Jay-Z - "Regrets"

If New York is indeed hip hop's Mecca, then Jay-Z's Reasonable Doubt is certainly one of the movement's holy texts.  From his verbal duel with Biggie on "Brooklyn's Finest" to his contemplation of the price of success on "D'Evils," the wordplay throughout Shawn Carter's debut is, well, Unreasonable.  A classic from top-to-bottom, Doubt was the landmark album for Mafioso rap--the one that best paralleled Scarface's story from rise to fall.  While I have a hard time picking a favorite song from the album, the last official track (before bonus tracks) certainly numbers among the best.  "Regrets" marks the downfall of the anti-hero and presents us with advice that is applicable to any walk of life, while simultaneously beautifully critical of the American Dream:

You used to hold me, told me that I was the best,
Anything in this world I want I could possess.
All that made me want is all that I could get,
In order to survive, gotta learn to live with regrets.


Peace, Love, & Hova,
WordIsBorn

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