Sad songs are our lifeblood! I’m pretty sure our friendship was formed over weeping on our dorm room floors to “Lover I Don’t Have to Love” (note: see playlist, under “Bright Eyes”). So, in the spirit of Blue Monday and sharing our sorrows, we’ve created our definitive sad song playlist. Hilary has been waiting to use this playlist name since 2006 and finally has her chance! Stare out your window, lay on the floor, or open a bottle of wine and embrace the sadness.

Our Favourite Sad Selections


Friends used to joke that if I had a DJ night I would constantly be “slowing it down a bit.” I am guilty of stopping my friends from enjoying themselves at a party to cry with me to a recently discovered, devastatingly sad song. People rarely pass me the aux cord because of this sad song addiction. Here are some high/lowlights:

Left & Leaving – The Weakerthans

The Virtute the Cat songs make me cry the most, but I already posted them in our 2016 review. Instead, I opted for one that makes my heart ache. It reminds me of my formative years spent in Halifax. Moira & I listened to it while crossing the MacDonald Bridge into Dartmouth when moving out of our Henry Street apartment. Feelings.

“Memory will rust and erode into lists of all that you gave me:
a blanket, some matches, this pain in my chest,
the best parts of Lonely, duct-tape and soldered wires,
new words for old desires,
and every birthday card I threw away.
I wait in 4/4 time.
Count yellow highway lines that you’re relying on to lead you home.”

Chelsea Hotel #2 – Leonard Cohen

We lost him, but we still have all the beautiful words he wrote and sounds he created.

“You told me again you preferred handsome men
but for me you would make an exception.
And clenching your fist for the ones like us
who are oppressed by the figures of beauty,
you fixed yourself, you said, ‘Well never mind,
we are ugly but we have the music.’”

Upward Over the Mountain – Iron & Wine

Sam Beam’s voice ‘nuff said.

“Mother remember the night that the dog had her pups in the pantry
Blood on the floor and the fleas in their paws
And you cried ’til the morning”


Discontent and depression, cheating, and unrequited love are the things that always hit me where it hurts. Jenny always has my back for my go-to sad tracks. Best listened to in a car watching the world go by.

A Better Son/Daughter – Rilo Kiley

The perfect track to revel in and then fight self-loathing.

“And sometimes when you’re on
You’re really fuckin’ on
And your friends, they sing along and they love you
But the lows are so extreme
That the good seems fuckin’ cheap
And it teases you for weeks in its absence
But you’ll fight, and you’ll make it through
You’ll fake it if you have to
And you’ll show up for work with a smile”

Acid Tongue – Jenny Lewis

This one kills. When your fortune and your nature collide.

“And by the rolling river is exactly where I was
There was no snake oil cure for the unlucky in love
To be lonely is a habit, like smoking or taking drugs
And I quit them both, but man was it rough”

Slow Dancing in a Burning Room – John Mayer

He’s had my super sad heart since I was 16, but this track’s been making me weep for years.

“It’s not a silly little moment
It’s not the storm before the calm
This is the deep and dying breath of
This love that we’ve been working on.”


Welcome to Sad Town USA. Enjoy your visit. Weep, wallow, cry, bawl, sob, howl. Stare out the window, hide under the covers, drink some vodka, snuggle your cat – whatever you want. Come back anytime but just remember that we live here.

Note: The only song that makes me burst into uncontrollable sobs (yes, it has happened before) you’ll find down in Sarah’s picks below. Obviously, it’s a Ryan Adam’s song.

Landfill – Daughter

Every Daughter song is perfectly gut wrenching, sad and often relatable. But this song is epic and it bleeds. I wonder her hurt her though.

“So leave me in the cold
Wait until the snow covers me up
So I cannot move
So I’m just embedded in the frost
Then leave me in the rain
Wait until my clothes cling to my frame
Wipe away your tear stains
Thought you said you didn’t feel pain.”

Runner up: “Cause this is torturous electricity
Between both of us and this is
Dangerous ’cause I want you so much
But I hate your guts
I hate you”

Rogers Park – Justin Townes Earle

This song gives me #allthefeels and the piano is magical.

“I come here with hopes and
Guess I came here with dreams
Now I’m all alone I can’t even get to sleep
So take my heart and break it in
Send me back to the pines
Tired of lying awake at night
Feels like I’m running outta time
See my dreams before my eyes
Shadows on the wall
I ain’t got no place I can fall
Snowing in off the lake
Punching holes in the dark
Through the lonely streets
Of Rogers Park.”

Dear Chicago – Ryan Adams

OH DAVID RYAN ADAMS HOW I LOVE YOU. These lyrics give you the idea.

“Nothing breathes here in the cold.
Nothing moves or even smiles.
I’ve been thinking some of suicide.
But there’s bars out here for miles.
Sorry about the every kiss.
Every kiss you wasted (bad / back)
I think the thing you said was true,
 I’m going to die alone and sad.”


I know I’ve met a good sad song if I immediately want to learn it on guitar and play it quietly, alone in my room. It doesn’t get better than that. Here are a few favourites that always make me a little weepy:

Cover Me Up – Jason Isbell

This song isn’t actually sad, because it’s about finding your life partner and it’s truly beautiful. It’s just so goddamn touching, that I can’t listen to it without shedding a tear (also, watching this performance really gets me).

“And the old lovers sing ‘I thought it’d be me who helped him get home’
But home was a dream
One I’d never seen till you came along”

Basket – Dan Mangan

Holy shit, this whole song is devastating. If I ever needed to cry on command, I would just sing this in my head.

My bones are worn, my hip won’t hold
I used to be so young, how did I get so old?
Won’t you take my cane and hold my hand
You’re holding onto all I have
Just a basket full of memories
And I am losing more each day it seems
But if I can make it to the street
I’ll steal a car or a bike whatever there is to steal
And it might get cold I just don’t care
I’m going ’til I’m getting there
I’ll ride my steed all through this town
‘Til I have looked and I have found
Your peaceful memory
Won’t you return to me?
Won’t you return to me?

Runner up:

We are old
And our son took the dog away
And fair enough, guess we’re tired all the time
All the time
And you know dogs they need ample time outside

Call Me On Your Way Back Home – Ryan Adams

You may start listening to this song thinking, “This quiet lovely song isn’t so bad, I’m definitely not going to cry” — then the harmonica comes in. It cuts to my soul!

Call me on your way back home dear
Cause I miss you
And I just wanna die without you
Oh, I just wanna die without you
I just wanna die without you
Honey, I ain’t nothing new

Sorry and you’re welcome.