Top Five Songs ... 03.15.2019
DFM Masthead Disenfranchised FM Cuckoo's Eleven Top Five Songs Armchair Producer Music MD Tin Cans Scratch Take Life and Times Input


Last month, I featured the top five songs for a best kiss. But the only topic music covers more frequently than the intoxication of love is the devastation that follows when love ends. Heartbreak is an acute pain, yet it feels like it will never go away. And many believe that without feeling heartbreak, one can never truly appreciate love. It's cruel that we can be subjected to it at such an early age. Adolescence is tough enough already, but to add the emotional gut-punch to an already tender soul renders everything else in life meaningless. It feels like we'll never make it through to the other side, no matter how others may try to comfort you. Because how can you relate to someone who doesn't emote the same level of devastation that you feel? This, of course, is where music steps in to play the part.

I hinted back in January that some top five posts will feature guests. Given how subjective heartbreak (and its corresponding soundtrack) can be, what better time to introduce our first guest writer than now? I met Dan McKernan in fourth grade, which for those playing at home, is a really long time ago. Our lunchtime conversations at Pare Elementary School often consisted of music debates. While the balance of the class discussed the merits of Bon Jovi and Ratt, Dan and I debated topics like Beach Boys versus the Beatles. Dan's passion for music has never waned, whether it's critique of my music lists or playing with his band, The 44 Territories. You should check them out, because then I can guilt Dan into letting me sing a song with them.

I mentioned before that heartbreak is subjective, so Dan and I agreed on a few parameters to keep it tight. Here's a synopsis of our chat:

Matt: First, no Beatles or Stones. Sorry.
Dan: This doesn't bother me. Neither the Beatles nor Stones are known as great personal storytellers, and a great heartbreak song has to feel intensely personal.
Matt: I can tell you that I'm feeling intensely personal right now ...
Dan: I'm not sure that one of their songs would make my Top 100 for this topic (unless it was the heartbreak Keith felt getting off smack).
Matt: Maybe we should move on ... must appear on an album, single, or b-side. No live unreleased versions.
Dan: Any worthwhile song should be a real release.
Matt: Heartbreak is defined as: broken heart due to unrequited love, not the passing of someone
Dan: Now we get into trouble. George Jones' "He Stopped Loving Her Today" would've been a pick.
Matt: That's what you get for the comments about Keef. And I'm not even done with the definition yet.
Dan: I am already regretting this.
Matt: Heartbreak is the period of wallow and self-loathing, not the goddammit-I'm-taking-no-prisoners.
Dan: I can respect this, since the "Get behind me, Satan!" list should be separate. These songs should make you want to pick up the phone ...
Matt: No matter what time ...
Dan: Right, and beg for forgiveness for everything you've ever done wrong. They should reduce you to ugly crying in your car, delaying your order at the pick-up window for at least 30 seconds. In a moment of need, they should lend themselves to being played over and over for a period of hours (or even days).
Matt: I knew you were the right person for this. Should we actually do this over lunch, and if so ... are you gonna eat that dessert?
Dan: Some things never change ...

Have I mentioned that we've known each other for over thirty years? ANYWAY, let's get on the lists, which we will neither confirm nor deny having ever listened to in prior states of heartbreak ...

Honorable Mention

Matt's Picks

Dan's Picks

New Radicals - "Someday We'll Know" [1998] Willie Nelson - "The Scientist" [2002]

"So many questions
I need an answer
Two years later you're still on my mind."

"Tell me you love me, come back and haunt me."

A lot of people forget this group had a follow-up to "You Get What You Give" and consider them a one-hit wonder. That's heartbreaking. Don't mind my dad humor ... it's self-defense for hypothetically listening to this song about ten thousand times in days of yesteryear. The narrator is still gutted after all this time, and while they may be in a better place, they're still longing for that person to be with them.

Admittedly, I thought this song was good when Coldplay did it, but when Willie Nelson cut the song a few years later (Chipotle commercial aside), I felt it really hit legendary status. Any good breakup involves that moment of wondering "what happened to us?" This song gets it.

Adele - "Someone Like You" [2011] Otis Redding - "I've Been Loving You Too Long (To Stop Now)" [1965]

"I hate to turn up out of the blue, uninvited
But I couldn't stay away, I couldn't fight it
I had hoped you'd see my face
and that you'd be reminded that for me, it isn't over."

