At first I tried getting songs that were of the aggressive side, since their first meeting wasn't pleasant, however I don't have much of the animosity songs that fit well with these two. So, like I did with the Sam/Ruby mix, I decided to go with a storyline with how I see their characters interacting.
01. "Into The Night" by Santana ft. Chad Kroeger
Dean's crossroads deal cannot be reversed, and he is not willing to take the chance. Now he has only a limited time left in this life before his soul is taken into the deep fiery pits, but that is until a young woman named Ruby shows up. Ruby just so happens to be a demon, who also says she's able to help him out with this deal. Dean is taken aback by this, thinking she’s tricking him, but as it turns out her words of helping him out are, indeed, sincere.
Like a gift from the heavens, it was easy to tell
It was love from above, that could save me from Hell
She had a fire in her soul, it was easy to see
How the Devil himself could be pulled out of me
02. "She's Got Balls" by AC/DC
Demons are always smart-mouthed and sarcastic, but there's something different about Ruby that isn't callous or ironic like all the other demons he's encountered. She challenges him, is fearless in the face of the Colt, and still manages to be selfless by saving their butts time after time. He's got to admit – this chick is pretty fierce. For, y'know, a demon chick.
She's got style that woman
Makes me smile that woman
She's got spunk that woman
She's got speed my lady
Got what I need babe
She's got the ability, hey
To make a man outta me
03. "Angry Angel" by Imogen Heap
Dean is the lost soul and Ruby is his angel, but Dean doesn’t want to be saved. Instead he goes on with life believing all will be fine. Ruby dislikes his stubbornness and tells him that she has every intention on saving his ass, and will do so no matter what it takes.
Over there stands my angry angel
And she's shaking her head, in disgrace with me
Yeah over there stands my angry angel
And she's frowning like hell, but I'm not feeling guilty
Over and over again, more and more for the pain
To release himself, from this shell
Time after time, you may glare at
Him for the way he looks like something drawn up from hell
04. "Burn The Witch" by Queens of the Stone Age
They are always getting persecuted for who and what they are; in this case, Dean learns Ruby's true identity and where demons originate from, and it's a cold hard truth he didn't really want to know. Or maybe he did.
Holding hands, skipping like a stone
On our way, to see what we have done
The first to speak, is the first to lie
The children cross,
Their hearts and hope to die
05. "Warning" by Incubus
She warns him, time and time again, about what is in store for him down in the pit. She knows all too well the pain and torment Hell has to offer, and despite her origins she sees herself in Dean, and she doesn’t want the same thing to happen to him.
When she woke in the morning
She knew that her life had passed her by.
And she called out a warning,
"Don't ever let life pass you by."
06. "Let The Flames Begin" by Paramore
There might not be a known way of saving Dean, but that's not stopping Ruby from taking action anyway. And now with finally coming to terms with not wanting to die, Dean isn't going to give up either. They'll fight and find a way, together.
Somewhere weakness is our strength,
And I'll die searching for it,
I can't let myself regret, such selfishness,
My pain I know the trouble caused, no matter how long
I believe that there's hope
Buried beneath it all and,
Hiding beneath it all and,
Growing beneath it all...