DMX - Damien Trilogy (1998-2001)

Dark Man X has plenty of tracks that could fit the bill for Halloween week, but I felt that his classic tale of him making a deal with the devil was the best choice.

The first verse opens with DMX lamenting his bad choices as a struggling rapper and wondering where his guardian angel is.  It's this point that the titular character pops up, promising him the world in return for some loyalty.  At this point X's desperation to succeed mixed with naivety sees him jump at the chance without thinking about it.  As the second verse goes on we hear Damien buttering DMX up nicely with cars, women and glory to the point that he's willingly pledging himself to Damien:

Got me pushing whips, taking trips across seas

Pockets stay laced, nigga I floss Gs

For that nigga I would bleed, give him my right hand

Now that I think about it, Yo, that's my man!

By the final verse, Damien starts calling in his favours, starting with X killing a few guys that Damien is beefing with... then some more... then some more.  DMX is ready to chill for a while but Damien isn't having it and keeps giving him more people to off, culminating in him telling X to kill one of his own friends

Aight fuck it, I'ma do it, who is it this time?

   Ayo remember that kid Sean you used to be with in '89

Naw that's my man

   I thought I was your man

But yo, that's my nigga!

  Hey, who's your biggest fan

  Either do it, or give me your right hand that's what you said

I see now, ain't nothin' but trouble ahead

X has eventually realised what he's got himself in for, but at this point it's too late and there's no way out and it's only gonna get worse.  

The song works brilliantly as a standalone song and it's a chilling story, but things get even darker in the sequels as Damien twists the knife even further and catches X in a vicious cycle of killing for him and then using those killings as leverage to make him do even more.

The Omen with Marilyn Manson is a particular standout for me and the instrumental on it is enough to give you bad dreams.  Easily the darkest of the three, here we see X determined to escape Damien's clutches but he keeps getting dragged back in by bad situations that probably wouldn't have occurred if he'd never met him in the first place.

By the third entry in the trilogy their relationship has become one of true hatred and is basically a back and forth showdown between the two leading to X turning to God to try and find a way out.

The story works on another level as a parallel to the typical gangster story we've seen in many movies, young guys getting dragged into the lifestyle for the promise of the glory without realising what they're sacrificing until it's much too late.  The more they try to escape, the worse it gets.