just not working out that way:


                I don't have to miss no TV shows

                I can start my whole life over

                Change the numbers on my telephone

                But the nights will sure be colder

                And I'm bluer than blue, sadder than sad ...


  • Cry/Godley & Creme (1985) - The music video for this song is in black & white and shows one crying face morphing into another (all of them rather homely).  It ends ends with anguished cries/howls.




  • Lead Me On/Maxine Nightngale (1979).  Maxine had a big disco hit in 1976 with Right Back to Where Started From, then three years later she scored with this plaintive ballad.  Forlorn excerpt: I'd rather be a fool with a broken heart than someone who has never had a part of you.
  • Shattered Dreams/Johnny Hates Jazz (1988) - The title of this top-10 hit from 1988 says it all.  However, because the band members are cute the pain of the lyrics is lessened somewhat.  Excerpt:  "I thought it was you who would do me no wrong.  But now all you've given me is shattered dreams." 




  • Tell Me on a Sunday - In this song the singer tells her lover how she'd prefer to be told about their break-up, i.e., gently rather than with high drama.  From the show Song and Dance, Bernadette Peters won the 1986 Tony Award for Best Actress in a Musical for her performance.  (Double click here to listen to Betty Buckley's version, which I think is stronger than Bernadette's.)




  • Everywhere I Go/Katharine McPhee (2007) - Ah, I've been there girlfriend.  This song tells the tale of a guy who dogged her around even though he was never really interested.  Sorrowful excerpt: So it annoys me you wasn't man enough, to come and tell me that I was never the one like you said I was.
  • But Not For Me - Written by George & Ira Gershwin for the 1930 musical Girl Crazy.  I've always got a kick from the clever wordplay at the end of the song: The climax to the plot should be a wedding knot, but there's no knot for me.  (There are a number of different endings to the song.)




  • Take Me in Your Arms/Kim Weston (1966) - This is my favorite.  It's fast tempo belies its desperately sad lyrics.  I remember tearing up while listening to it as I was running on the treadmill.  Eight years after Kim Weston's version, it got a rock treatment by the Doobie Brothers


I'm losing you and my happiness

My life is over, I must confess

I'll never, never see your smiling face no more

I'll never, never hear your knock on my door

Before you leave me, leave me behind

Let me feel happy just one more time

Take me in your arms

Rock me, rock me a little while - oh darling                       


  • Helpless - Another song of distress by Kim Weston, it was also covered by the Manhattan Transfer.  I'm amused by the song's use of the word "abusion", which I first thought was a made-up word.  Heartsick excerpt: Without a word, without a warning, you left my life one early morning.




  • I'd Rather/Luther Vandross (2002) - This song was first released as a ballad and later received a dance remix.  It tells the tale of a change of heart after a break up.  However, this appears to be somewhat of a tempestuous relationship. 


I'd rather have bad times with you

Than good times with someone else

I'd rather be beside you in a storm

Than safe & warm by myself

I'd rather have hard times together

Than to have it easy apart

I'd rather have the one who holds my heart


  • Hurt (1961) - Another song I was introduced to by Carly Simon's Torch album.  However, the original by Timi Yuro, which went to #4 on the Billboard Hot 100, is more powerful:


                I'm so hurt to think that you lied to me

                I'm hurt, way down deep inside of me

                You said your love was true

                And we'd never, ever part

                Now you want someone new

                And it breaks my heart


  • Losing My Mind - Another Sondheim classic, this one is from FolliesBarbara Cook performed it in the original 1970 production; when she was honored at the Kennedy Center Honors in 2011, Glenn Close sang it.  Written as a heartrending ballad, Liza Minnelli, in collaboration with the Pet Shop Boys, released a dance version of it in 1989.  Heart-wrenching excerpt: You said you loved me - or were you just being kind?  Or am I losing my mind?




  • I Who Have Nothing - Another classic ballad that got the disco treatment, this one by the legendary Sylvester in 1979.  Excerpt: I, I who have nothing.  I, I who have no one.


  • When Will I See You Again?/The Three Degrees (1974) - A fine example of Philly Soul, it tackles the time worn question that comes with dating.  I think it's one of the smoothest, slinkiest sad songs ever produced.  The video I've chosen, from a German TV show called Cultnacht is surreal.  Taking place in some sort of nightclub-like TV studio, the Aryan audience, drinking and smoking at their tables, is completely unresponsive to the performance.  Hilarious. 


                When will I see you again?

                When will our hearts beat together?

                Are we in love, or just friends?

                Is this my beginning or is this the end?


  • I Just Can't Get You Out of My Mind/The Four Tops (1973) - This  legendary R&B group had two dozen top 40 hits but this great song, inexplicably, isn't one of them.  I know of it thanks to the '60s Soul station on Sirius/XM Satellite Radio, which my summer share out in the Pines subscribed to.  The song tells the sad tale of a lover leaving without a trace and the maddening emptiness the bereft partner must contend with.  Choice exceprt: Oh it just ain't right what I'm going through.  Ten to one, I'm betting, there's no forgetting you.




Here are some other music-themed posts I've written the you might find interesting: 

Halston, Gucci, Fiorucci ... Favorite Disco Lyrics

Favorite Songs About New York - From a Gay Perspective

Silly Disco Songs - And What's Wrong With That?


























Rob, I can't remember the name of my favorite song, but the lyrics go something like this: "I love you too much to ever start liking you, so let's just let this story have an end", and ""..........don't expect me to be your friend." It's very gay because there are more lyrics about "seeing you in the Village with your latest friend." Maybe the group was Lobo?

Do you know the song?

Rob Frydlewicz

Dennis, you are correct. It was Lobo and the song is "Don't Expect Me to Be Your Friend". It was popular in the winter/spring of 1973 and peaked at #8 on the Billboard Hot 100.

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