Jay-Z - Regrets (1996)

As sure as this, Earth is turning, souls burning
In search of higher learning
Turning in every direction, seeking direction
My mom's crying because her insides are dying
Her son trying her patience, keep her heart racing
A million beats a minute, I know I push you to your limit
But it's this game, love, I'm caught up all in it
They make it so you can't prevent it
Never give it, you gotta take it
Can't fake it, I keep it authentic
My hand got this pistol shaking, cause I sense danger
Like Camp Crystal Lake and
Don't wanna shoot him, but I got him trapped
Within this infrared dot, about to hot him and hit rock bottom
No answers to these trick questions, no time shit's stressing
My life found, I got to live for the right now
Time waits for no man, can't turn back the hands
Once it's too late, gotta learn to live with regrets

Jay-Z's Reasonable Doubt (without a doubt one of the greatest rap records of all time) is often credited for popularizing so-called Mafioso rap (wherein the artist dons --pun intended-- the persona of a mob boss).  And while there are more than a few moments where Jay-Z glamorizes that lifestyle (see, e.g., Can't Knock the Hustle, Cashmere Thoughts and, to a lesser extent, Can I Live?), he doesn't shy away from meditating on the dark side, as well.

This is the number one rule for your set
In order to survive got to learn to live with regrets
On the rise to the top many drop, don't forget
In order to survive got to learn to live with regrets