When Keeping it Real Goes Wrong 

In the act of Keeping it Real, the outcome is unexpected and usually has a negative affect on the individual who decided to keep it real. (See Keeping it Real)

After losing his Job, Frank wrote a paper on, "When keeping it real goes wrong."

When Keeping it Real Goes Wrong by SouthParkChef August 18, 2008

when keeping it real goes wrong 

Chappelle show skit that satirizes a situation where a person decides to act on impulse or acts uninhibited by social mores or norms (i.e. "keeping it real") which usually leads to adverse and often times unexpected results.

When keeping it real goes wrong in a board meeting at your corporate job when someone mimics, coopts, or imitates your culture in a condescending way and seeks your affirmation in doing so. (i.e. "Give me some skin, dawg"). Also referred to as "actin' your color"

when keeping it real goes wrong by JNice007 March 2, 2009

When Keeping it Real Goes Wrong 

The greatest Chappelle's Show skit ever, self explanatory.

You think it's a game nigga? BAH BOW

When Keeping it Real Goes Wrong by General Crap March 7, 2004

When keeping it real goes wrong 

Rockets vs. Lakers game 1.

"The Rockets-Lakers game 1 was a bad episode of When Keeping it Real Goes Wrong!" - Stat Boy.

When keeping it real goes wrong by Richard Dean, Journalist April 19, 2004

When keepin it real goes wrong 

when keepin it real goes wrong is a hardcore song by the band emmure. you should listen to it.

i was moshing at the emmure concert yesterday when they played "when keepin it real goes wrong"

When keepin it real goes wrong by wagz0216 February 13, 2008