This is said when talking with another person in a competitive manner, you concede that the other person has won.
It is usually said during one-up-manship contest.
Somewhat of a backwards "you win",but you really are the loser.
This is a very old saying...said as early as the 1800's.

Rhonda: I have a really bad headache.
Rick: Oh yeah, well I have a hangnail!
Rhonda: Yeah , and my knee hurts too.
Rick: Well, I guess "your ass is the blackest."

Your ass is the blackest by The_Overman September 8, 2007

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blackest way to die

When someone twerks so hard that their weave falls off, they slip on it, snap their neck and die

OH NO CHARLIE DONT TWERK! IT CAN CAUSE YOU TO SUFFER THE BLACKEST WAY TO DIE

ay yo niglet I hope miley cyrus suffers the blackest way to die

blackest way to die by SenorAndo June 19, 2014

The biggest blackest dick

A secret/rare white card from the popular card game Cards Against Humanity. The card can only be found in the lining of the top of "A Bigger Blacker Box", a box designed to store up to 1500 Cards Against Humanity cards. Unlike standard cards, the letters on the card, which read "The biggest blackest dick." are silver and are embossed into the card. The card is the successor to "A bigger blacker dick", the successor to "A big black dick".

Kyle: "Hey Jim, did you hear about the secret Cards Against Humanity card on reddit?"

Jim: "You must be talking about 'The biggest blackest dick.' Yeah I heard."

The biggest blackest dick by Encyclopedia Shitannica January 26, 2014

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