"You are tired and you want to be free
My love is growing stronger, as you become a habit to me."

I really want to rank this song higher, but I'm handcuffed by my own definitions. Adele has suggested in interviews that "Rolling in the Deep" and this song are intended to complement one another, with the former viewed in the present and the latter viewed sometime in the distant future. It's a level of acceptance and well-wishing that she expected to carry at some point, so for that reason, it shouldn't make the list. However, because she wrote it at the same time she held the feeling in "Rolling," you can hear the pain in her voice, so it's worth including in honorable mention.

One of Otis' best, this is just 3:00 of pure, unadulterated pleading. The sound of desperation, in a sould package that features not only Booker T and the MGs, but the Bar-Kays and Issac Hayes behind him. She had to come back, right?

Bill Withers - "Ain't No Sunshine" [1971]

"And I know, I know, I know, I know, I know, I know, I know, I know,
I know, I know, I know, I know, I know, I know, I know, I know, I know,
I know, I know, I know, I know, I know, I know, I know, I know, I know."

Matt: I love that we only have one song that's on both of our lists, and I love it even more that it's this one. This would've been a really good song with a proper third verse, but went from good to great once Booker T, Graham Nash, and Steven Stills suggested that Withers keep the "I know" placeholder. I bet we could ask twenty random people on the street: many wouldn't recognize the name Bill Withers, but every one of them would recognize this verse.

Dan: Short and to the point, it's an oft-covered classic. Can't say it any better than that third verse.

Matt's Picks

Dan's Picks

Led Zeppelin - "Your Time Is Gonna Come" [1969] The Cure - "Pictures Of You" [1989]

"Lying, cheating, hurting
That's all you seem to do
Messin' around with every guy in town
Holding me down for thinking of someone new."

"There was nothing in the world that I ever wanted more
than to feel you deep in my heart
There was nothing in the world that I ever wanted more
than to never feel the breaking apart."

I'll never forget the first time I heard this song: I was hanging out in my dorm room, and as soon as the song began playing, my friend told quite possibly the best wingman story I've heard: my friend Scotty broke up with his high school girlfriend, with whom he shared a locker. Scotty's friend picked him up for school a six o'clock the next morning so that he could clean out the locker without running into his ex. And he had this song cued up to play as soon as Scotty got into the car. I immediately folded this song into my music library for reasons of heartbreak.

From the kings of gloomy, "Pictures of You" isn't just sad lyrics: the entire song, music and all, sounds like enveloping sadness. Yet, it remains incredibly listenable. Anyone who's gone through a tumultuous breakup knows that feeling of being left with the photos of better times. I highly recommend the album cut from the masterpiece Disintegration over the single edit.

Fleetwood Mac - "Landslide" [1975] Jeff Buckley - "Last Goodbye" [1994]

"Well, I've been afraid of changing
'Cause I've built my life around you."

"I hate to feel the love between us die."

Much has been said about the tumultuous relationship between the woman with a man's name and the man with a woman's name. There are honestly a few that could've made the list. But it's the torturous lyrics that make this song the right choice: should chain herself down or should she allow them to go separate ways?

OK, this album may be one of the best end-to-end breakup albums ever, but I think of "Last Goodbye" as its high point (over "Hallelujah"). It has been pointed out that this may actually be an I'm dumping you song, but that seems inconclusive at best. That said, it's enough to bump it down to 6th man on the roster.

Those are some heavy songs. But I don't think we've reached gut-punch level quite yet. Buckle up, because as Dan would say, we're heading into ugly crying territory.

Top Five Songs

Matt's Picks

Dan's Picks

NUMBER FIVE: Sam Cooke - "Bring It On Home" [1962] NUMBER FIVE: Bonnie Raitt - "I Can't Make You Love Me" [1991]

"I know I laughed when you left
but now I know I only hurt myself."

"I'll close my eyes, then I won't see
the love you don't feel when you're holding me."

The instant you hear the heavy gospel influence of the piano and drumming, you know that the lyrics won't be far behind ("If you should ever change your mind / about leaving, leaving me behind"). If you don't feel the heartache within the first ten seconds of this song, you're inhuman.

