Music. It’s an intrinsic part of our lives. We use music to celebrate love. We use music to parade triumphs. But perhaps … out of all of life’s occasions … we rely on music the most to help us get through those times when we are most fragile; to help us cope through times in our lives when we yearn for someone to share in our pain and suffering. Specifically, heartbreak.

Now … you can deny it all you want, but I’m pretty sure that you couldn’t look me in the eyes and tell me that you’ve never had your heartbroken before; and I’ll double down on that bet by wagering that at least once in your life you got “misty eyed” when you heard a song play on the radio that reminded you of a lost-love or the “one who got away”.

As a “middle aged” (relatively speaking) single man, I’ve gone through my fair share of heartbreak. It being Valentine’s day, I’d like to share with you a few songs for “The Heartbroken”. These are recordings that live on my “breakup” playlist; songs that I’ve listened to to help me get past some pretty rough times. Some of the songs offer hope. Some of the songs offer empathy. Some of the songs simply offer a good sob … whatever … they’ve helped me in the past, and I figured I’d share them with you on this Valentine’s Day in case you’ve got some of those feels in you right now.

These are not ranked in any order, or organized by genre. Plus, I’ve got tons of other heart break songs… I mean Fleetwood Mac’s “Landslide”, Stevie Wonder’s “Lately”… the list can go on forever … but given that I decided to put this list together last minute, I just picked a nice mix. If you’ve got your own list, maybe you’ll add a tune or two after you check these out. Enjoy.

1. Brian McKnight’s “One Last Cry”

Brian McKnight has released a lot of powerful ballads that pull on the old heartstrings, but “One Last Cry”, which was released in 1991 on Brian McKnight’s self-titled debut album, is about as heart wrenching as they get. It is a teary, quiet storm ballad that bucked the trend of the New Jack Swing that was extremely popular at the time. Brian’s tender vocals over the gentle synths, sings of the pain associated with trying to move on from a love that was never meant to be. With it’s opening lyrics, “My shatter dreams and broken heart are mending on the shelf,” that pain is immediate. As he crescendos through the final chorus that he’ll only have “one last cry, before [he] leave[s] it all behind”, there’s a since of emotional confirmation that he is strong enough to get through this heart ache, only to send the song  off with his delicate falsetto with a “cry”.

One last cry
Before I leave it all behind
I’ve gotta put you out of my mind, this time
Stop living a lie.
I guess I’m down to one last cry.

2. Frank Sinatra’s “In The Wee Small Hours”

A few years ago, I wrote about an album that I thought was the most heart breaking album ever recorded. That album was Frank Sinatra’s “In The Wee Small Hours”. It was Old Blue Eye’s 9th studio album, recorded during a time when he himself was going through both personal and professional uncertainty. It has been regarded as music’s first “concept album”, filled with the themes of lost-love, introspection, melancholy and loneliness. Surely, several of the recordings off this album could have made my list, but the titled track is still my favorite.

When your lonely heart has learned its lesson,
You’d be hers if only she would call,
In the wee small hours of the morning,
That’s the time you miss her most of all.

3. Kings of Leon’s Cover of Robyn’s “Dancing On My Own”

When a friend told me that Kings of Leon covered Robyn’s “Dancing On My Own”, I kinda scoffed at the idea. But when I watched their live recording, and heard how they slowed the tempo down, I got it … and it hit me like a ton of bricks. When Caleb Followill wails the chorus of the song with his gravely voice, I was transported back to high school, reliving that of feeling jealous heartbreak ingrained in the lyrics.

I’m in the corner, watching you kiss her, oh oh oh
I’m right over here, why can’t you see me, oh oh oh
And I’m giving it my all, but I’m not the guy you’re taking home, ooh
I keep dancing on my own

4. Dionne Farris’ “Hopeless”

The 90’s was a great decade for motion picture soundtracks. One of my personal favorites, was the soundtrack to the motion picture “Love Jones”. Track number two on this album is “Hopeless” by Dionne Farris. On an album that featured tracks by Maxwell, Lauryn Hill, Cassandra Wilson and The Brand New Heavies, “Hopeless” was my favorite cut. Produced by Randy Jackson, Dionne’s supple voice searches for strength as the delicately played keys play a steady chord progression that consistently resolves to a consonance and then repeats itself, adding weight to the the “hopeless” feeling that Dionne sings about.

