You can thank TheCatKing for this, because he's the one who asked me to do a breakdown for Cas's playlist.

Unfortunately some of his songs can't be explained in detail because their reason for inclusion is spoilery for books 2 or 3, but I will discuss what I can :)
_____________

PLAYLIST NAME: Prince of Perdition 

SONG ONE: Papaoutai by Stromae

Reason: Okay so this song's title translates basically to "Father where are you?" And if that's not a Cas mood then I don't know what is. He has a lot of daddy issues, which will be a recurring theme with his song selections.

Selected Lyrics: (The song is in French. I don't speak French, so the lyrics I reference are off a translation site. They may be slightly off the literal translation,  but the sentiment is there and that's what matters.)

Tell me where he comes from

Then I would know where I'm going

Mommy says when you look hard enough

You'll always end up finding it

......

Oh my dear father

Tell me where are you hiding?

I must've counted my fingers at least a thousand times

Where are you dad, where are you?

_____

SONG TWO: Chasing Rubies by Hudson Taylor

Reason: So this is "the Maggie song," which is pretty obvious if you read the lyrics. It's about his immediate infatuation with her, how rushed and shallow it is, as well as Cas's awareness of and insecurity with that fact. The instrumentation of the song hs a light playfulness to it that really compliments that feeling. 

Selected Lyrics: 

Take me away to someplace else

Cause I don't wanna see you, with anybody else

And maybe I'm selfish, I don't know

I hardly know you and I don't wanna let you go

......

What if you don't like me?

What if I'm being naive?

Maybe it's love, sure I don't know

I hardly know you and I don't wanna let you go

_____

SONG THREE: Numb by Linkin Park 

Reason: First of two Linkin Park songs on the playlist. It's my younger brother's favorite band so I listened to a LOT of their music while creating Cas's character and it sorta seeped in. I reigned myself into two when he originally had like, half Linkin Park, so be thankful. This is another one of his "daddy issues" songs, this one playing less into the "where the frick are you, father?" aspect and more into the "everyone wants me to live up to my father's legacy but I am Baby." 

Selected Lyrics: 

I'm tired of being what you want me to be

Feeling so faithless, lost under the surface

I don't know what you're expecting of me

Put under the pressure of walking in your shoes

Every step that I take is another mistake to you

.......

Can't you see that you're smothering me?

Holding too tightly, afraid to lose control

'Cause everything that you thought I would be

Has fallen apart right in front of you

And I know I may end up failing too

But I know you were just like me with someone disappointed in you

_____

SONG FOUR: Powerless by Linkin Park 

Reason: Ok, breaking away from "Cas is angsty about his dad" to check out its equally important sequel, "Cas is angsty about his sister" Can't talk about it in too much detail, but yeah, woof, Raini does a number on that poor boy in book two. 

Selected Lyrics: 

You hid your skeletons when I had shown you mine

You woke the devil that I thought you'd left behind

I saw the evidence, the crimson soaking through

Ten thousand promises, ten thousand ways to lose

......

I watched you fall apart and chased you to the end

I'm left with emptiness that words can not defend

You'll never know what I became because of you

Ten thousand promises, ten thousand ways to lose

And you held it all but you were careless to let it fall

You held it all and I was by your side, powerless

_____

SONG FIVE: A Deer Mistaking Candles for Headlights by Crywank

Reason: Being powerless, or rath Cas's perception of himself as powerless is a running theme throughout a lot of his music. Obviously the last song has it right there in the title, but this song has it permeated throughout every bit of the lyrics. This is basically Cas's internal dialogue, despite the cheerful and optimistic front he tries very hard to put on. 

Selected Lyrics: 

You can call me a coward and you'd be correct

Oh my neck is safely off the line

Now I'm keeping my mouth shut until this is over

Why bother speaking my mind?

You can call me a liar and that would be true

though I do disagree, I don't challenge you

I am docile and lazy, I show no respect

You can call me a coward and you'd be correct

......