This is the sound of unrequited love incarnate. Lyrics, vocals, the sadness of the production ... probably the best example of the inherent sadness still present in that last stage of grief: acceptance.

NUMBER FOUR: Elvis Costello - "Alison" [1977] NUMBER FOUR: Isaac Hayes - "Walk On By" [1969]

"I'm not going to get too sentimental
Like those other sticky valentines
'Cause I don't know if you were loving somebody
I only know it isn't mine."

"You put the hurt on
You socked it to me, Momma."

To everyone who's ever heard the phrase, "I'm not interested in seeing anyone right now," and then eventually reaching the conclusion that the person is really saying, "I'm not interested in you."

OK, this song is a jam, flat-out. The strings, the drums, that bad-ass guitar ... there's a reason this song has been sampled about a million times. But under it all is the most masterful version of a Burt Bacharach song. When Dionne Warwick did this tune, it was a poppy confection. In the hands of Black Moses, it becomes a gut-wrenching song of pleading and sorrow.

NUMBER THREE: The Police - "Every Breath You Take" [1983] NUMBER THREE: The Band - "It Makes No Difference" [1975]

"Since you've gone I've been lost without a trace
I dream at night I can only see your face
I look around, but it's you I can't replace
I feel so cold and I long for your embrace."

"It makes no difference how far I go
Like a scar, the hurt will always show
And it makes no difference who I meet
They're just a face in the crowd on a dead-end street."

Written at the same desk in Jamaica where Ian Fleming wrote his 007 novels (!), this song has a lot of baggage. Sting wrote this after taking massive heat for leaving his wife for their next-door neighbor. Sting and Stewart Copeland hated each other by that point, and The Police were literally fist-fighting in the studio. It's a miracle this song ever saw the light of day. It's Copeland's guitar riff that gives the song wings. By the moment you reach the bridge, there's a lift-off to new levels of heartache and self-loathing.

A dark horse since this wasn't a hit, but between Rick Danko's fragile, quivering voice, Robbie Robertsons' searing guitar, and the sax solos, this song emphasizes the break in heartbreak. These lyrics are poetry, and the live performance of Scorcese's The Last Waltz ups the ante a full notch, too.

NUMBER TWO: Sinead O'Connor - "Nothing Compares 2 U" [1990] NUMBER TWO: Adele - "Someone Like You" [2011]

"It's been seven hours and fifteen days."

"I hate to turn up out of the blue, uninvited
But I couldn't stay away, I couldn't fight it
I had hoped you'd see my face
and that you'd be reminded that for me, it isn't over."

Normally, when you mentioned the words "Prince" and "cover" together, it's about how he slayed a song (like this. Or this. Or this). But I can't think of a soul who's ever felt sorry for him after listening to his version of this song. O'Connor's vocals are essential: You can feel the desperation: in the opening lyric, and in the retort to her doctor.

Simple and irrefutable. Ugly crying everywhere.

NUMBER ONE: Etta James - "I'd Rather Go Blind" [1968] NUMBER ONE: Derek and the Dominos - "Layla" [1970]

"Something deep down in my soul said, 'Cry Girl'."

"Let's make the best of the situation
Before I finally go insane
Please don't say we'll never find a way
And tell me all my love's in vain."

The moment the narrator eyes her man walking with another woman, she knows their relationship is only a matter of time. And like her relationship, the moment we hear the opening guitar lick we know that this is a song expressing the deepest pains of love. And yet, there's something else that makes this song timeless: the narrator's straightforward expression of sadness allows instant empathy. We've all been there, whether it was five days or five decades ago. It's hard to top Don Draper when it comes to expressing how raw our memories can be, but Etta James does just that. It's a song so powerful that it can trigger the memories of heartbreak, yet over time balances with an appreciation to have lived through the moment, and to be there for others when they experience their heartbreak. In actuality, we can relate to each other's despair. Sometimes, we just need a flashback to do so.

This entire album is Clapton's ode to Patti Harrison. Track by track, it documents his playing at its best and his longing at its worst. This song is classic, of course, but don't sleep on "Bell Bottom Blues." The guitar playing by Duane Allman is transcendent. And, hey, it must've worked, because Patti eventually left George for Clapton. Hope for us all, I guess.

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