Hello yesterday
Remember how it used to be
Goodbye yesterday
I can’t take you with me

5. Jeff Buckley’s “Last Goodbye”

The last touch. The last kiss. The finality of what was.  This was Jeff Buckley’s “Last Goodbye”. While his cover of Leonard Cohen’s “Hallelujah” may have immortalized him in they eyes and ears of the public, this song , the second single from his album “Grace”, was, in my opinion, his most passionate studio recordings (there are some live, acoustic gems from his “Live in  Sin-e” that equally amazing, but that’s another conversation).

This recording has Jeff begging for his lover stay. One of my favorite lines of music ever written has Jeff pleading in his falsetto for one more kiss before she leaves, “[b]ut kiss [him] out of desire, babe, and not consolation”, but to no avail.

Well, the bells out in the church tower chime
Burning clues into this heart of mine
Thinking so hard on her soft eyes and the memories
Offer signs that it’s over… it’s over

6. Adele’s “Chasing Pavements”

Adele was the big winner at this year’s (2017) Grammys, but the song that I still feel is her best is off her debut album “19”: “Chasing Pavements”. Even before I heard her tell the story at The Wiltern about the song’s origins, I knew it was a song about her having her heart broken, and pondering the uncertainty of life after love. The song has added depth when you learn that she wrote the song after discovering that her boyfriend at the time had cheated on her, walking down the street alone and thinking to herself, “What is it you’re chasing? You’re chasing an empty pavement.”

Should I give up?
Or should I just keep on chasin’ pavements
Even if it leads nowhere?
Or would it be a waste
Even if I knew my place?
Should I leave it there?

7. Etta James’ “Fool That I Am”

One of my favorite female Blues/Soul voices is that of the inimitable Etta James. If you know anything about her life, you know that she did not live an easy one. The one time I saw her in concert at the Hollywood Bowl, she recalled a handful of the rough patches in her life, perhaps giving the audience a glimpse into where all of the passion in her singing comes from.

“Fool That I Am” is a simple song, with simple lyrics, but the weight of passion with which Ms. James sings this song can be felt weighing on your heart. As the melancholy strings intro the composition, we hear the soul of a woman who knows that love is lost, but just can’t let go.

Fool that I am,
For falling in love with you.
And a, fool that I am,
For thinking you loved me, too.

8. Derek And The Dominos’ “Bell Bottom Blues” 

The love triangle of Eric Clapton, George Harrison and Pattie Boyd (George Harrison’s wife) is the stuff of music legend, and it’s also some of Eric Clapton’s greatest source material. “Legend” has it that Pattie had asked Clapton to get her pair of bell-bottom blue jeans during one of his trips to the U.S.  He came back from that trip with, I’m assuming, those jeans and “Bell Bottom Blues”. This recording has so much pent up angst and anguish in it that when Clapton sings the pre-chorus and the chorus you can’t help but feel the same as proclaims:

Do you want to see me crawl across the floor to you?
Do you want to hear me beg you to take me back?
I’d gladly do it because
I don’t want to fade away.
Give me one more day, please.

9. Jason Mraz’s “Sleeping To Dream”

A lot of people think this is a love song. I won’t argue with them. I just see it/hear it differently. A woman I had been dating during law school introduced me to Jason Mraz. We went to a few Jason Mraz concerts. After a couple years, and due to life dealing me a pretty crappy (at the time) hand, we separated. Even though I was heartbroken, I would put this record on and it helped me go to sleep. Yeah … I was depressed, but at least I could be depressed listening to pretty, acoustic music, just telling me to fall asleep so I could dream. Le sigh.

It’s just a little a lullaby to keep myself from crying myself to sleep at night
Oh just a lullabye to keep from crying myself to sleep
[…]
Sleeping to dream about you
And I’m so tired
Of having to live without you
And I’m so tired

10. The Cure’s “Pictures of You”

This is my favorite The Cure song. It’s instrumentation is undeniably happy (heck, it was even used in a cheery television advertisement campaign for Kodak some years ago), but lyrically it is a romantically, melancholy poem about dealing with memories of past loves. Robert Smith’s straight forward vocal tones resonates throughout this recording embodying a vulnerability cloaked in confidence. This totality of this recording not only allows you to sulk in the mood, but it also gives you a faint glimmer of hope that maybe … just maybe … things will turn out okay in the end.

If only I’d thought of the right words
I could have held on to your heart
If only I’d thought of the right words
I wouldn’t be breaking apart
All my pictures of you

What you some of your favorite songs that have gotten you thought tough emotional patches? Leave them in the comments. I’d love to hear what you peeps listen to!