Does the blank stare scare you more than the frown?

Am I the reason you feel down?

I am obsolete and apathetic, thoughtlessly apologetic

Watch my actions, or lack thereof, negate the person, I said I was.

.......

You could call me a Phony and I would agree

Oh I see the many versions of me that I perform

Molded to suit

I know the real me just convolutes

_____

SONG SIX: Carry On My Wayward Son by Sons of Serendip 

Reason: Breaking up the angst a bit with one hopeful song. I think of this as Amaranth's wish for Cas, that one day after all of this he'll find his place and purpose and voice. (Also lowkey me in my brain every time I write a scene about my soft sad boy.)

Selected Lyrics: 

Carry on my wayward son

For there'll be peace when you are done

Lay your weary head to rest

Don't you cry no more

.......

Don't you cry no more

Now your life's no longer empty

Surely heaven waits for you

_____

SONG SEVEN: Heel Turn 2 by The Mountain Goats

Reason: Say hello to Cas's absolute lowest point. I really can't say any more without going into spoiler territory. 

Selected Lyrics: 

Drift down into the new dark light without any reservations

You found my breaking point, Congratulations

Spent too much of my life now trying to play fair

Throw my better self overboard, shoot at him when he comes up for air

Come unhinged, get revenge

I don't want to die in here

.........

Stay good under pressure for years and years and years and years

Let all the trash rain down from way up in the rafters

I'm walking out of here in one piece, I don't care what comes after

Drive the wedge, torch the bridge

I don't want to die in here

_____

SONG EIGHT: Tripolar by MS MR

Reason: Staying vague, but this song is basically Cas deciding whether or not it is healthy or right for him to Stick This Out or if it would be better for him to do what he's been avoiding his entire life and Run Away. 

Selected Lyrics: 

On the surface everything is fine

But disaster struck behind these well-known lines

No more lies

Even in the blink of an eye, the chaos won't stand still

It's the terrible truth that hurts the most

Should I even stay?

It's the beautiful fool that gets too close

I'm here wasting away

.....

One two

It's getting too much for me to

Three four

Keep on chasing the throne

You know that it's the terrible truth that hurts the most

Trust when I say we'll find a remedy

_____

SONG NINE: King by Lauren Aquilina

Reason: Finally some real, genuine hopefulness! Brought to us from the PoV of Cas's endgame Love Interest. Without going into spoiler details while still expanding, this is basically Love Interest's wake up call/pep-talk to really get Cas to get his butt in gear and do what he needs to do to fix the Bad Things. This song is kinda hilariously soft compared to their actual dynamic, which would be more like: "Hey idiot, I love you but stop being so dumb."  

Selected Lyrics: 

You're alone, you're on your own

So what, have you gone blind

Have you forgotten what you have and what is yours?

There's method in my madness

There's no logic in your sadness

You don't gain a single thing from misery

Take it from me.

........

You've got it all, you lost your mind in the sound

There's so much more, you can reclaim your crown

You're in control, rid of the monsters inside your head

Put all your faults to bed

You can be King again.

_____

SONG TEN: What's Left of Me by Nick Lachey

Reason: The last song was endgame Love Interest to Cas, this song is Cas's reply to endgame Love Interest. While Love Interest is somewhat more abrasive, Cas really is a tender doof, so he would absolutely be the type to break out these Lyrics and genuinely mean them. 

Selected Lyrics: 

I've been dying inside, little by little

Nowhere to go but going out of my mind

In endless cirlcles

Running from myself until

You gave me a reason for standing still

........

Cause I want you, and I feel you

Crawling underneath my skin

Like a hunger, like a burning

To find the place I've never been

Now I'm broken and I'm fading

I'm half the man I thought I would be

But you can have what's left of me

________

Thoughts? Questions? Any other character you'd like to see the playlist for? Feel free to comment!

- Dino