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Nails on a chalkboard 

(idiom) A sound that makes your ears bleed.
*plays an annoying song*

"This song is like nails on a chalkboard"

checkerboard 

Southwest Airlines equivalent of SSSS (see previously accepted definition highlighted) . Upon receiving the checkerboard you have to go through extensive secondary security screening because of pre-selected criteria.
Due to me flying one-way, I was given the checkerboard treatment by Southwest. Now I have to go through extensive security before the flight.
checkerboard by Piranha January 26, 2006

checkerboard chick 

Either a black girl who is with a white boy or visa versa, a white girl with a black boy.
"My boyfriend is as black as night and I'm ivory. I am a checkerboard chick."

North of the checkerboard 

An area to the north of Wiarton, Ontario, on the Bruce Peninsula, renowned for rednecks and peculiar behaviour.
Yeah, he's from north of the checkerboard.

chessboard 

A friendship between a white person and a black person which is so awesome that experts can't explain it.
Notable examples include J.D. and Turk from Scrubs, Shawn and Gus from Psych, Riggs and Murtagh from the Lethal Weapon series.
Daniel: Henry my black friend you are so awesome
Henry: And you too, my white friend Daniel
Daniel: We are so awesome. Like a chessboard!
chessboard by InspectorNoir November 5, 2012

Cockboarding 

The art of leaving drawings of cocks on whiteboards and posters in the office to be found by your work colleagues. These are sometimes hidden by other office items for impact when found e.g. whiteboard erasers.
Man, you have been cockboarding all over the office and it's hilarious.
Cockboarding by DeLeaCious October 21, 2015